301 Results

Sort

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

11-night Southern Caribbean Islander Cruise

Aboard

Grand Princess

From

San Juan, Puerto Rico

Puntarenas, Costa Rica tropical landscape with palm trees and mountains.
Princess Plus - Drinks, Wi-Fi, Tips Included & More*+ 2 more offers
Princess Cruises logo

27-night Panama Canal and Caribbean Adventurer Cruise

Aboard

Grand Princess

From

San Juan, Puerto Rico

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.
FREE Dining, Onboard Activities & More*+ 1 more offer
Royal Caribbean logo

7-night Southern Caribbean Cruise

Aboard

Brilliance of the Seas

From

San Juan, Puerto Rico

Published prices from

$1,411

per person*

taxes & fees included

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

11-night Best Of Southern Caribbean Cruise

Aboard

Celebrity Ascent

From

Fort Lauderdale, Florida

Published prices from

$2,051

per person*

taxes & fees included

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.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

10-night Eastern Caribbean With Tortola Cruise

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

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
Princess Cruises logo

20-night Caribbean Explorer Cruise

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

A scenic view of Princess Cays, Bahamas, featuring a row of colorful cabanas with thatched roofs, surrounded by swaying palm trees on a white-sand beach.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

7-night Eastern Caribbean with Bahamas Cruise

Aboard

Regal Princess

From

Fort Lauderdale, Florida

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
75% off 2nd Guest + 3rd, 4th, & 5th Guests Sail FREE + Bonus Savings*+ 2 more offers
Celebrity Cruise Line logo

7-night St. Kitts, San Juan & Puerto Plata Cruise

Aboard

Celebrity Apex

From

Port Canaveral, Florida

Published prices from

$1,819

per person*

taxes & fees included

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

8-night Antigua, St. Kitts, & San Juan Cruise

Aboard

Celebrity Eclipse

From

Fort Lauderdale, Florida

Published prices from

$1,263

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*+ 4 more offers
TCW EXCLUSIVE
Celebrity Cruise Line logo

7-night St. Thomas, St. Kitts & Puerto Plata Cruise

Aboard

Celebrity Beyond

From

Miami, Florida

Published prices from

$1,349

per person*

taxes & fees included

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: Curacao, Aruba & Bonaire

Aboard

Norwegian Epic

From

San Juan, Puerto Rico

Published prices from

$1,229

per person*

taxes & fees included

Baltimore Inner Harbor skyline at dusk.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Royal Caribbean logo

12-night Southern Caribbean Cruise

Aboard

Vision of the Seas

From

Baltimore, Maryland

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, Onboard Activities & More*+ 1 more offer
Royal Caribbean logo

7-night Eastern Caribbean Cruise

Aboard

Brilliance of the Seas

From

San Juan, Puerto Rico

Published prices from

$2,348

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.
FREE Dining, Onboard Activities & More*+ 1 more offer
Royal Caribbean logo

6-night Southern Caribbean Cruise

Aboard

Jewel of the Seas

From

San Juan, Puerto Rico

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 Dining, Onboard Activities & More*+ 1 more offer
Royal Caribbean logo

7-night Eastern Caribbean Cruise

Aboard

Jewel of the Seas

From

San Juan, Puerto Rico

Published prices from

$1,203

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
Royal Caribbean logo

8-night Eastern Caribbean Cruise

Aboard

Allure of the Seas

From

Fort Lauderdale, Florida

Published prices from

$1,346

per person*

taxes & fees included

An aerial view of a luxurious resort and pristine sandy beach on the coast of Puerto Plata, Dominican Republic, with turquoise waters, lush green hills, and a cityscape in the background.
Up to $500 FREE Onboard Credit*+ 4 more offers
TCW EXCLUSIVE
Celebrity Cruise Line logo

7-nights St. Thomas & Puerto Plata Cruise

Aboard

Celebrity Beyond

From

Miami, Florida

Published prices from

$14,616

per person*

taxes & fees included

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

8-night Eastern Caribbean & Perfect Day Cruise

Aboard

Allure of the Seas

From

Fort Lauderdale, Florida

Published prices from

$1,014

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 4 more offers
TCW EXCLUSIVE
Celebrity Cruise Line logo

7-night St. Thomas, St. Kitts & Perfect Day Cruise

Aboard

Celebrity Beyond

From

Miami, Florida

Published prices from

$1,540

per person*

taxes & fees included

An aerial view of a luxurious resort and pristine sandy beach on the coast of Puerto Plata, Dominican Republic, with turquoise waters, lush green hills, and a cityscape in the background.
Up to $500 FREE Onboard Credit*+ 4 more offers
TCW EXCLUSIVE
Celebrity Cruise Line logo

7-nights Tortola, St. Kitts & Puerto Plata Cruise

Aboard

Celebrity Beyond

From

Miami, Florida

Published prices from

$1,196

per person*

taxes & fees included

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

14-night Circle Caribbean Cruise

Aboard

Coral Princess

From

Fort Lauderdale, Florida

An elevated panoramic shot of the beautiful Ocho Rios Bay in Jamaica, showing a large cruise ship docked at the pier, a sandy beach, and luxury resorts under a blue sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Carnival Cruise Line

14-night Carnival Journeys Cruise - Eastern Caribbean

Aboard

Carnival Dream

From

Galveston, Texas

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

25-night Canada & Caribbean Cruise

Aboard

Silver Shadow

From

Montreal, Quebec

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*
TCW EXCLUSIVE
Oceania Cruises

14-night Caribbean Enchantment Voyage

Aboard

Vista

From

New York City, New York

Published prices from

$4,999

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*+ 1 more offer
Windstar

11-night Gems Of The Leeward Islands Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$4,257

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.