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A historic brick structure with multiple arches and a fountain visible through the center, in a sunny plaza in Chiapas, Mexico.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

16-night Panama Canal - Ocean To Ocean Cruise

Aboard

Island Princess

From

Los Angeles, California

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

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

The ancient stone ruins of a majestic Mayan temple or pyramid, featuring historic architecture at an archaeological site in Mexico's Costa Maya region.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Cunard

9-night Western Caribbean Cruise

Aboard

Queen Elizabeth

From

Miami, Florida

Published prices from

$1,099

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

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

11-night Caribbean Cruise

Aboard

Silver Spirit

From

Fort Lauderdale, Florida

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.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

7-night Southern Caribbean Cruise

Aboard

Silver Shadow

From

Bridgetown, Barbados

Boats on a canal in Fort Lauderdale.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Celebrity Cruise Line logo

10-night Ultimate Southern Caribbean Cruise

Aboard

Celebrity Ascent

From

Fort Lauderdale, Florida

Published prices from

$1,577

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

7-night Windward Islands Surf & Sunsets Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Published prices from

$5,733

per person*

taxes & fees included

A high-angle view of the bustling harbor of Marigot, St. Martin, with boats and yachts docked along the coast and colorful buildings nestled against the green hills.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

14-night Star Collector: Lovely Leewards Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Published prices from

$11,296

per person*

taxes & fees included

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Carnival Cruise Line

8-night Southern Caribbean Cruise

Aboard

Carnival Horizon

From

Miami, Florida

Published prices from

$599

per person*

taxes & fees included

Boats on a canal in Fort Lauderdale.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

11-night Eastern Caribbean: Windward & Leeward Islands Cruise

Aboard

Koningsdam

From

Fort Lauderdale, Florida

Published prices from

$2,114

per person*

taxes & fees included

Immaculate Conception Cathedral in Colon.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Royal Caribbean logo

7-night Southern Caribbean Cruise

Aboard

Serenade of the Seas

From

Colon, Panama

Published prices from

$1,480

per person*

taxes & fees included

An aerial view of the historic town of Falmouth, Jamaica, showing a coastal promenade along the turquoise sea, colorful colonial-era buildings, and lush green hills in the background.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

21-night Eastern & Western Caribbean: Mexico Cruise

Aboard

Koningsdam

From

Fort Lauderdale, Florida

Cupecoy Beach with white resort buildings, St. Maarten.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

6-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE Dining, Onboard Activities & More*+ 1 more offer
Royal Caribbean logo

7-night Southern Caribbean Cruise

Aboard

Jewel of the Seas

From

San Juan, Puerto Rico

Published prices from

$943

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

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*+ 6 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

10-night Caribbean Cruise: Curacao, Aruba & Dominican Republic

Aboard

Norwegian Dawn

From

Tampa, Florida

Colorful colonial balconies in Cartagena.
FREE Dining, Onboard Activities & More*+ 1 more offer
Royal Caribbean logo

7-night Southern Caribbean Cruise

Aboard

Serenade of the Seas

From

Cartagena, Colombia

Published prices from

$1,638

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

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.
Princess Plus - Drinks, Wi-Fi, Tips Included & More*+ 2 more offers
Princess Cruises logo

7-night Southern Caribbean with Barbados 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

Sunshine Skyway Bridge near Tampa, Florida at sunset.
Up to $500 FREE Onboard Credit*+ 6 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

10-night Caribbean Cruise: Curacao, Aruba & Dominican Republic

Aboard

Norwegian Star

From

Tampa, Florida

Published prices from

$839

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*+ 1 more offer
TCW EXCLUSIVE
Oceania Cruises

10-night Caribbean Horizons Voyage

Aboard

Nautica

From

Miami, Florida

Published prices from

$2,550

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.