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112 Results

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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
Azamara logo

14-night Caribbean Voyage: Barbados, St. Lucia & St. Kitts From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Roseau
Basseterre
Charlestown
+9 more

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Nov 14, 2026

1 Sailing

Nov 14, 2026

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Azamara logo

7-night Eastern Caribbean Voyage: St.Lucia, Dominica & St.Kitts From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Roseau
Basseterre
Charlestown
+3 more

Aboard

Azamara Journey

From

Bridgetown, Barbados

2 Sailings

Nov 14 - Nov 28, 2026

2 Sailings

Nov 14 - Nov 28, 2026

Published prices from

$1,069

per person*

taxes & fees included

A scenic view of Catalina Island, Dominican Republic, with a pristine sandy beach lined with palm trees and the calm turquoise waters of the Caribbean Sea in the background.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
MSC Cruises logo

14 nights Dominican Republic From Bridgetown, Barbados

Bridgetown (Barbados)
Fort de France
Pointe A Pitre
Roadtown
La Romana
+5 more

Aboard

MSC Opera

From

Bridgetown, Barbados

23 Sailings

Nov 19, 2026 - Oct 28, 2027

23 Sailings

Nov 19, 2026 - Oct 28, 2027

Published prices from

$1,345

per person*

taxes & fees included

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

18-night Star Collector: Reefs & Rainforests: The Caribbean, Colombia, Panama & Costa Rica Via The Panama Canal Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Bequia
St. George's
Kralendijk
Willemstad
+11 more

Aboard

Wind Star

From

Bridgetown, Barbados

1 Sailing

Nov 24, 2026

1 Sailing

Nov 24, 2026

Published prices from

$8,272

per person*

taxes & fees included

Colorful colonial balconies in Cartagena.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

11-night Colombian & Southern Caribbean Coastlines Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Bequia
St. George's
Kralendijk
Willemstad
+5 more

Aboard

Wind Star

From

Bridgetown, Barbados

1 Sailing

Nov 24, 2026

1 Sailing

Nov 24, 2026

Published prices from

$4,792

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 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
Windstar

7-night Jewels Of The Windward Islands Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Anse Mitan
Pigeon Island
Castries
The Pitons
+3 more

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Nov 27, 2026

1 Sailing

Nov 27, 2026

Published prices from

$2,458

per person*

taxes & fees included

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

14-night Caribbean Voyage: Barbados, St. Lucia & St. Maarten From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Roseau
Basseterre
Charlestown
+9 more

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Nov 28, 2026

1 Sailing

Nov 28, 2026

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

$6,199

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

$3,699

per person*

taxes & fees included

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

13 nights South Caribbean From Bridgetown, Barbados

Bridgetown (Barbados)
St. George's
Fort de France
Pointe A Pitre
St. John's
+5 more

Aboard

MSC World Europa

From

Bridgetown, Barbados

1 Sailing

Dec 2, 2026

1 Sailing

Dec 2, 2026

Published prices from

$1,758

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
MSC Cruises logo

13 nights South Caribbean From Bridgetown, Barbados

Bridgetown (Barbados)
St. George's
Kingston
Fort de France
Pointe A Pitre
+6 more

Aboard

MSC Seaview

From

Bridgetown, Barbados

1 Sailing

Dec 2, 2026

1 Sailing

Dec 2, 2026

Published prices from

$1,692

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

A panoramic view of Fort-de-France, Martinique, showing a bustling bay filled with boats and yachts, with colorful houses nestled on the surrounding green hillsides and the deep blue Caribbean Sea beyond.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

7-night Southern Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Bequia
Fort de France
Deshaies
Gustavia
+2 more

Aboard

Silver Spirit

From

Bridgetown, Barbados

2 Sailings

Dec 5, 2026 - Feb 28, 2027

2 Sailings

Dec 5, 2026 - Feb 28, 2027

Published prices from

$3,950

per person*

taxes & fees included

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

6-night Eastern Caribbean Voyage: St.Lucia, Dominica & St.Kitts From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Roseau
Basseterre
Charlestown
+2 more

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

Published prices from

$669

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*+ 2 more offers
TCW EXCLUSIVE
Azamara logo

16-night Caribbean Christmas Voyage: Barbados, St. Lucia & St. Thomas From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Roseau
Basseterre
Charlestown
+11 more

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

Published prices from

$5,279

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

The picturesque fishing village of Deshaies, Guadeloupe, with its colorful waterfront and red-roofed church nestled on a tranquil bay.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

10-night Southern Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Fort de France
Roseau
St. John's
+2 more

Aboard

Silver Spirit

From

Bridgetown, Barbados

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

Published prices from

$3,950

per person*

taxes & fees included

An aerial view of Kingston Beach, a residential suburb near Hobart, Tasmania, Australia. The image shows the curved white-sand beach and the adjacent neighborhood of houses and streets, bordering the calm, blue waters of the River Derwent estuary.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
MSC Cruises logo

14 nights South Caribbean From Bridgetown, Barbados

Bridgetown (Barbados)
Kingston
St. George's
Fort de France
Pointe A Pitre
+5 more

Aboard

MSC World Europa

From

Bridgetown, Barbados

8 Sailings

Dec 15, 2026 - Mar 23, 2027

8 Sailings

Dec 15, 2026 - Mar 23, 2027

Published prices from

$1,661

per person*

taxes & fees included

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

14 nights South Caribbean From Bridgetown, Barbados

Bridgetown (Barbados)
Kingston
St. George's
Fort de France
Pointe A Pitre
+5 more

Aboard

MSC Seaview

From

Bridgetown, Barbados

8 Sailings

Dec 15, 2026 - Mar 23, 2027

8 Sailings

Dec 15, 2026 - Mar 23, 2027

Published prices from

$1,470

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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

8-night Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Bequia
Canouan Island
Roseau
Anguilla
+3 more

Aboard

Silver Spirit

From

Bridgetown, Barbados

2 Sailings

Dec 19 - Dec 27, 2026

2 Sailings

Dec 19 - Dec 27, 2026

Published prices from

$5,050

per person*

taxes & fees included

A scenic landscape view of Admiralty Bay in Bequia, St. Vincent and the Grenadines, with dozens of sailboats moored on the vibrant turquoise water, surrounded by lush green hills.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

8-night Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Soufriere
Bequia
St. George's
Fort de France
+4 more

Aboard

Silver Nova

From

Bridgetown, Barbados

1 Sailing

Dec 21, 2026

1 Sailing

Dec 21, 2026

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
Azamara logo

8-night Caribbean Voyage: Curacao, Aruba & St.Lucia From Bridgetown, Barbados

Bridgetown (Barbados)
Oranjestad
Willemstad
Castries
Charlestown
+3 more

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Dec 28, 2026

1 Sailing

Dec 28, 2026

Published prices from

$2,189

per person*

taxes & fees included

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

17-night Caribbean New Year Voyage: Barbados, Aruba & St. Barts From Bridgetown, Barbados

Bridgetown (Barbados)
Oranjestad
Willemstad
Castries
Charlestown
+10 more

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Dec 28, 2026

1 Sailing

Dec 28, 2026

Published prices from

$5,419

per person*

taxes & fees included

    • Showing results 1 - 24 of 112

*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.