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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

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 $200 Shipboard Credit & More with Azamara Circle*+ 1 more offer
Azamara logo

18-night Eastern Caribbean Voyage

Aboard

Azamara Quest

From

San Juan, Puerto Rico

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

9-night Southern Caribbean Cruise

Aboard

Silver Shadow

From

Cartagena, Colombia

Published prices from

$5,900

per person*

taxes & fees included

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

16-night Caribbean Cruise

Aboard

Silver Shadow

From

Cartagena, Colombia

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
Regent Seven Seas

21-night Island Rhythm and Coastal Charm Cruise

Aboard

Seven Seas Mariner

From

Miami, Florida

A vibrant underwater scene with a large school of tropical fish swimming over a colorful coral reef in the clear, blue waters of the Bahamas.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Regent Seven Seas

14-night Caribbean Quest Cruise

Aboard

Seven Seas Mariner

From

Miami, Florida

Rocky beach and palm trees in Barbados.
Up to 30% off + $250 Onboard Credit + Kids Sail FREE*
MSC Cruises logo

3 nights South Caribbean

Aboard

MSC Virtuosa

From

Fort de France, Martinique

Published prices from

$209

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
Up to 30% off + $250 Onboard Credit + Kids Sail FREE*
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

$519

per person*

taxes & fees included

A classic, two-story colonial building, the Abbey of Our Lady of Exile, with a red roof, a clock tower, and arches in Port of Spain, Trinidad and Tobago, under a cloudy blue sky.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

14-night Eastern Caribbean: Antilles & Private Island Holiday Cruise

Aboard

Volendam

From

Fort Lauderdale, Florida

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

$734

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

$589

per person*

taxes & fees included

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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Regent Seven Seas

12-night Merriment and Joy in the Tropics Cruise

Aboard

Seven Seas Grandeur

From

Miami, 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.
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

$999

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.
Silversea logo

14-night Caribbean Cruise

Aboard

Silver Spirit

From

Bridgetown, Barbados

An aerial view of the colorful waterfront of St. George's, Grenada, with the town's buildings nestled on a hillside and a long, rocky breakwater extending into the calm, turquoise water.
FREE Butler Service, Gourmet Dining & More*
Silversea logo

7-night Caribbean Cruise

Aboard

Silver Spirit

From

Bridgetown, Barbados

Published prices from

$4,300

per person*

taxes & fees included

Tropical beach with lounge chairs in Cozumel.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Holland America logo

32-night Ultimate Caribbean: Leeward Islands Holiday Cruise

Aboard

Zuiderdam

From

Miami, Florida

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
Holland America logo

18-night Eastern & Western Caribbean: Leeward Islands & Mexico Cruise

Aboard

Zuiderdam

From

Miami, Florida

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*+ 2 more offers
TCW EXCLUSIVE
Holland America logo

11-night Eastern Caribbean: Windward & Leeward Islands Holiday Cruise

Aboard

Zuiderdam

From

Miami, Florida

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 view of the volcanic black sand beach and coastline of St. Pierre, Martinique, with colorful buildings and a lush, mountainous landscape under a beautiful sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Azamara logo

14-night Eastern Caribbean Voyage

Aboard

Azamara Onward

From

Miami, Florida

Published prices from

$5,069

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.
FREE $200 Shipboard Credit & More with Azamara Circle*+ 1 more offer
Azamara logo

10-night Eastern Caribbean Voyage

Aboard

Azamara Quest

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

Published prices from

$2,498

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

*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.