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24 Results

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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
Carnival Cruise Line Logo

14-night Journeys - Southern Caribbean Cruise From Port Canaveral, Florida

Port Canaveral
St. Thomas (Charlotte Amalie)
St. John's
Fort de France
St. George's
+5 more

Aboard

Carnival Venezia

From

Port Canaveral, Florida

1 Sailing

Oct 18, 2026

1 Sailing

Oct 18, 2026

Published prices from

$1,167

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Royal Caribbean logo

7-night Southern Caribbean Cruise From San Juan, Puerto Rico

San Juan
Roadtown
St. John's
Fort de France
St. Vincent (Kingstown)
+2 more

Aboard

Vision of the Seas

From

San Juan, Puerto Rico

42 Sailings

Nov 1, 2026 - Apr 16, 2028

42 Sailings

Nov 1, 2026 - Apr 16, 2028

Published prices from

$493

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*+ 4 more offers
TCW EXCLUSIVE
Celebrity Cruise Line logo

11-night Southern Caribbean Intensive Cruise From San Juan, Puerto Rico

San Juan
Roadtown
St. John's
Castries
St. George's
+5 more

Aboard

Celebrity Constellation

From

San Juan, Puerto Rico

1 Sailing

Nov 17, 2026

1 Sailing

Nov 17, 2026

Boats on a canal in Fort Lauderdale.
Up to $500 FREE Onboard Credit*+ 4 more offers
TCW EXCLUSIVE
Celebrity Cruise Line logo

10-night Best Of Southern Caribbean Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
St. John's
Castries
Bridgetown (Barbados)
St. Vincent (Kingstown)
+2 more

Aboard

Celebrity Eclipse

From

Fort Lauderdale, Florida

2 Sailings

Jan 29 - Mar 12, 2027

2 Sailings

Jan 29 - Mar 12, 2027

Published prices from

$1,561

per person*

taxes & fees included

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

12-night Exotic Caribbean Escape Voyage From Miami, Florida

Miami
Oranjestad
Willemstad
St. Vincent (Kingstown)
Castries
+4 more

Aboard

Marina

From

Miami, Florida

1 Sailing

Feb 1, 2027

1 Sailing

Feb 1, 2027

Published prices from

$3,949

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*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

15-night Cultural Currents Cruise From Miami, Florida

Miami
Roadtown
Gustavia
Fort de France
St. Vincent (Kingstown)
+6 more

Aboard

Seven Seas Mariner

From

Miami, Florida

1 Sailing

Mar 26, 2027

1 Sailing

Mar 26, 2027

Published prices from

$12,799

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Royal Caribbean logo

7-night Colon To San Juan Cruise From Colon, Panama

Colon (Panama)
St. Vincent (Kingstown)
Castries
St. John's
Roadtown
+2 more

Aboard

Grandeur of the Seas

From

Colon, Panama

1 Sailing

Apr 24, 2027

1 Sailing

Apr 24, 2027

Published prices from

$756

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*+ 4 more offers
TCW EXCLUSIVE
Celebrity Cruise Line logo

9-night Southern Caribbean Cruise From San Juan, Puerto Rico

San Juan
St. John's
Castries
St. George's
Bridgetown (Barbados)
+3 more

Aboard

Celebrity Summit

From

San Juan, Puerto Rico

1 Sailing

Oct 29, 2027

1 Sailing

Oct 29, 2027

Published prices from

$817

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*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

14-night Festive Caribbean Frolic Voyage From Miami, Florida

Miami
Oranjestad
Willemstad
Kralendijk
St. George's
+6 more

Aboard

Sirena

From

Miami, Florida

1 Sailing

Dec 22, 2027

1 Sailing

Dec 22, 2027

Published prices from

$4,399

per person*

taxes & fees included

Boats on a canal in Fort Lauderdale.
Up to $500 FREE Onboard Credit*+ 4 more offers
TCW EXCLUSIVE
Celebrity Cruise Line logo

13-night Ultimate Southern Caribbean Holiday Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Oranjestad
Willemstad
Kralendijk
St. Vincent (Kingstown)
+4 more

Aboard

Celebrity Eclipse

From

Fort Lauderdale, Florida

1 Sailing

Dec 23, 2027

1 Sailing

Dec 23, 2027

Published prices from

$2,726

per person*

taxes & fees included

An aerial panoramic view of a winding road overlooking Frigate Bay and the Caribbean Sea, with rolling green hills, a beach, and the town of Basseterre, St. Kitts.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Cunard

26-night Transatlantic Cruise From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
Basseterre
St. Vincent (Kingstown)
Bridgetown (Barbados)
+7 more

Aboard

Queen Elizabeth

From

Miami, Florida

1 Sailing

Dec 23, 2027

1 Sailing

Dec 23, 2027

Published prices from

$3,799

per person*

taxes & fees included

A wide-angle view of the bustling harbor of Charlotte Amalie, St. Thomas, with many sailboats and yachts docked in the tranquil blue water, and the town's buildings climbing the lush green hills.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Royal Caribbean logo

8-night Southern Caribbean Holiday Cruise From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
St. Croix
Basseterre
Castries
+3 more

Aboard

Rhapsody of the Seas

From

San Juan, Puerto Rico

1 Sailing

Dec 31, 2027

1 Sailing

Dec 31, 2027

Published prices from

$1,251

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
Regent Seven Seas Cruises.

10-night Untouched Treasures Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
St. George's
St. Vincent (Kingstown)
Castries
Fort de France
+5 more

Aboard

Seven Seas Grandeur

From

Bridgetown, Barbados

1 Sailing

Jan 15, 2028

1 Sailing

Jan 15, 2028

Published prices from

$8,449

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

10-night Tropical Heart & Soul Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
St. Vincent (Kingstown)
Castries
Fort de France
Pointe A Pitre
+5 more

Aboard

Seven Seas Grandeur

From

Bridgetown, Barbados

1 Sailing

Jan 25, 2028

1 Sailing

Jan 25, 2028

Published prices from

$6,549

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
Regent Seven Seas Cruises.

10-night Be My Island Valentine Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
St. George's
St. Vincent (Kingstown)
Castries
Fort de France
+5 more

Aboard

Seven Seas Grandeur

From

Bridgetown, Barbados

1 Sailing

Feb 14, 2028

1 Sailing

Feb 14, 2028

Published prices from

$6,449

per person*

taxes & fees included

A unique architectural close-up of Casapueblo, a white plaster Mediterranean-style villa and museum built by Carlos Páez Vilaró on the cliffs of Punta del Este, Uruguay, against a clear blue sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Oceania Cruises

71-night Grand South America Adventure Voyage From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
Roadtown
St. Maarten (Philipsburg)
Gustavia
+40 more

Aboard

Oceania Aurelia

From

Miami, Florida

1 Sailing

Oct 27, 2028

1 Sailing

Oct 27, 2028

Published prices from

$37,399

per person*

taxes & fees included

An aerial view of Fortaleza de São Tiago, a historic yellow fortress, on the coastline of Funchal, Madeira, with the densely packed city and green mountains in the background.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Oceania Cruises

14-night Brazilian Coastal Odyssey Voyage From Bridgetown, Barbados

Bridgetown (Barbados)
St. Vincent (Kingstown)
St. George's
Devil's Island
Fortaleza
+5 more

Aboard

Oceania Aurelia

From

Bridgetown, Barbados

1 Sailing

Nov 8, 2028

1 Sailing

Nov 8, 2028

Published prices from

$7,099

per person*

taxes & fees included

An aerial panoramic view of a winding road overlooking Frigate Bay and the Caribbean Sea, with rolling green hills, a beach, and the town of Basseterre, St. Kitts.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

14-night The Spicewind Trail Cruise From Miami, Florida

Miami
Bahamian Waters
Ocho Rios
Oranjestad
Willemstad
+6 more

Aboard

Seven Seas Prestige

From

Miami, Florida

1 Sailing

Nov 25, 2028

1 Sailing

Nov 25, 2028

Published prices from

$9,899

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
Regent Seven Seas Cruises.

12-night Celebrate The Caribbean Cruise From Miami, Florida

Miami
Florida Strait
Oranjestad
Willemstad
Kralendijk
+7 more

Aboard

Seven Seas Grandeur

From

Miami, Florida

1 Sailing

Dec 27, 2028

1 Sailing

Dec 27, 2028

Published prices from

$8,549

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
Regent Seven Seas Cruises.

10-night Bongos & Breezes Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
St. Vincent (Kingstown)
St. George's
Castries
Fort de France
+5 more

Aboard

Seven Seas Grandeur

From

Bridgetown, Barbados

1 Sailing

Jan 8, 2029

1 Sailing

Jan 8, 2029

Published prices from

$6,999

per person*

taxes & fees included

A scenic Caribbean bay near Kingstown, Saint Vincent and the Grenadines, with small boats anchored in the turquoise water and lush green hillsides with colorful houses.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

10-night Soca At Sea Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
St. George's
Oranjestad
Willemstad
Kralendijk
+4 more

Aboard

Seven Seas Grandeur

From

Bridgetown, Barbados

1 Sailing

Jan 18, 2029

1 Sailing

Jan 18, 2029

Published prices from

$6,999

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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

10-night Current Of Calypso Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
St. Vincent (Kingstown)
St. George's
Castries
Fort de France
+5 more

Aboard

Seven Seas Grandeur

From

Bridgetown, Barbados

1 Sailing

Jan 28, 2029

1 Sailing

Jan 28, 2029

Published prices from

$7,099

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
Oceania Cruises

14-night Windward Wanderer Voyage From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
St. John's
Roseau
Bridgetown (Barbados)
+5 more

Aboard

Oceania Sonata

From

Miami, Florida

1 Sailing

Feb 22, 2029

1 Sailing

Feb 22, 2029

Published prices from

$7,199

per person*

taxes & fees included

Tropical beach with lounge chairs in Cozumel.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Oceania Cruises

21-night Caribbean Icons & Miami Magic Voyage From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
St. John's
Roseau
Bridgetown (Barbados)
+8 more

Aboard

Oceania Sonata

From

Miami, Florida

1 Sailing

Feb 22, 2029

1 Sailing

Feb 22, 2029

Published prices from

$10,299

per person*

taxes & fees included

*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.