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14-Night Caribbean (Caribbean - All)

Seabourn_Ovation
Cruise Line: Seabourn    Ship: Seabourn Ovation
Ports of Call: Bridgetown, Castries, Little Bay, St. John's, Basseterre, Great Harbour, Jost Van Dyke BVI, Philipsburg, Tortola, Basseterre, Miquelon Island, Port Elizabeth, Bequia, St. Georges, Bridgetown
Departs: Sat. 1/24/26     Returns: Sat. 2/7/26     Nights: 14
Last year, Seabourn introduced Seabourn Ovation, a sister-ship to the already prestigious Seabourn Encore. Seabourn Ovation represents another welcome stage in the evolution of small-ship cruising, wh... expand Expand
Special Sale: Post Cruise Offer (view details)Special Sale: Cruise Planners Exclusive - $250 Onboard Credit on Select Sailings - Amenity Tracker Submission Required (view details)Special Sale: Signature Exclusive Collection Offer (view details)Special Sale: Signature Exclusive Private Car & Guide Tour (view details)Special Sale: More Moments on Us (view details)Special Sale: Signature Partner of the Month - Up to $300 Onboard Credit (view details)
Additional Sailing Dates
2026 Departures: 1/3, 1/10, 1/17, 1/31, 2/7, 2/14, 2/21, 2/28, 3/7, 3/21, 11/21, 11/28, 12/5, 12/19
2027 Departures: 1/9, 1/16, 1/19, 1/23, 2/13, 2/20, 2/27, 3/6, 3/13
Seabourn
 


7-Night Caribbean (Caribbean - All)

Seabourn_Ovation
Cruise Line: Seabourn    Ship: Seabourn Ovation
Ports of Call: Bridgetown, Castries, Little Bay, St. John's, Basseterre, Great Harbour, Jost Van Dyke BVI, Philipsburg
Departs: Sat. 1/24/26     Returns: Sat. 1/31/26     Nights: 7
Last year, Seabourn introduced Seabourn Ovation, a sister-ship to the already prestigious Seabourn Encore. Seabourn Ovation represents another welcome stage in the evolution of small-ship cruising, wh... expand Expand
Special Sale: Signature Exclusive Collection Offer (view details)Special Sale: Signature Exclusive Hosted Sailings (view details)Special Sale: Signature Exclusive Private Car & Guide Tour (view details)Special Sale: More Moments on Us (view details)Special Sale: Signature Partner of the Month - Up to $300 Onboard Credit (view details)
Additional Sailing Dates
2026 Departures: 1/3, 1/10, 1/17, 1/31, 2/7, 2/14, 2/21, 2/28, 3/7, 3/14, 3/21, 3/28, 11/21, 11/28, 12/5, 12/12, 12/19, 12/26
2027 Departures: 1/2, 1/9, 1/16, 1/23, 1/30, 2/6, 2/13, 2/20, 2/27, 3/6, 3/13, 3/20
Seabourn
 


9-Night Caribbean (Caribbean - All)

Silver_Shadow
Cruise Line: Silversea Cruises    Ship: Silver Shadow
Ports of Call: Bridgetown, Soufriere Bay, Admiralty Bay, Bequia, Kralendijk, Bonaire, Willemstad, Oranjestad (2 Days), Santa Marta, Cartagena
Departs: Sun. 1/25/26     Returns: Tue. 2/3/26     Nights: 9
Award-winning Silver Shadow has all the hallmarks of extreme luxury at sea. With one of the highest space-to-guest ratios at sea, Silver Shadow is a firm favourite in the Silversea fleet. Authentic e... expand Expand
Special Sale: Signature Exclusive Collection Offer (view details)Special Sale: Signature Exclusive Hosted Sailings (view details)Special Sale: Save up to 40% on select sailings (view details)
Additional Sailing Dates
2025 Departures: 11/22, 12/1, 12/10, 12/19
2026 Departures: 2/3, 3/5, 3/14
Silversea Cruises
 


15-Night Caribbean (Caribbean - All)

Wind_Surf
Cruise Line: Windstar Cruises    Ship: Wind Surf
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
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 Expand
Special Sale: Travel Is Better When You're All-In (view details)Special Sale: Early Booking Offer - Tropics 2026/2027 & Tahiti 2027 (view details)Special Sale: Ways to Winter Sales Event (view details)
 
Windstar Cruises
 


7-Night Caribbean (Caribbean - All)

Wind_Surf
Cruise Line: Windstar Cruises    Ship: Wind Surf
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
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 Expand
Special Sale: Travel Is Better When You're All-In (view details)Special Sale: Early Booking Offer - Tropics 2026/2027 & Tahiti 2027 (view details)Special Sale: Ways to Winter Sales Event (view details)
Additional Sailing Dates
2025 Departures: 12/7, 12/14, 12/14, 12/21, 12/28, 12/28
2026 Departures: 1/4, 1/4, 1/11, 1/18, 2/28, 3/7, 3/14, 3/21, 3/28, 3/28
Windstar Cruises
 


7-Night Caribbean (Caribbean - All)

Silver_Spirit
Cruise Line: Silversea Cruises    Ship: Silver Spirit
Ports of Call: Bridgetown, Castries, Fort de France, Gustavia, Roseau, St. George's, Admiralty Bay, Bequia, Bridgetown
Departs: Mon. 1/26/26     Returns: Mon. 2/2/26     Nights: 7
The all-new Silver Spirit has never looked better, nor felt cosier. Fully refurbished for a superlative onboard adventure, she retains our world famous standards of service and home away from home fee... expand Expand
Special Sale: Signature Exclusive Collection Offer (view details)Special Sale: Save up to 40% on select sailings (view details)
Additional Sailing Dates
2025 Departures: 12/8, 12/15, 12/22, 12/29
2026 Departures: 2/2, 2/23, 12/5, 12/12
2027 Departures: 2/28
Silversea Cruises
 


19-Night Caribbean (Caribbean - All)

Insignia
Cruise Line: Oceania Cruises    Ship: Insignia
Ports of Call: Bridgetown, Amazon River, Santarem, Parintins, Manaus (2 Days), Boca de Valeria, Alter do Chao, Amazon River, Devil's Island, Buccoo Reef (Scarborough), Port of Spain, St. George's, Kingstown, Castries, Bridgetown
Departs: Tue. 1/27/26     Returns: Sun. 2/15/26     Nights: 19
The acclaimed Insignia has undergone a multimillion-dollar transformation to create a virtually new ship that is both sleek and elegantly charming. Her decks are resplendent in the finest teak, custom... expand Expand
Special Sale: Your World Included (view details)Special Sale: Cruise Planners Exclusive - Up to $1,000 Shipboard Credit (view details)
 
Oceania Cruises
 


7-Night Caribbean (Caribbean - All)

Royal_Clipper
Cruise Line: Star Clippers    Ship: Royal Clipper
Ports of Call: Bridgetown, Captain's Best, Saint George's, Tobago Cays + Carriacou, Bequia, Kingstown, Martinique/Fort-de-France, French West Indies, Martinique, Soufriere, Marigot Bay, Bridgetown
Departs: Sat. 1/31/26     Returns: Sat. 2/7/26     Nights: 7
Influenced by the German tall ship Preussen, which graced the seas for eight years before it was involved in an accident in 1910, the Royal Clipper has the proud distinction of being the largest and o... expand Expand
Special Sale: Signature Exclusive Collection Offer (view details)
Additional Sailing Dates
2025 Departures: 11/29, 12/6, 12/20
2026 Departures: 1/3, 1/10, 1/17, 2/14, 2/28, 3/14, 11/28, 12/12, 12/26
2027 Departures: 1/9, 1/23, 2/6, 2/20, 3/6, 3/20
Star Clippers
 


7-Night Caribbean (Caribbean - All)

Silver_Shadow
Cruise Line: Silversea Cruises    Ship: Silver Shadow
Ports of Call: Philipsburg, St. John's, St. Thomas, Little Bay, Castries, Mayreau, Pointe a Pitre, Philipsburg
Departs: Sun. 1/4/26     Returns: Sun. 1/11/26     Nights: 7
Award-winning Silver Shadow has all the hallmarks of extreme luxury at sea. With one of the highest space-to-guest ratios at sea, Silver Shadow is a firm favourite in the Silversea fleet. Authentic e... expand Expand
Special Sale: Signature Exclusive Collection Offer (view details)Special Sale: Save up to 40% on select sailings (view details)
Additional Sailing Dates
2025 Departures: 12/28
2026 Departures: 1/11, 1/18, 2/12, 2/19, 2/26, 12/20, 12/27
2027 Departures: 1/3, 1/30, 2/26
Silversea Cruises
 


7-Night Caribbean (Caribbean - All)

Wind_Surf
Cruise Line: Windstar Cruises    Ship: Wind Surf
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
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 Expand
Special Sale: Travel Is Better When You're All-In (view details)Special Sale: Early Booking Offer - Tropics 2026/2027 & Tahiti 2027 (view details)Special Sale: Ways to Winter Sales Event (view details)
Additional Sailing Dates
2025 Departures: 12/7, 12/14, 12/14, 12/21, 12/28, 12/28
2026 Departures: 1/4, 1/11, 1/18, 1/25, 2/28, 3/7, 3/14, 3/21, 3/28, 3/28
Windstar Cruises
 


14-Night Caribbean (Caribbean - All)

Wind_Surf
Cruise Line: Windstar Cruises    Ship: Wind Surf
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
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 Expand
Special Sale: Travel Is Better When You're All-In (view details)Special Sale: Early Booking Offer - Tropics 2026/2027 & Tahiti 2027 (view details)Special Sale: Ways to Winter Sales Event (view details)
Additional Sailing Dates
2025 Departures: 12/14
2026 Departures: 1/11, 1/18
Windstar Cruises
 


22-Night Caribbean (Caribbean - Extended)

Wind_Surf
Cruise Line: Windstar Cruises    Ship: Wind Surf
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
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 Expand
Special Sale: Travel Is Better When You're All-In (view details)Special Sale: Early Booking Offer - Tropics 2026/2027 & Tahiti 2027 (view details)Special Sale: Ways to Winter Sales Event (view details)
 
Windstar Cruises
 


55-Night Caribbean (Caribbean - Extended)

Wind_Surf
Cruise Line: Windstar Cruises    Ship: Wind Surf
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
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 Expand
Special Sale: Travel Is Better When You're All-In (view details)Special Sale: Early Booking Offer - Tropics 2026/2027 & Tahiti 2027 (view details)Special Sale: Ways to Winter Sales Event (view details)
 
Windstar Cruises
 


28-Night Caribbean (Caribbean - All)

Wind_Surf
Cruise Line: Windstar Cruises    Ship: Wind Surf
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
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 Expand
Special Sale: Travel Is Better When You're All-In (view details)Special Sale: Early Booking Offer - Tropics 2026/2027 & Tahiti 2027 (view details)Special Sale: Ways to Winter Sales Event (view details)
 
Windstar Cruises
 


7-Night Caribbean (Caribbean - All)

Silver_Shadow
Cruise Line: Silversea Cruises    Ship: Silver Shadow
Ports of Call: Philipsburg, St. John's, St. Thomas, Little Bay, Castries, Mayreau, Pointe a Pitre, Philipsburg
Departs: Sun. 1/11/26     Returns: Sun. 1/18/26     Nights: 7
Award-winning Silver Shadow has all the hallmarks of extreme luxury at sea. With one of the highest space-to-guest ratios at sea, Silver Shadow is a firm favourite in the Silversea fleet. Authentic e... expand Expand
Special Sale: Save up to 40% on select sailings (view details)
Additional Sailing Dates
2025 Departures: 12/28
2026 Departures: 1/4, 1/18, 2/12, 2/19, 2/26, 12/20, 12/27
2027 Departures: 1/3, 1/30, 2/26
Silversea Cruises
 


14-Night Caribbean (Caribbean - All)

Silver_Shadow
Cruise Line: Silversea Cruises    Ship: Silver Shadow
Ports of Call: Philipsburg, St. John's, St. Thomas, Little Bay, Castries, Mayreau, Pointe a Pitre, Philipsburg, St. John Island, Gustavia, Roseau, St. George's, Trois Ilets, Port Royal, Bridgetown
Departs: Sun. 1/11/26     Returns: Sun. 1/25/26     Nights: 14
Award-winning Silver Shadow has all the hallmarks of extreme luxury at sea. With one of the highest space-to-guest ratios at sea, Silver Shadow is a firm favourite in the Silversea fleet. Authentic e... expand Expand
Additional Sailing Dates
2026 Departures: 2/19, 12/20
Silversea Cruises
 


7-Night Caribbean (Caribbean - All)

Wind_Surf
Cruise Line: Windstar Cruises    Ship: Wind Surf
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
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 Expand
Special Sale: Travel Is Better When You're All-In (view details)Special Sale: Early Booking Offer - Tropics 2026/2027 & Tahiti 2027 (view details)Special Sale: Ways to Winter Sales Event (view details)
Additional Sailing Dates
2025 Departures: 12/7, 12/14, 12/14, 12/21, 12/28, 12/28
2026 Departures: 1/4, 1/4, 1/18, 1/25, 2/28, 3/7, 3/14, 3/21, 3/28, 3/28
Windstar Cruises
 


14-Night Caribbean (Caribbean - All)

Wind_Surf
Cruise Line: Windstar Cruises    Ship: Wind Surf
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
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 Expand
Special Sale: Travel Is Better When You're All-In (view details)Special Sale: Early Booking Offer - Tropics 2026/2027 & Tahiti 2027 (view details)Special Sale: Ways to Winter Sales Event (view details)
Additional Sailing Dates
2025 Departures: 12/14
2026 Departures: 1/4, 1/18
Windstar Cruises
 


17-Night Caribbean (Caribbean - Extended)

Wind_Spirit
Cruise Line: Windstar Cruises    Ship: Wind Spirit
Ports of Call: Philipsburg, Little Bay, Roseau, Castries, Mayreau, St. George's, Admiralty Bay, Bequia, Grande Anse, Pointe a Pitre, Gustavia, Philipsburg, Tortola, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, Gustavia, Road Bay, Anguilla, Falmouth, Philipsburg
Departs: Wed. 1/14/26     Returns: Sat. 1/31/26     Nights: 17
With wide open, teak decks, the Wind Spirit is truly remarkable for a ship of its size. Plenty of spacious public places mean you can easily socialise with friends or just enjoy a quiet drink. Wind Sp... expand Expand
Special Sale: Travel Is Better When You're All-In (view details)Special Sale: Ways to Winter Sales Event (view details)
 
Windstar Cruises
 


10-Night Caribbean (Caribbean - All)

Wind_Spirit
Cruise Line: Windstar Cruises    Ship: Wind Spirit
Ports of Call: Philipsburg, Basseterre, Roseau, Castries, Grande Anse, Pointe a Pitre, Charleston, Leverick Bay, Virgin Gorda, Great Harbour, Jost Van Dyke BVI, Gustavia, Philipsburg
Departs: Wed. 1/14/26     Returns: Sat. 1/24/26     Nights: 10
With wide open, teak decks, the Wind Spirit is truly remarkable for a ship of its size. Plenty of spacious public places mean you can easily socialise with friends or just enjoy a quiet drink. Wind Sp... expand Expand
Special Sale: Travel Is Better When You're All-In (view details)Special Sale: Ways to Winter Sales Event (view details)
Additional Sailing Dates
2026 Departures: 1/4
Windstar Cruises
 


14-Night Caribbean (Caribbean - All)

Seabourn_Ovation
Cruise Line: Seabourn    Ship: Seabourn Ovation
Ports of Call: Philipsburg, Tortola, Basseterre, Miquelon Island, Port Elizabeth, Bequia, St. Georges, Bridgetown, Castries, Little Bay, St. John's, Basseterre, Great Harbour, Jost Van Dyke BVI, Philipsburg
Departs: Sat. 1/17/26     Returns: Sat. 1/31/26     Nights: 14
Last year, Seabourn introduced Seabourn Ovation, a sister-ship to the already prestigious Seabourn Encore. Seabourn Ovation represents another welcome stage in the evolution of small-ship cruising, wh... expand Expand
Special Sale: Future Cruise Deposit (view details)Special Sale: Post Cruise Offer (view details)Special Sale: Cruise Planners Exclusive - $250 Onboard Credit on Select Sailings - Amenity Tracker Submission Required (view details)Special Sale: Signature Exclusive Collection Offer (view details)Special Sale: Signature Exclusive Private Car & Guide Tour (view details)Special Sale: More Moments on Us (view details)Special Sale: Signature Partner of the Month - Up to $300 Onboard Credit (view details)
Additional Sailing Dates
2026 Departures: 1/3, 1/10, 1/24, 1/31, 2/7, 2/14, 2/21, 2/28, 3/7, 3/21, 11/21, 11/28, 12/5, 12/19
2027 Departures: 1/9, 1/16, 1/19, 1/23, 2/13, 2/20, 2/27, 3/6, 3/13
Seabourn
 


7-Night Caribbean (Caribbean - All)

Seabourn_Ovation
Cruise Line: Seabourn    Ship: Seabourn Ovation
Ports of Call: Philipsburg, Tortola, Basseterre, Miquelon Island, Port Elizabeth, Bequia, St. Georges, Bridgetown
Departs: Sat. 1/17/26     Returns: Sat. 1/24/26     Nights: 7
Last year, Seabourn introduced Seabourn Ovation, a sister-ship to the already prestigious Seabourn Encore. Seabourn Ovation represents another welcome stage in the evolution of small-ship cruising, wh... expand Expand
Special Sale: Future Cruise Deposit (view details)Special Sale: Post Cruise Offer (view details)Special Sale: Cruise Planners Exclusive - $250 Onboard Credit on Select Sailings - Amenity Tracker Submission Required (view details)Special Sale: Signature Exclusive Collection Offer (view details)Special Sale: More Moments on Us (view details)Special Sale: Signature Partner of the Month - Up to $300 Onboard Credit (view details)
Additional Sailing Dates
2026 Departures: 1/3, 1/10, 1/24, 1/31, 2/7, 2/14, 2/21, 2/28, 3/7, 3/14, 3/21, 3/28, 11/21, 11/28, 12/5, 12/12, 12/19, 12/26
2027 Departures: 1/2, 1/9, 1/16, 1/23, 1/30, 2/6, 2/13, 2/20, 2/27, 3/6, 3/13, 3/20
Seabourn
 


7-Night Caribbean (Caribbean - Eastern)

sea_cloud_spirit
Cruise Line: Sea Cloud Cruises    Ship: Sea Cloud Spirit
Ports of Call: Philipsburg, Saint Pierre (Martinique), Soufriere, Cabrits, Charlestown, Road Bay, Philipsburg
Departs: Sun. 1/18/26     Returns: Sun. 1/25/26     Nights: 7
Building a three-mast full-rigged ship with traditional rigging in the 21st century may seem a little unusual. For SEA CLOUD CRUISES it is a commitment to true passion for sailing. With her clear, cla... expand Expand
 
Sea Cloud Cruises
 


7-Night Caribbean (Caribbean - All)

Silver_Shadow
Cruise Line: Silversea Cruises    Ship: Silver Shadow
Ports of Call: Philipsburg, St. John Island, Gustavia, Roseau, St. George's, Trois Ilets, Port Royal, Bridgetown
Departs: Sun. 1/18/26     Returns: Sun. 1/25/26     Nights: 7
Award-winning Silver Shadow has all the hallmarks of extreme luxury at sea. With one of the highest space-to-guest ratios at sea, Silver Shadow is a firm favourite in the Silversea fleet. Authentic e... expand Expand
Special Sale: Signature Exclusive Collection Offer (view details)Special Sale: Save up to 40% on select sailings (view details)
Additional Sailing Dates
2025 Departures: 12/28
2026 Departures: 1/4, 1/11, 2/12, 2/19, 2/26, 12/20, 12/27
2027 Departures: 1/3, 1/30, 2/26
Silversea Cruises
 


7-Night Caribbean (Caribbean - All)

Wind_Spirit
Cruise Line: Windstar Cruises    Ship: Wind Spirit
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
With wide open, teak decks, the Wind Spirit is truly remarkable for a ship of its size. Plenty of spacious public places mean you can easily socialise with friends or just enjoy a quiet drink. Wind Sp... expand Expand
Special Sale: Travel Is Better When You're All-In (view details)Special Sale: Ways to Winter Sales Event (view details)
Additional Sailing Dates
2025 Departures: 12/28
2026 Departures: 1/31, 2/7, 2/14, 2/21, 2/28, 3/21
Windstar Cruises
 


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Prices are per person, double occupancy, cruise only and on select sailings. Prices shown are for stateroom categories as noted and are shown in US Dollars. Government taxes and fees are additional. Airfare is not included. Prices and itineraries are based on availability and are subject to change without notice.