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30 Results

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A vibrant panoramic view of Castries, St. Lucia, with colorful buildings nestled along the harbor and lush green hills in the background under a blue sky with white clouds.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Seabourn logo

14-night Exotic Caribbean In Depth Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Little Bay
St. John's
Carambola Beach
+7 more

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

7 Sailings

Nov 28, 2026 - Mar 13, 2027

7 Sailings

Nov 28, 2026 - Mar 13, 2027

Published prices from

$7,999

per person*

taxes & fees included

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Seabourn logo

7-night Classic Caribbean Yacht Harbors Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Little Bay
St. John's
Carambola Beach
+3 more

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

13 Sailings

Nov 28, 2026 - Mar 11, 2028

13 Sailings

Nov 28, 2026 - Mar 11, 2028

Published prices from

$4,099

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

$3,999

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

$4,099

per person*

taxes & fees included

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

12-night Caribbean & Atlantic Passage Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Funchal (Madeira)
Portimao
Lisbon

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

1 Sailing

Mar 27, 2027

1 Sailing

Mar 27, 2027

Published prices from

$6,389

per person*

taxes & fees included

Rio de Janeiro panoramic with Sugarloaf Mountain and Guanabara Bay.
Seabourn logo

16-night Trinidad To Rio: South American Expedition Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Port of Spain
Devil's Island
Cross Equator
Fortaleza
+6 more

Aboard

Seabourn Venture

From

Bridgetown, Barbados

1 Sailing

Oct 9, 2027

1 Sailing

Oct 9, 2027

Published prices from

$10,599

per person*

taxes & fees included

A prominent circular monument marks the Equator in Uganda, featuring the word "EQUATOR" and "UGANDA" with a grassy landscape in the background.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

41-night South American Expedition To The Scotia Arc Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Port of Spain
Devil's Island
Cross Equator
Fortaleza
+14 more

Aboard

Seabourn Venture

From

Bridgetown, Barbados

1 Sailing

Oct 9, 2027

1 Sailing

Oct 9, 2027

A vibrant panoramic view of Castries, St. Lucia, with colorful buildings nestled along the harbor and lush green hills in the background under a blue sky with white clouds.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

14-night Caribbean Yacht Explorer Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Little Bay
St. John's
Carambola Beach
+7 more

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

6 Sailings

Nov 27, 2027 - Mar 11, 2028

6 Sailings

Nov 27, 2027 - Mar 11, 2028

Published prices from

$8,299

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

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*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

10-night Caribbean Yacht Harbor Holiday Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
St. George's
Port Elizabeth (Bequia)
St. Pierre
Terre-de-Haut
+6 more

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

1 Sailing

Dec 18, 2027

1 Sailing

Dec 18, 2027

Published prices from

$7,299

per person*

taxes & fees included

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

21-night Bonaire, Curacao & Southern Caribbean Holiday Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
St. George's
Port Elizabeth (Bequia)
St. Pierre
Terre-de-Haut
+11 more

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

1 Sailing

Dec 18, 2027

1 Sailing

Dec 18, 2027

Published prices from

$14,299

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 The Abc Islands Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Rodney Bay
Willemstad
Oranjestad
Kralendijk

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

1 Sailing

Jan 8, 2028

1 Sailing

Jan 8, 2028

Published prices from

$5,099

per person*

taxes & fees included

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

14-night Yacht Harbors & Southern Island Discovery Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Rodney Bay
Willemstad
Oranjestad
Kralendijk
+7 more

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

1 Sailing

Jan 8, 2028

1 Sailing

Jan 8, 2028

Published prices from

$8,899

per person*

taxes & fees included

A picturesque view of a narrow, cobblestone street in a historic white-washed village near Motril, Spain, lined with buildings and potted plants.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

21-night Atlantic Crossing From The Caribbean To Spain Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Funchal (Madeira)
Lisbon
Seville (Cadiz)
+8 more

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

1 Sailing

Mar 25, 2028

1 Sailing

Mar 25, 2028

Published prices from

$13,199

per person*

taxes & fees included

Belém Tower on Tagus River.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

12-night Atlantic Crossing Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Funchal (Madeira)
Lisbon

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

2 Sailings

Mar 25, 2028 - Mar 24, 2029

2 Sailings

Mar 25, 2028 - Mar 24, 2029

Published prices from

$6,999

per person*

taxes & fees included

An aerial shot of the port city of Ushuaia, Argentina, at dusk, showing city lights along the Beagle Channel with the snow-capped Andes Mountains in the background.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

41-night South America & Scotia Arc Expedition Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Port of Spain
Devil's Island
Cross Equator
Fortaleza
+13 more

Aboard

Seabourn Venture

From

Bridgetown, Barbados

1 Sailing

Oct 10, 2028

1 Sailing

Oct 10, 2028

A view of the historic town of Paraty, Brazil, with boats docked in the harbor, colonial buildings, and mountains in the distance.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

16-night Exploring Trinidad, French Guiana & Coastal Brazil Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Port of Spain
Devil's Island
Cross Equator
Fortaleza
+6 more

Aboard

Seabourn Venture

From

Bridgetown, Barbados

1 Sailing

Oct 10, 2028

1 Sailing

Oct 10, 2028

Published prices from

$10,999

per person*

taxes & fees included

A vibrant panoramic view of Castries, St. Lucia, with colorful buildings nestled along the harbor and lush green hills in the background under a blue sky with white clouds.
Seabourn logo

14-night Boutique Yacht Harbors Of The Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Port Elizabeth (Bequia)
Trois Isles
St. John's
Carambola Beach
+7 more

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

2 Sailings

Dec 9, 2028 - Jan 20, 2029

2 Sailings

Dec 9, 2028 - Jan 20, 2029

Published prices from

$8,499

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
Seabourn logo

7-night Boutique Yacht Harbors Of The Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Port Elizabeth (Bequia)
Trois Isles
St. John's
Carambola Beach
+3 more

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

3 Sailings

Dec 9, 2028 - Jan 20, 2029

3 Sailings

Dec 9, 2028 - Jan 20, 2029

Published prices from

$4,699

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.
Seabourn logo

14-night Exploring Boutique Yacht Harbors On Holiday Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Port Elizabeth (Bequia)
Trois Isles
St. John's
Carambola Beach
+7 more

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

1 Sailing

Dec 23, 2028

1 Sailing

Dec 23, 2028

Published prices from

$9,899

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
Seabourn logo

7-night Boutique Yacht Harbors Of The Caribbean Holiday Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Port Elizabeth (Bequia)
Trois Isles
St. John's
Carambola Beach
+3 more

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

1 Sailing

Dec 23, 2028

1 Sailing

Dec 23, 2028

Published prices from

$5,499

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
Seabourn logo

14-night Boutique Yacht Harbors & Southern Caribbean Isles Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Port Elizabeth (Bequia)
Trois Isles
St. John's
Carambola Beach
+6 more

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

1 Sailing

Jan 6, 2029

1 Sailing

Jan 6, 2029

Published prices from

$9,399

per person*

taxes & fees included

An aerial view of the vibrant red-roofed houses of Terre-de-Haut in Guadeloupe, with sailboats anchored in the turquoise bay and a small island nearby.
Seabourn logo

21-night Ultimate Caribbean Yacht Harbors Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Rodney Bay
Willemstad
Oranjestad
Kralendijk
+11 more

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

1 Sailing

Feb 3, 2029

1 Sailing

Feb 3, 2029

Published prices from

$14,199

per person*

taxes & fees included

A stunning view of Port Elizabeth in Bequia, St. Vincent and the Grenadines, with a sandy beach lined with palm trees and a building on the shore, and numerous sailboats anchored in the calm turquoise bay.
Seabourn logo

14-night Southern Caribbean Isles & Boutique Yacht Harbors Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Rodney Bay
Willemstad
Oranjestad
Kralendijk
+7 more

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

1 Sailing

Feb 3, 2029

1 Sailing

Feb 3, 2029

Published prices from

$9,399

per person*

taxes & fees included

    • Showing results 1 - 24 of 30

*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.