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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.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Cunard

21-night Caribbean Celebration Cruise

Aboard

Queen Elizabeth

From

Miami, Florida

Published prices from

$2,769

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

A secluded cove with white sand and turquoise water on Half Moon Cay, Bahamas, surrounded by jagged, rocky cliffs and a serene blue ocean under a partly cloudy sky.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

21-night Southern Caribbean & Panama Canal Holiday Cruise

Aboard

Rotterdam

From

Fort Lauderdale, Florida

An aerial view of the Kralendijk waterfront in Bonaire, showcasing the contrast between the deep blue ocean and the shallow turquoise water near the shore, with sailboats anchored offshore.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

9-night Southern Caribbean Holiday: Abc Islands Cruise

Aboard

Rotterdam

From

Fort Lauderdale, 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.
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

A stunning view of Port Elizabeth in Bequia, St. Vincent and the Grenadines, with a sandy beach lined with palm trees and a building on the shore, and numerous sailboats anchored in the calm turquoise bay.
FREE $200 Shipboard Credit & More with Azamara Circle*+ 1 more offer
Azamara logo

8-night Southern Caribbean Voyage

Aboard

Azamara Quest

From

San Juan, Puerto Rico

Published prices from

$2,829

per person*

taxes & fees included

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

Boats on a canal in Fort Lauderdale.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Princess Cruises logo

14-night Caribbean East/West Adventurer Holiday Cruise

Aboard

Majestic 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*+ 2 more offers
TCW EXCLUSIVE
Carnival Cruise Line

8-night Southern Caribbean Cruise

Aboard

Carnival Horizon

From

Miami, Florida

Published prices from

$769

per person*

taxes & fees included

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.
FREE Dining, Onboard Activities & More*+ 1 more offer
Royal Caribbean logo

7-night Southern Caribbean Holiday Cruise

Aboard

Serenade of the Seas

From

Colon, Panama

A wide shot of the spectacular Petrohué Falls near Puerto Montt, Chile, with turquoise water cascading over volcanic rock, set against the backdrop of the snow-capped Osorno Volcano.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Oceania Cruises

77-night Spanning The Americas Voyage - 2026 World Voyage Segment

Aboard

Vista

From

Los Angeles, California

Published prices from

$23,599

per person*

taxes & fees included

A beautiful scenic shot of the colorful, old-world houses and buildings lining the waterfront of the historic port of Honfleur, France.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Oceania Cruises

197-night World Odyssey Voyage

Aboard

Vista

From

Los Angeles, California

Published prices from

$67,349

per person*

taxes & fees included

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

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 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 All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer
Windstar

15-night Star Collector: Merry Christmas & Happy New Years From The Caribbean Cruise

Aboard

Wind Spirit

From

Oranjestad, Aruba, Caribbean

A scenic landscape view of Admiralty Bay in Bequia, St. Vincent and the Grenadines, with dozens of sailboats moored on the vibrant turquoise water, surrounded by lush green hills.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer
Windstar

8-night An ABC Christmas Cruise

Aboard

Wind Spirit

From

Oranjestad, Aruba, Caribbean

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

$691

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

Published prices from

$749

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

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.
FREE Dining, Onboard Activities & More*+ 1 more offer
Royal Caribbean logo

7-night Southern Caribbean Holiday Cruise

Aboard

Serenade of the Seas

From

Cartagena, Colombia

Published prices from

$3,382

per person*

taxes & fees included

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Oceania Cruises

14-night Holiday Havens Voyage

Aboard

Allura

From

Miami, Florida

Published prices from

$22,699

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer
Windstar

7-night Classic Caribbean Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$2,651

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

*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.