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49 Results

Taxes and fees included in all prices shown

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Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

22-night Star Collector Cruise: Caribbean Beats & Transatlantic Treats From Malaga, Spain

Malaga
Tangier
Casablanca
Funchal (Madeira)
Bridgetown (Barbados)
+8 more

Aboard

Star Legend

From

Malaga, Spain

1 Sailing

Nov 12, 2026

1 Sailing

Nov 12, 2026

Published prices from

$7,458

per person*

taxes & fees included

A stunning panoramic view of Rodney Bay on the island of St. Lucia, showing a bustling harbor filled with sailboats, a colorful town, and lush green hills under a bright blue, cloudy sky.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Seabourn logo

15-night Southern Caribbean In Depth Cruise From Miami, Florida

Miami
San Juan
Jost Van Dyke
Carambola Beach
Roseau
+8 more

Aboard

Seabourn Ovation

From

Miami, Florida

1 Sailing

Nov 20, 2026

1 Sailing

Nov 20, 2026

Published prices from

$7,399

per person*

taxes & fees included

A view of Pigeon Island National Landmark, St. Lucia, showing a lush, green peninsula jutting out into the ocean with waves crashing on the rocks.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

15-night Star Collector: Captivating Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Anse Mitan
Pigeon Island
Castries
The Pitons
+9 more

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Nov 27, 2026

1 Sailing

Nov 27, 2026

Published prices from

$4,768

per person*

taxes & fees included

A breathtaking aerial view of the iconic Pitons, two majestic volcanic peaks, rising from the turquoise waters of the Caribbean Sea on the island of St. Lucia, with a small bay and sailboats.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

16-night Star Collector: Windward Islands & Spanish New World Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Rodney Bay
The Pitons
Scarborough
Bequia
+10 more

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Dec 4, 2026

1 Sailing

Dec 4, 2026

Published prices from

$5,244

per person*

taxes & fees included

A breathtaking tropical beach on Mayreau Island, Grenadines, with white sand, tall palm trees, and turquoise water under a perfectly blue sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

8-night Windward Ways & Tobago Cays Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Rodney Bay
The Pitons
Scarborough
Bequia
+5 more

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Dec 4, 2026

1 Sailing

Dec 4, 2026

Published prices from

$2,760

per person*

taxes & fees included

An aerial view of the colorful waterfront of St. George's, Grenada, with the town's buildings nestled on a hillside and a long, rocky breakwater extending into the calm, turquoise water.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Seabourn logo

14-night Yachtsman's Caribbean In Depth Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)
Sopers Hole
Carambola Beach
Trois Isles
Port Elizabeth (Bequia)
+7 more

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 5, 2026

1 Sailing

Dec 5, 2026

Published prices from

$5,899

per person*

taxes & fees included

A beautiful panoramic view of Roseau, Dominica, with a colorful town nestled between the deep blue Caribbean Sea and a backdrop of lush green, volcanic mountains.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Seabourn logo

7-night Caribbean Gems Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Carambola Beach
Terre-de-Haut
St. Pierre
Roseau
+2 more

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

2 Sailings

Dec 12, 2026 - Feb 6, 2027

2 Sailings

Dec 12, 2026 - Feb 6, 2027

Published prices from

$3,599

per person*

taxes & fees included

An aerial view of Carambola Beach Resort in St. Croix, with red-roofed buildings nestled among lush green tropical trees along the turquoise Caribbean Sea.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Seabourn logo

16-night Leeward Island Holiday Cruise From Miami, Florida

Miami
San Juan
Road Bay
Carambola Beach
Marigot
+8 more

Aboard

Seabourn Quest

From

Miami, Florida

1 Sailing

Dec 20, 2026

1 Sailing

Dec 20, 2026

Published prices from

$10,999

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Seabourn logo

7-night Treasures Of Aruba, Bonaire & Curacao Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Rodney Bay
Willemstad
Oranjestad
Kralendijk

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

1 Sailing

Jan 2, 2027

1 Sailing

Jan 2, 2027

Published prices from

$3,799

per person*

taxes & fees included

A breathtaking aerial view of the iconic Pitons, two majestic volcanic peaks, rising from the turquoise waters of the Caribbean Sea on the island of St. Lucia, with a small bay and sailboats.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

14-night Star Collector: Windward Islands & Spanish New World Cruise From Fuerte Amador, Panama

Fuerte Amador (Panama City)
Panama Canal
Bocas del Toro
San Blas Islands
Cartagena (Colombia)
+10 more

Aboard

Star Legend

From

Fuerte Amador, Panama

1 Sailing

Feb 16, 2027

1 Sailing

Feb 16, 2027

Published prices from

$9,382

per person*

taxes & fees included

A stunning panoramic view of Rodney Bay on the island of St. Lucia, showing a bustling harbor filled with sailboats, a colorful town, and lush green hills under a bright blue, cloudy sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

8-night Windward Ways & Tobago Cays Cruise From Oranjestad, Aruba, Caribbean

Oranjestad
Willemstad
Kralendijk
St. Georges
Rodney Bay
+5 more

Aboard

Star Legend

From

Oranjestad, Aruba, Caribbean

1 Sailing

Feb 22, 2027

1 Sailing

Feb 22, 2027

Published prices from

$4,640

per person*

taxes & fees included

A rugged, high-angle shot of the dramatic rocky coastline of Hebron, Labrador, with waves crashing against the jagged cliffs and dark blue water stretching to the horizon.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

69-night Northern Hemisphere Explorer: Arctic To South America Cruise From Reykjavik, Iceland

Reykjavik
Kangerlussuaq Fjord
Pond Inlet
Northwest Passage
Ellesmere Island
+38 more

Aboard

Seabourn Venture

From

Reykjavik, Iceland

1 Sailing

Aug 17, 2027

1 Sailing

Aug 17, 2027

"A beautiful aerial view of the colorful, snow-covered houses of the small village of Uummannaq, Northwest Greenland, at the foot of the magnificent Uummannaq Mountain. "
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

53-night Arctic Expeditions & Southern Caribbean Harbors Cruise From Reykjavik, Iceland

Reykjavik
Kangerlussuaq Fjord
Pond Inlet
Northwest Passage
Ellesmere Island
+29 more

Aboard

Seabourn Venture

From

Reykjavik, Iceland

1 Sailing

Aug 17, 2027

1 Sailing

Aug 17, 2027

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

94-night Grand Expedition: Pole To Pole Cruise From Reykjavik, Iceland

Reykjavik
Kangerlussuaq Fjord
Pond Inlet
Northwest Passage
Ellesmere Island
+45 more

Aboard

Seabourn Venture

From

Reykjavik, Iceland

1 Sailing

Aug 17, 2027

1 Sailing

Aug 17, 2027

Colorful houses along the waterfront in Nuuk, Greenland.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

82-night Grand Expedition: Arctic To Antarctica Cruise From Reykjavik, Iceland

Reykjavik
Kangerlussuaq Fjord
Nuuk
Iqaluit (Nunavut)
Diana Island
+42 more

Aboard

Seabourn Venture

From

Reykjavik, Iceland

2 Sailings

Aug 29, 2027 - Aug 30, 2028

2 Sailings

Aug 29, 2027 - Aug 30, 2028

A stunning sunset view of a historic stone lighthouse on Rose Island in Newfoundland and Labrador, with its light glowing as the sun sets over the Atlantic Ocean.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

57-night Northern Hemisphere Explorer: Greenland To Brazil Cruise From Reykjavik, Iceland

Reykjavik
Kangerlussuaq Fjord
Nuuk
Iqaluit (Nunavut)
Diana Island
+35 more

Aboard

Seabourn Venture

From

Reykjavik, Iceland

1 Sailing

Aug 29, 2027

1 Sailing

Aug 29, 2027

A vibrant display of the green Northern Lights, or Aurora Borealis, illuminating the dark blue sky over a snow-capped mountain and calm water on Resolution Island.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

41-night Northwest Passage, Labrador Coast & Caribbean Cruise From Reykjavik, Iceland

Reykjavik
Kangerlussuaq Fjord
Nuuk
Iqaluit (Nunavut)
Diana Island
+26 more

Aboard

Seabourn Venture

From

Reykjavik, Iceland

1 Sailing

Aug 29, 2027

1 Sailing

Aug 29, 2027

An aerial view of Carambola Beach Resort in St. Croix, with red-roofed buildings nestled among lush green tropical trees along the turquoise Caribbean Sea.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Seabourn logo

23-night Wild Labrador Coast & Southern Caribbean Cruise From Reykjavik, Iceland

Reykjavik
Kangerlussuaq Fjord
Nuuk
Pangnirtung
Kekerten Island
+18 more

Aboard

Seabourn Venture

From

Reykjavik, Iceland

1 Sailing

Sep 16, 2027

1 Sailing

Sep 16, 2027

A vibrant display of the green Northern Lights, or Aurora Borealis, illuminating the dark blue sky over a snow-capped mountain and calm water on Resolution Island.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

64-night Labrador Coast, Caribbean, South America & Scotia Arc Cruise From Reykjavik, Iceland

Reykjavik
Kangerlussuaq Fjord
Nuuk
Pangnirtung
Kekerten Island
+34 more

Aboard

Seabourn Venture

From

Reykjavik, Iceland

1 Sailing

Sep 16, 2027

1 Sailing

Sep 16, 2027

A beautiful coastal scene in Indian Harbour, Newfoundland, with a wooden boardwalk hugging the rocky shoreline, leading into a dense forest with hints of autumn foliage.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

39-night Wild Labrador Coast, Caribbean & South American Cruise From Reykjavik, Iceland

Reykjavik
Kangerlussuaq Fjord
Nuuk
Pangnirtung
Kekerten Island
+27 more

Aboard

Seabourn Venture

From

Reykjavik, Iceland

1 Sailing

Sep 16, 2027

1 Sailing

Sep 16, 2027

Historic Halifax waterfront buildings.
Up to $2,500 Onboard Credit*
Seabourn logo

8-night Southern Caribbean Yacht Harbors Cruise From Halifax, Nova Scotia

Halifax (Nova Scotia)
Carambola Beach
Little Bay
Rodney Bay
Bridgetown (Barbados)

Aboard

Seabourn Venture

From

Halifax, Nova Scotia

1 Sailing

Oct 1, 2027

1 Sailing

Oct 1, 2027

Published prices from

$4,799

per person*

taxes & fees included

A breathtaking action shot of a killer whale breaching from the deep blue Antarctic waters, with a massive glacier and icebergs in the background.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

49-night Caribbean, South America & Scotia Arc Expedition Cruise From Halifax, Nova Scotia

Halifax (Nova Scotia)
Carambola Beach
Little Bay
Rodney Bay
Bridgetown (Barbados)
+18 more

Aboard

Seabourn Venture

From

Halifax, Nova Scotia

1 Sailing

Oct 1, 2027

1 Sailing

Oct 1, 2027

Rio de Janeiro panoramic with Sugarloaf Mountain and Guanabara Bay.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

24-night Southern Caribbean & South American Expedition Cruise From Halifax, Nova Scotia

Halifax (Nova Scotia)
Carambola Beach
Little Bay
Rodney Bay
Bridgetown (Barbados)
+10 more

Aboard

Seabourn Venture

From

Halifax, Nova Scotia

1 Sailing

Oct 1, 2027

1 Sailing

Oct 1, 2027

Published prices from

$13,899

per person*

taxes & fees included

A sunny view of the colorful waterfront of Willemstad, Curacao, with its iconic pastel-colored Dutch colonial buildings lining the Handelskade street and a ship docked in the port.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

7-night Yacht Harbors Of Bonaire & Curacao Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Rodney Bay
Scarborough
Willemstad
Kralendijk

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

1 Sailing

Dec 11, 2027

1 Sailing

Dec 11, 2027

Published prices from

$5,099

per person*

taxes & fees included

An aerial view of the colorful waterfront of St. John's, Antigua, with a long pier extending into the calm, blue sea and the town's charming buildings and marina in the background.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

17-night Hidden Yacht Harbor Holiday Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Rodney Bay
Scarborough
Willemstad
Kralendijk
+10 more

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

1 Sailing

Dec 11, 2027

1 Sailing

Dec 11, 2027

Published prices from

$11,199

per person*

taxes & fees included

    • Showing results 1 - 24 of 49

*Rates and offers are per person, in US Dollars, based on double occupancy, capacity controlled, subject to availability and confirmation, and may change without notice. Government taxes and fees are included. Rates and offers are available for select dates and categories only. Additional restrictions may apply. Call 1-800-377-9383 for full terms and conditions.