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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, 1/24, 1/25, 2/7, 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, 1/24, 1/25, 2/7, 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_Surf
Cruise Line: Windstar Cruises    Ship: Wind Surf
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
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
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, 1/25, 2/7, 2/28, 3/7, 3/14, 3/21, 3/28, 3/28
Windstar 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: 1/7, 1/31, 2/7, 2/14, 2/21, 2/28, 3/7, 3/14, 3/21
Windstar Cruises
 


14-Night Caribbean (Caribbean - Extended)

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, Charleston, Roseau, Pigeon Island, Pointe a Pitre, Gustavia, Basseterre, Philipsburg
Departs: Sat. 1/31/26     Returns: Sat. 2/14/26     Nights: 14
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: 2/7
Windstar Cruises
 


7-Night Caribbean (Caribbean - All)

Wind_Spirit
Cruise Line: Windstar Cruises    Ship: Wind Spirit
Ports of Call: Philipsburg, St. John's, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg
Departs: Sat. 1/31/26     Returns: Sat. 2/7/26     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: Signature Exclusive Collection Offer (view details)Special Sale: Signature Exclusive Hosted Sailings (view details)Special Sale: Ways to Winter Sales Event (view details)
Additional Sailing Dates
2025 Departures: 12/28
2026 Departures: 1/7, 1/24, 2/7, 2/14, 2/21, 2/28, 3/7, 3/14, 3/21
Windstar Cruises
 


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. 1/31/26     Returns: Sat. 2/7/26     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, 1/17, 1/24, 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
 


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, Basseterre, Trois Ilets, Pointe a Pitre, Roseau, Rodney Bay, Bridgetown
Departs: Sat. 1/31/26     Returns: Sat. 2/14/26     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: 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, 1/24, 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)

SeaDream_I
Cruise Line: SeaDream Yacht Club    Ship: SeaDream I
Ports of Call: Charlotte Amalie, Cruz Bay, Saint John, Prickly Pear Island, Sandy Ground, Gustavia (2 Days), Charlestown, Spanish Town, Virgin Gorda, Norman Island, San Juan
Departs: Sat. 1/3/26     Returns: Sat. 1/10/26     Nights: 7
Named “Best Small Luxury Cruise Ship of 2015” in ForbesLife, twin mega-yachts SeaDream I & II are intimate boutique ships that provide a unique travelling experience unlike any other cruise vacati... expand Expand
Special Sale: Signature Exclusive Collection Offer (view details)
Additional Sailing Dates
2025 Departures: 11/15, 11/22, 11/23, 11/29, 12/6, 12/13, 12/20, 12/27
2026 Departures: 1/31, 2/7, 2/14, 2/21, 2/28, 3/7, 3/14, 3/21, 3/28, 4/4, 4/11, 11/14, 11/21, 11/28, 12/5, 12/12, 12/27
2027 Departures: 1/9, 1/16, 1/23, 1/30, 2/6, 2/13, 2/20, 2/27, 3/6, 3/13, 3/20, 3/27, 4/3, 4/10, 11/7, 11/14, 11/21, 11/28, 12/5, 12/12, 12/27
2028 Departures: 1/9, 1/16, 2/13, 2/20, 2/27, 3/5, 3/12, 3/19, 3/26, 4/8, 4/15
SeaDream Yacht Club
 


7-Night Caribbean (Caribbean - All)

SeaDream_II
Cruise Line: SeaDream Yacht Club    Ship: SeaDream II
Ports of Call: Charlotte Amalie, Spanish Town, Virgin Gorda, Leverick Bay, Virgin Gorda, Prickly Pear Island, Sandy Ground, Philpsburg, Gustavia (2 Days), Cruz Bay, Saint John, Charlotte Amalie
Departs: Sun. 1/4/26     Returns: Sun. 1/11/26     Nights: 7
Named “Best Small Luxury Cruise Ship of 2015” in ForbesLife, twin mega-yachts SeaDream I & II are intimate boutique ships that provide a unique travelling experience unlike any other cruise vacati... expand Expand
Special Sale: Signature Exclusive Collection Offer (view details)
Additional Sailing Dates
2025 Departures: 11/16, 11/30, 12/7, 12/14, 12/21, 12/28
2026 Departures: 1/11, 1/18, 1/25, 2/22, 3/1, 3/8, 3/15, 3/22, 3/29, 4/5, 4/12, 4/19, 12/5, 12/12, 12/27
2027 Departures: 1/3, 1/10, 1/17, 1/24, 1/31, 2/7, 2/14, 2/21, 2/28, 3/13, 3/20, 3/27, 4/3, 11/13, 11/20, 11/27, 12/4, 12/27
2028 Departures: 1/8, 1/15, 1/22, 1/29, 2/5, 3/4, 3/11, 3/18, 3/25, 4/1, 4/8, 4/15
SeaDream Yacht Club
 


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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.