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An aerial view of the vibrant marina and coastline of Pointe-à-Pitre, Guadeloupe, showing numerous boats docked in the harbor, surrounded by lush green hills and the turquoise Caribbean Sea.
Military Families Save 10%*+ 1 more offer
MSC Cruises logo

7 nights South Caribbean

Aboard

MSC Virtuosa

From

Pointe-à-Pitre, Guadeloupe

Published prices from

$782

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Princess Plus - Drinks, Wi-Fi, Tips Included & More*+ 2 more offers
Princess Cruises logo

14-night Southern Caribbean Adventurer Cruise

Aboard

Grand Princess

From

San Juan, Puerto Rico

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Buy One, Get One FREE Airfare*+ 5 more offers
Norwegian Cruise Line logo.

7-night Caribbean Cruise: Barbados, Antigua & St. Lucia

Aboard

Norwegian Epic

From

San Juan, Puerto Rico

Published prices from

$719

per person*

taxes & fees included

A snorkeler swims in the turquoise waters of the Baths National Park on Virgin Gorda, surrounded by massive granite boulders and palm trees.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

10-night Caribbean Cruise

Aboard

Silver Spirit

From

Bridgetown, Barbados

Published prices from

$7,800

per person*

taxes & fees included

Boats on a canal in Fort Lauderdale.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

21-night Caribbean Cruise

Aboard

Silver Spirit

From

Bridgetown, Barbados

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

9-night Southern Caribbean Cruise

Aboard

Silver Shadow

From

Cartagena, Colombia

Published prices from

$6,900

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

16-night Caribbean Cruise

Aboard

Silver Shadow

From

Cartagena, Colombia

A stunning panoramic view of Road Town on Tortola, British Virgin Islands, showing the harbor filled with boats and a small town surrounded by lush green hills overlooking the Caribbean Sea.
Military Families Save 10%*+ 1 more offer
MSC Cruises logo

14 nights South Caribbean

Aboard

MSC Virtuosa

From

Bridgetown, Barbados

Published prices from

$1,838

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.
Buy One, Get One FREE Airfare*+ 5 more offers
Norwegian Cruise Line logo.

12-night Caribbean Cruise: Curacao, Aruba & Barbados

Aboard

Norwegian Sky

From

Punta Cana, Dominican Republic

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE Wi-Fi, Dining, Spa Access & More*+ 1 more offer
Viking

10-night West Indies Explorer Cruise

Aboard

Viking Sea

From

San Juan, Puerto Rico

Published prices from

$3,699

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.
Save up to 30% on Last Minute Sailings*+ 1 more offer
Seabourn logo

14-night Yachtsman's Island Jewels Cruise

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

A stunning panoramic view of Road Town on Tortola, British Virgin Islands, showing the harbor filled with boats and a small town surrounded by lush green hills overlooking the Caribbean Sea.
Military Families Save 10%*+ 1 more offer
MSC Cruises logo

14 nights Central Caribbean

Aboard

MSC Virtuosa

From

Fort de France, Martinique

A scenic coastal view in Curaçao featuring houses with orange roofs on a cliffside overlooking a rocky beach with beautiful turquoise Caribbean water.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

12-night Circle Caribbean Cruise

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Oceania Cruises

10-night Caribbean Illumination Voyage

Aboard

Allura

From

Miami, Florida

Published prices from

$4,200

per person*

taxes & fees included

A breathtaking underwater view of a coral reef with multiple schools of fish swimming over the colorful and diverse marine ecosystem near Roatan Island, Honduras.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Cunard

21-night Caribbean Cruise

Aboard

Queen Elizabeth

From

Miami, Florida

Published prices from

$2,409

per person*

taxes & fees included

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

11-night Leeward Islands Odyssey Cruise

Aboard

Seven Seas Grandeur

From

Miami, Florida

Boats on a canal in Fort Lauderdale.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Celebrity Cruise Line logo

10-night Ultimate Southern Caribbean Cruise

Aboard

Celebrity Ascent

From

Fort Lauderdale, Florida

Published prices from

$1,705

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
Save up to 30% on Last Minute Sailings*+ 1 more offer
Seabourn logo

7-night Classic Caribbean Yacht Harbors Cruise

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

Published prices from

$4,079

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
Save up to 30% on Last Minute Sailings*+ 1 more offer
Seabourn logo

14-night Exotic Caribbean Isles Cruise

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

Published prices from

$8,146

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
Save 30% on Select Cruises*
MSC Cruises logo

14 nights South Caribbean

Aboard

MSC Virtuosa

From

Fort de France, Martinique

An aerial view of the vibrant marina and coastline of Pointe-à-Pitre, Guadeloupe, showing numerous boats docked in the harbor, surrounded by lush green hills and the turquoise Caribbean Sea.
Military Families Save 10%*+ 1 more offer
MSC Cruises logo

7 nights South Caribbean

Aboard

MSC Virtuosa

From

Fort de France, Martinique

Published prices from

$438

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.
Buy One, Get One FREE Airfare*+ 5 more offers
Norwegian Cruise Line logo.

7-night Caribbean Cruise: Curacao, Aruba & Bonaire

Aboard

Norwegian Sky

From

Punta Cana, Dominican Republic

Published prices from

$789

per person*

taxes & fees included

A stunning panoramic view of Rio de Janeiro's coastline, with the iconic Christ the Redeemer statue in the foreground, Sugarloaf Mountain, and the sprawling city.
Free 2-Category Suite Upgrade + up to $900 Onboard Credit*+ 1 more offer
Regent Seven Seas Cruises.

24-night The Colors of Carnival Cruise

Aboard

Seven Seas Splendor

From

Buenos Aires, Argentina

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Cunard

12-night Eastern Caribbean Cruise

Aboard

Queen Elizabeth

From

Miami, Florida

Published prices from

$1,399

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

14-night Eastern and Southern Caribbean Cruise

Aboard

Silver Shadow

From

Philipsburg, St. Maarten, The Netherlands

*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.