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7-Night Caribbean (Caribbean - All) |
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Ports of Call: Philipsburg, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg
Departs: Sun. 1/4/26
Returns: Sun. 1/11/26
Nights: 7
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On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all...
 Expand On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms, Wind Surf renovation now brings you some of the most beautiful public spaces at sea.  Collapse |
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Special Sale: Travel Is Better When You're All-In (view details)
7-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: Complimentary All-Inclusive Package on sailings through March 2026 Booking Window: Now - 11/15/25 Applicable Sailings: All sailings through 3/31/26 Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) for voyages through March 31, 2026. All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made. This offer cannot be applied retroactively. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer expires on November 15, 2025. Ships’ registry: Bahamas.
7-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: All-Inclusive Package + Up to $200 Onboard Credit per stateroom + Save 5% when you pay in full Booking Window: Now - 10/31/25 Applicable Sailings: Star Breeze and Wind Star 2027 Tahiti voyages. Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages. Terms & Conditions: For Windstar’s newly released Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for 2026/2027 Caribbean and Latin America voyages. Ships’ registry: Bahamas. For Windstar’s newly released Star Breeze and Wind Star 2027 Tahiti voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Consult your Windstar representative for promotional offer or discount combinability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for Tahiti Star Breeze and Wind Star voyages. Ships’ registry: Bahamas.
7-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: Up to $1,000 Onboard Credit per stateroom on sailings through March 2026 Offer Details:
Booking Window: Now - 10/7/25 Applicable Sailings: All sailings through March 2026 Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) and up to $1,000 Onboard Credit per suite ($500 per guest) for all sailings through March 31, 2026. |
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14-Night Caribbean (Caribbean - All) |
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Ports of Call: Philipsburg, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg, Basseterre, Little Bay, Gustavia, Pointe a Pitre, Roseau, Pigeon Island, Bridgetown
Departs: Sun. 1/4/26
Returns: Sun. 1/18/26
Nights: 14
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On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all...
Expand On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms, Wind Surf renovation now brings you some of the most beautiful public spaces at sea. Collapse |
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Special Sale: Travel Is Better When You're All-In (view details)
14-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: Complimentary All-Inclusive Package on sailings through March 2026 Booking Window: Now - 11/15/25 Applicable Sailings: All sailings through 3/31/26 Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) for voyages through March 31, 2026. All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made. This offer cannot be applied retroactively. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer expires on November 15, 2025. Ships’ registry: Bahamas.
14-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: All-Inclusive Package + Up to $200 Onboard Credit per stateroom + Save 5% when you pay in full Booking Window: Now - 10/31/25 Applicable Sailings: Star Breeze and Wind Star 2027 Tahiti voyages. Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages. Terms & Conditions: For Windstar’s newly released Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for 2026/2027 Caribbean and Latin America voyages. Ships’ registry: Bahamas. For Windstar’s newly released Star Breeze and Wind Star 2027 Tahiti voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Consult your Windstar representative for promotional offer or discount combinability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for Tahiti Star Breeze and Wind Star voyages. Ships’ registry: Bahamas.
14-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: Up to $1,000 Onboard Credit per stateroom on sailings through March 2026 Offer Details:
Booking Window: Now - 10/7/25 Applicable Sailings: All sailings through March 2026 Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) and up to $1,000 Onboard Credit per suite ($500 per guest) for all sailings through March 31, 2026. |
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21-Night Caribbean (Caribbean - Extended) |
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Ports of Call: Philpsburg, Falmouth, Road Bay, Sopers Hole, Great Harbour, Jost Van Dyke BVI (2 Days), Gustavia, Philpsburg, Basseterre, Gustavia, Terre-de-Haut, Mayreau, Kingstown, Bridgetown, Trois Ilets, Castries, Pigeon Island (2 Days), Port Elizabeth, Bequia, Mayreau, Saint George's, Bridgetown
Departs: Sun. 1/4/26
Returns: Sun. 1/25/26
Nights: 21
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On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all...
Expand On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms, Wind Surf renovation now brings you some of the most beautiful public spaces at sea. Collapse |
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Special Sale: Travel Is Better When You're All-In (view details)
21-Night Caribbean (Caribbean - Extended)Wind Surf Windstar Cruises Offer: Complimentary All-Inclusive Package on sailings through March 2026 Booking Window: Now - 11/15/25 Applicable Sailings: All sailings through 3/31/26 Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) for voyages through March 31, 2026. All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made. This offer cannot be applied retroactively. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer expires on November 15, 2025. Ships’ registry: Bahamas.
21-Night Caribbean (Caribbean - Extended)Wind Surf Windstar Cruises Offer: All-Inclusive Package + Up to $200 Onboard Credit per stateroom + Save 5% when you pay in full Booking Window: Now - 10/31/25 Applicable Sailings: Star Breeze and Wind Star 2027 Tahiti voyages. Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages. Terms & Conditions: For Windstar’s newly released Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for 2026/2027 Caribbean and Latin America voyages. Ships’ registry: Bahamas. For Windstar’s newly released Star Breeze and Wind Star 2027 Tahiti voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Consult your Windstar representative for promotional offer or discount combinability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for Tahiti Star Breeze and Wind Star voyages. Ships’ registry: Bahamas.
21-Night Caribbean (Caribbean - Extended)Wind Surf Windstar Cruises Offer: Up to $1,000 Onboard Credit per stateroom on sailings through March 2026 Offer Details:
Booking Window: Now - 10/7/25 Applicable Sailings: All sailings through March 2026 Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) and up to $1,000 Onboard Credit per suite ($500 per guest) for all sailings through March 31, 2026. |
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22-Night Caribbean (Caribbean - Extended) |
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Ports of Call: Philipsburg, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg, Basseterre, Gustavia, Little Bay, Gustavia, Deshaies, Roseau, Pigeon Island, Bridgetown, Grande Anse, Castries, Pigeon Island, Admiralty Bay, Bequia, Mayreau, St. George's, Bridgetown
Departs: Sun. 1/4/26
Returns: Mon. 1/26/26
Nights: 22
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On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all...
Expand On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms, Wind Surf renovation now brings you some of the most beautiful public spaces at sea. Collapse |
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Special Sale: Travel Is Better When You're All-In (view details)
22-Night Caribbean (Caribbean - Extended)Wind Surf Windstar Cruises Offer: Complimentary All-Inclusive Package on sailings through March 2026 Booking Window: Now - 11/15/25 Applicable Sailings: All sailings through 3/31/26 Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) for voyages through March 31, 2026. All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made. This offer cannot be applied retroactively. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer expires on November 15, 2025. Ships’ registry: Bahamas.
22-Night Caribbean (Caribbean - Extended)Wind Surf Windstar Cruises Offer: All-Inclusive Package + Up to $200 Onboard Credit per stateroom + Save 5% when you pay in full Booking Window: Now - 10/31/25 Applicable Sailings: Star Breeze and Wind Star 2027 Tahiti voyages. Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages. Terms & Conditions: For Windstar’s newly released Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for 2026/2027 Caribbean and Latin America voyages. Ships’ registry: Bahamas. For Windstar’s newly released Star Breeze and Wind Star 2027 Tahiti voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Consult your Windstar representative for promotional offer or discount combinability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for Tahiti Star Breeze and Wind Star voyages. Ships’ registry: Bahamas.
22-Night Caribbean (Caribbean - Extended)Wind Surf Windstar Cruises Offer: Up to $1,000 Onboard Credit per stateroom on sailings through March 2026 Offer Details:
Booking Window: Now - 10/7/25 Applicable Sailings: All sailings through March 2026 Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) and up to $1,000 Onboard Credit per suite ($500 per guest) for all sailings through March 31, 2026. |
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28-Night Caribbean (Caribbean - All) |
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Ports of Call: Philipsburg, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg, Basseterre, Little Bay, Gustavia, Pointe a Pitre, Roseau, Pigeon Island, Bridgetown, Grande Anse, Castries, Pigeon Island (2 Days), Admiralty Bay, Bequia, Mayreau, St. George's, Bridgetown, Man-O-War, Tobago, Mayreau, Soufriere Bay, Kralendijk, Bonaire, Willemstad, Oranjestad
Departs: Sun. 1/4/26
Returns: Sun. 2/1/26
Nights: 28
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On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all...
Expand On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms, Wind Surf renovation now brings you some of the most beautiful public spaces at sea. Collapse |
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Special Sale: Travel Is Better When You're All-In (view details)
28-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: Complimentary All-Inclusive Package on sailings through March 2026 Booking Window: Now - 11/15/25 Applicable Sailings: All sailings through 3/31/26 Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) for voyages through March 31, 2026. All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made. This offer cannot be applied retroactively. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer expires on November 15, 2025. Ships’ registry: Bahamas.
28-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: All-Inclusive Package + Up to $200 Onboard Credit per stateroom + Save 5% when you pay in full Booking Window: Now - 10/31/25 Applicable Sailings: Star Breeze and Wind Star 2027 Tahiti voyages. Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages. Terms & Conditions: For Windstar’s newly released Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for 2026/2027 Caribbean and Latin America voyages. Ships’ registry: Bahamas. For Windstar’s newly released Star Breeze and Wind Star 2027 Tahiti voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Consult your Windstar representative for promotional offer or discount combinability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for Tahiti Star Breeze and Wind Star voyages. Ships’ registry: Bahamas.
28-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: Up to $1,000 Onboard Credit per stateroom on sailings through March 2026 Offer Details:
Booking Window: Now - 10/7/25 Applicable Sailings: All sailings through March 2026 Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) and up to $1,000 Onboard Credit per suite ($500 per guest) for all sailings through March 31, 2026. |
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55-Night Caribbean (Caribbean - Extended) |
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Ports of Call: Philipsburg, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg, Basseterre, Little Bay, Gustavia, Pointe a Pitre, Roseau, Pigeon Island, Bridgetown, Grande Anse, Castries, Pigeon Island (2 Days), Admiralty Bay, Bequia, Mayreau, St. George's, Bridgetown, Man-O-War, Tobago, Mayreau, Soufriere Bay, Kralendijk, Bonaire, Willemstad, Oranjestad, Santa Marta, Cartagena, Bocas Del Toro, Colon (2 Days), Bocas Del Toro, San Andres Island, Roatan, Belize City, Costa Maya, Cozumel, Grand Cayman, Cayman Brac, Port Antonio, Santo Domingo, La Romana, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, Philipsburg
Departs: Sun. 1/4/26
Returns: Sat. 2/28/26
Nights: 55
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On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all...
Expand On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms, Wind Surf renovation now brings you some of the most beautiful public spaces at sea. Collapse |
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Special Sale: Travel Is Better When You're All-In (view details)
55-Night Caribbean (Caribbean - Extended)Wind Surf Windstar Cruises Offer: Complimentary All-Inclusive Package on sailings through March 2026 Booking Window: Now - 11/15/25 Applicable Sailings: All sailings through 3/31/26 Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) for voyages through March 31, 2026. All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made. This offer cannot be applied retroactively. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer expires on November 15, 2025. Ships’ registry: Bahamas.
55-Night Caribbean (Caribbean - Extended)Wind Surf Windstar Cruises Offer: All-Inclusive Package + Up to $200 Onboard Credit per stateroom + Save 5% when you pay in full Booking Window: Now - 10/31/25 Applicable Sailings: Star Breeze and Wind Star 2027 Tahiti voyages. Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages. Terms & Conditions: For Windstar’s newly released Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for 2026/2027 Caribbean and Latin America voyages. Ships’ registry: Bahamas. For Windstar’s newly released Star Breeze and Wind Star 2027 Tahiti voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Consult your Windstar representative for promotional offer or discount combinability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for Tahiti Star Breeze and Wind Star voyages. Ships’ registry: Bahamas.
55-Night Caribbean (Caribbean - Extended)Wind Surf Windstar Cruises Offer: Up to $1,000 Onboard Credit per stateroom on sailings through March 2026 Offer Details:
Booking Window: Now - 10/7/25 Applicable Sailings: All sailings through March 2026 Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) and up to $1,000 Onboard Credit per suite ($500 per guest) for all sailings through March 31, 2026. |
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7-Night Caribbean (Caribbean - All) |
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Ports of Call: Philipsburg, Basseterre, Little Bay, Gustavia, Deshaies, Roseau, Pigeon Island, Bridgetown
Departs: Sun. 1/11/26
Returns: Sun. 1/18/26
Nights: 7
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On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all...
Expand On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms, Wind Surf renovation now brings you some of the most beautiful public spaces at sea. Collapse |
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Special Sale: Travel Is Better When You're All-In (view details)
7-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: Complimentary All-Inclusive Package on sailings through March 2026 Booking Window: Now - 11/15/25 Applicable Sailings: All sailings through 3/31/26 Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) for voyages through March 31, 2026. All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made. This offer cannot be applied retroactively. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer expires on November 15, 2025. Ships’ registry: Bahamas.
7-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: All-Inclusive Package + Up to $200 Onboard Credit per stateroom + Save 5% when you pay in full Booking Window: Now - 10/31/25 Applicable Sailings: Star Breeze and Wind Star 2027 Tahiti voyages. Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages. Terms & Conditions: For Windstar’s newly released Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for 2026/2027 Caribbean and Latin America voyages. Ships’ registry: Bahamas. For Windstar’s newly released Star Breeze and Wind Star 2027 Tahiti voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Consult your Windstar representative for promotional offer or discount combinability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for Tahiti Star Breeze and Wind Star voyages. Ships’ registry: Bahamas.
7-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: Up to $1,000 Onboard Credit per stateroom on sailings through March 2026 Offer Details:
Booking Window: Now - 10/7/25 Applicable Sailings: All sailings through March 2026 Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) and up to $1,000 Onboard Credit per suite ($500 per guest) for all sailings through March 31, 2026. |
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14-Night Caribbean (Caribbean - All) |
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Ports of Call: Philipsburg, Basseterre, Little Bay, Gustavia, Deshaies, Roseau, Pigeon Island, Bridgetown, Grande Anse, Castries, Pigeon Island (2 Days), Admiralty Bay, Bequia, Mayreau, St. George's, Bridgetown
Departs: Sun. 1/11/26
Returns: Sun. 1/25/26
Nights: 14
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On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all...
Expand On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms, Wind Surf renovation now brings you some of the most beautiful public spaces at sea. Collapse |
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Special Sale: Travel Is Better When You're All-In (view details)
14-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: Complimentary All-Inclusive Package on sailings through March 2026 Booking Window: Now - 11/15/25 Applicable Sailings: All sailings through 3/31/26 Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) for voyages through March 31, 2026. All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made. This offer cannot be applied retroactively. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer expires on November 15, 2025. Ships’ registry: Bahamas.
14-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: All-Inclusive Package + Up to $200 Onboard Credit per stateroom + Save 5% when you pay in full Booking Window: Now - 10/31/25 Applicable Sailings: Star Breeze and Wind Star 2027 Tahiti voyages. Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages. Terms & Conditions: For Windstar’s newly released Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for 2026/2027 Caribbean and Latin America voyages. Ships’ registry: Bahamas. For Windstar’s newly released Star Breeze and Wind Star 2027 Tahiti voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Consult your Windstar representative for promotional offer or discount combinability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for Tahiti Star Breeze and Wind Star voyages. Ships’ registry: Bahamas.
14-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: Up to $1,000 Onboard Credit per stateroom on sailings through March 2026 Offer Details:
Booking Window: Now - 10/7/25 Applicable Sailings: All sailings through March 2026 Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) and up to $1,000 Onboard Credit per suite ($500 per guest) for all sailings through March 31, 2026. |
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7-Night Caribbean (Caribbean - All) |
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Ports of Call: Bridgetown, Grande Anse, Castries, Pigeon Island (2 Days), Admiralty Bay, Bequia, Mayreau, St. George's, Bridgetown
Departs: Sun. 1/18/26
Returns: Sun. 1/25/26
Nights: 7
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On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all...
Expand On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms, Wind Surf renovation now brings you some of the most beautiful public spaces at sea. Collapse |
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Special Sale: Travel Is Better When You're All-In (view details)
7-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: Complimentary All-Inclusive Package on sailings through March 2026 Booking Window: Now - 11/15/25 Applicable Sailings: All sailings through 3/31/26 Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) for voyages through March 31, 2026. All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made. This offer cannot be applied retroactively. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer expires on November 15, 2025. Ships’ registry: Bahamas.
7-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: $300 Shipboard Credit per couple on select sailings Booking Window: Now - 12/31/25 Terms & Conditions: Single occupancy bookings receive half the listed shipboard credit.
7-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: All-Inclusive Package + Up to $200 Onboard Credit per stateroom + Save 5% when you pay in full Booking Window: Now - 10/31/25 Applicable Sailings: Star Breeze and Wind Star 2027 Tahiti voyages. Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages. Terms & Conditions: For Windstar’s newly released Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for 2026/2027 Caribbean and Latin America voyages. Ships’ registry: Bahamas. For Windstar’s newly released Star Breeze and Wind Star 2027 Tahiti voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Consult your Windstar representative for promotional offer or discount combinability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for Tahiti Star Breeze and Wind Star voyages. Ships’ registry: Bahamas.
7-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: Up to $1,000 Onboard Credit per stateroom on sailings through March 2026 Offer Details:
Booking Window: Now - 10/7/25 Applicable Sailings: All sailings through March 2026 Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) and up to $1,000 Onboard Credit per suite ($500 per guest) for all sailings through March 31, 2026. |
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14-Night Caribbean (Caribbean - All) |
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Ports of Call: Bridgetown, Grande Anse, Castries, Pigeon Island (2 Days), Admiralty Bay, Bequia, Mayreau, St. George's, Bridgetown, Man-O-War, Tobago, Mayreau, Soufriere Bay, Kralendijk, Bonaire, Willemstad, Oranjestad
Departs: Sun. 1/18/26
Returns: Sun. 2/1/26
Nights: 14
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On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all...
Expand On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms, Wind Surf renovation now brings you some of the most beautiful public spaces at sea. Collapse |
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Special Sale: Travel Is Better When You're All-In (view details)
14-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: Complimentary All-Inclusive Package on sailings through March 2026 Booking Window: Now - 11/15/25 Applicable Sailings: All sailings through 3/31/26 Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) for voyages through March 31, 2026. All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made. This offer cannot be applied retroactively. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer expires on November 15, 2025. Ships’ registry: Bahamas.
14-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: $300 Shipboard Credit per couple on select sailings Booking Window: Now - 12/31/25 Terms & Conditions: Single occupancy bookings receive half the listed shipboard credit.
14-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: All-Inclusive Package + Up to $200 Onboard Credit per stateroom + Save 5% when you pay in full Booking Window: Now - 10/31/25 Applicable Sailings: Star Breeze and Wind Star 2027 Tahiti voyages. Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages. Terms & Conditions: For Windstar’s newly released Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for 2026/2027 Caribbean and Latin America voyages. Ships’ registry: Bahamas. For Windstar’s newly released Star Breeze and Wind Star 2027 Tahiti voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Consult your Windstar representative for promotional offer or discount combinability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for Tahiti Star Breeze and Wind Star voyages. Ships’ registry: Bahamas.
14-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: Up to $1,000 Onboard Credit per stateroom on sailings through March 2026 Offer Details:
Booking Window: Now - 10/7/25 Applicable Sailings: All sailings through March 2026 Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) and up to $1,000 Onboard Credit per suite ($500 per guest) for all sailings through March 31, 2026. |
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7-Night Caribbean (Caribbean - All) |
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Ports of Call: Philipsburg, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Road Bay, Anguilla, Falmouth, Philipsburg
Departs: Sat. 1/24/26
Returns: Sat. 1/31/26
Nights: 7
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On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all...
Expand On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms, Wind Surf renovation now brings you some of the most beautiful public spaces at sea. Collapse |
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| Additional Sailing Dates | |||||||
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7-Night Caribbean (Caribbean - All) |
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Ports of Call: Bridgetown, Man-O-War, Tobago, Mayreau, Soufriere Bay, Kralendijk, Bonaire, Willemstad, Oranjestad
Departs: Sun. 1/25/26
Returns: Sun. 2/1/26
Nights: 7
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On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all...
Expand On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms, Wind Surf renovation now brings you some of the most beautiful public spaces at sea. Collapse |
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Special Sale: Travel Is Better When You're All-In (view details)
7-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: Complimentary All-Inclusive Package on sailings through March 2026 Booking Window: Now - 11/15/25 Applicable Sailings: All sailings through 3/31/26 Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) for voyages through March 31, 2026. All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made. This offer cannot be applied retroactively. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer expires on November 15, 2025. Ships’ registry: Bahamas.
7-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: All-Inclusive Package + Up to $200 Onboard Credit per stateroom + Save 5% when you pay in full Booking Window: Now - 10/31/25 Applicable Sailings: Star Breeze and Wind Star 2027 Tahiti voyages. Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages. Terms & Conditions: For Windstar’s newly released Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for 2026/2027 Caribbean and Latin America voyages. Ships’ registry: Bahamas. For Windstar’s newly released Star Breeze and Wind Star 2027 Tahiti voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Consult your Windstar representative for promotional offer or discount combinability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for Tahiti Star Breeze and Wind Star voyages. Ships’ registry: Bahamas.
7-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: Up to $1,000 Onboard Credit per stateroom on sailings through March 2026 Offer Details:
Booking Window: Now - 10/7/25 Applicable Sailings: All sailings through March 2026 Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) and up to $1,000 Onboard Credit per suite ($500 per guest) for all sailings through March 31, 2026. |
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15-Night Caribbean (Caribbean - All) |
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Ports of Call: Bridgetown, Man-O-War, Tobago, Mayreau, Soufriere Bay, Kralendijk, Bonaire, Willemstad, Oranjestad, Santa Marta, Cartagena, Bocas Del Toro, Colon (2 Days)
Departs: Sun. 1/25/26
Returns: Mon. 2/9/26
Nights: 15
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On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all...
Expand On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms, Wind Surf renovation now brings you some of the most beautiful public spaces at sea. Collapse |
|
|
Special Sale: Travel Is Better When You're All-In (view details)
15-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: Complimentary All-Inclusive Package on sailings through March 2026 Booking Window: Now - 11/15/25 Applicable Sailings: All sailings through 3/31/26 Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) for voyages through March 31, 2026. All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made. This offer cannot be applied retroactively. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer expires on November 15, 2025. Ships’ registry: Bahamas.
15-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: All-Inclusive Package + Up to $200 Onboard Credit per stateroom + Save 5% when you pay in full Booking Window: Now - 10/31/25 Applicable Sailings: Star Breeze and Wind Star 2027 Tahiti voyages. Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages. Terms & Conditions: For Windstar’s newly released Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for 2026/2027 Caribbean and Latin America voyages. Ships’ registry: Bahamas. For Windstar’s newly released Star Breeze and Wind Star 2027 Tahiti voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Consult your Windstar representative for promotional offer or discount combinability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for Tahiti Star Breeze and Wind Star voyages. Ships’ registry: Bahamas.
15-Night Caribbean (Caribbean - All)Wind Surf Windstar Cruises Offer: Up to $1,000 Onboard Credit per stateroom on sailings through March 2026 Offer Details:
Booking Window: Now - 10/7/25 Applicable Sailings: All sailings through March 2026 Terms & Conditions: Windstar is offering a complimentary All-Inclusive package (valued at $99 per guest per day) and up to $1,000 Onboard Credit per suite ($500 per guest) for all sailings through March 31, 2026. |
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