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

8-night Eastern Caribbean Cruise

Aboard

Adventure of the Seas

From

Port Canaveral, Florida

Published prices from

$1,431

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Oceania Cruises

10-night Leeward & Windward Gems Voyage

Aboard

Nautica

From

Miami, Florida

Published prices from

$2,720

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 San Juan & The Virgin Islands Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.
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

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
Silversea logo

11-night Eastern Caribbean Cruise

Aboard

Silver Ray

From

Fort Lauderdale, Florida

Published prices from

$9,200

per person*

taxes & fees included

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

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

14-night Eastern Caribbean: Bahamas & San Juan Cruise

Aboard

Nieuw Statendam

From

Fort Lauderdale, Florida

Published prices from

$2,309

per person*

taxes & fees included

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

14-night Eastern/Western Caribbean Adventurer Cruise

Aboard

Star Princess

From

Fort Lauderdale, Florida

A scenic shot of the stunning Seven Mile Beach in Grand Cayman, with a wide, sandy beach, calm turquoise water, and resorts with palm trees under a beautiful blue sky.
75% off 2nd Guest + 3rd, 4th, & 5th Guests Sail FREE + Bonus Savings*+ 2 more offers
Celebrity Cruise Line logo

7-night Key West, Bahamas & Labadee Cruise

Aboard

Celebrity Apex

From

Port Canaveral, Florida

Published prices from

$1,541

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.
FREE Dining, Waterparks, Entertainment & More*
Carnival Cruise Line

8-night Eastern Caribbean Cruise

Aboard

Carnival Vista

From

Port Canaveral, Florida

Published prices from

$629

per person*

taxes & fees included

A sunny, tropical beach on Grand Turk Island with multiple hot air balloons flying over the turquoise water and shoreline.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

7-night Eastern Caribbean: Amber Cove & Bahamas Cruise

Aboard

Nieuw Statendam

From

Fort Lauderdale, Florida

Published prices from

$1,154

per person*

taxes & fees included

A sunny, idyllic beach scene in Amber Cove, Dominican Republic, with a small boat and paddle resting under a palm tree beside the turquoise ocean and a clear blue sky.
FREE Dining, Waterparks, Entertainment & More*
Carnival Cruise Line

8-night Eastern Caribbean Cruise

Aboard

Carnival Sunshine

From

Norfolk, Virginia

Published prices from

$454

per person*

taxes & fees included

A stunning aerial view of the turquoise waters and white-sand beaches around Paradise Island in Nassau, Bahamas, with the Atlantis resort visible in the distance.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Royal Caribbean logo

5-night Eastern Caribbean Cruise

Aboard

Freedom of the Seas

From

Miami, Florida

Published prices from

$489

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.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

14-night Star Collector: Caribbean Explorations Cruise

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

A picturesque view of a small town nestled at the base of a lush, green mountain on Iles des Saintes, Guadeloupe, with boats moored in the deep blue water and fluffy clouds in the sky.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

7-night Classic Caribbean 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

A long, green steel-arched bridge with multiple supports, the Laviolette Bridge, spanning the wide St. Lawrence River near Trois-Rivières, with a grassy riverbank in the foreground.
Save up to 30% on Last Minute Sailings*+ 1 more offer
Seabourn logo

7-night Caribbean Gems Cruise

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

Published prices from

$3,824

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 sunny, tropical beach on Grand Turk Island with multiple hot air balloons flying over the turquoise water and shoreline.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

14-night Western & Eastern Caribbean: Bahamas & San Juan Cruise

Aboard

Eurodam

From

Fort Lauderdale, Florida

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

7-night Eastern Caribbean Cruise With Puerto Rico

Aboard

Sun Princess

From

Fort Lauderdale, Florida

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

14-night Caribbean East/West Adventurer Cruise

Aboard

Sun Princess

From

Fort Lauderdale, Florida

A stunning aerial view of the turquoise waters and white-sand beaches around Paradise Island in Nassau, Bahamas, with the Atlantis resort visible in the distance.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Carnival Cruise Line

7-night Eastern Caribbean Cruise

Aboard

Carnival Celebration

From

Miami, Florida

Published prices from

$564

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
Princess Plus - Drinks, Wi-Fi, Tips Included & More*+ 2 more offers
Princess Cruises logo

8-night Eastern Caribbean With St. Thomas Cruise

Aboard

Sky Princess

From

Port Canaveral, Florida

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 Eastern Caribbean & Perfect Day Cruise

Aboard

Independence of the Seas

From

Miami, Florida

Published prices from

$759

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

6-night Western Caribbean Cruise

Aboard

Allure of the Seas

From

Fort Lauderdale, Florida

Published prices from

$965

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.