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Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 6 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

12-night Caribbean Cruise: Bahamas & St. Thomas

Aboard

Norwegian Gem

From

Jacksonville, Florida

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*+ 3 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

$1,126

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.
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.
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.
Up to $500 FREE Onboard Credit*+ 7 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

10-night Caribbean Cruise: Dominican Republic & Antigua

Aboard

Norwegian Getaway

From

Miami, Florida

Published prices from

$1,099

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

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

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

10-night Southern Caribbean: Amber Cove & Abc Islands Cruise

Aboard

Koningsdam

From

Fort Lauderdale, Florida

Published prices from

$1,899

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
Holland America logo

21-night Southern & Eastern Caribbean: Leeward & U.S. Virgin Islands Cruise

Aboard

Koningsdam

From

Fort Lauderdale, Florida

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

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

20-night Caribbean Explorer Cruise

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

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

Published prices from

$6,062

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.
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

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

$9,600

per person*

taxes & fees included

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 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

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 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.
Military Families Save 10%*+ 1 more offer
MSC Cruises logo

7 nights Central Caribbean

Aboard

MSC Virtuosa

From

Fort de France, Martinique

Published prices from

$721

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.
Save 30% on Select Cruises*
MSC Cruises logo

6 nights Central Caribbean

Aboard

MSC Virtuosa

From

Pointe-Ć -Pitre, Guadeloupe

Published prices from

$2,579

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.
Military Families Save 10%*+ 1 more offer
MSC Cruises logo

7 nights Central Caribbean

Aboard

MSC Virtuosa

From

Pointe-Ć -Pitre, Guadeloupe

Published prices from

$752

per person*

taxes & fees included

A scenic coastal view in CuraƧao 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

*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.