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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.
Buy One, Get One FREE Airfare*+ 5 more offers
Norwegian Cruise Line logo.

7-night Caribbean Cruise: Great Stirrup Cay & Dominican Republic

Aboard

Norwegian Joy

From

Port Canaveral, Florida

Published prices from

$879

per person*

taxes & fees included

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

$1,030

per person*

taxes & fees included

A scenic view of Forte de São João Baptista, a fortress built on a rocky islet in the Berlengas Archipelago, connected by a stone causeway over turquoise water.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

7-night 2026 President’s Mystery Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Published prices from

$6,862

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

Published prices from

$4,606

per person*

taxes & fees included

Peaceful sunrise over a sandy Florida beach with sea oats in Port Canaveral.
FREE Dining, Waterparks, Entertainment & More*+ 1 more offer
Carnival Cruise Line

7-night Eastern Caribbean Cruise

Aboard

Mardi Gras

From

Port Canaveral, Florida

Published prices from

$514

per person*

taxes & fees included

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 Eastern Caribbean Cruise

Aboard

Carnival Magic

From

Miami, Florida

Published prices from

$529

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.
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

$2,059

per person*

taxes & fees included

A stunning underwater view of two sea turtles swimming gracefully in the crystal-clear turquoise waters of the Bahamas, with a small island visible in the background.
FREE Dining, Waterparks, Entertainment & More*+ 1 more offer
Carnival Cruise Line

8-night Southern Caribbean Cruise

Aboard

Carnival Vista

From

Port Canaveral, Florida

Published prices from

$589

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
Holland America logo

14-night Eastern Caribbean: Bahamas & San Juan Cruise

Aboard

Nieuw Statendam

From

Fort Lauderdale, Florida

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*+ 4 more offers
TCW EXCLUSIVE
Holland America logo

7-night Eastern Caribbean: Amber Cove & Bahamas Cruise

Aboard

Nieuw Statendam

From

Fort Lauderdale, Florida

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*+ 1 more offer
Carnival Cruise Line

8-night Eastern Caribbean Cruise

Aboard

Carnival Sunshine

From

Norfolk, Virginia

Published prices from

$434

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

Rocky beach and palm trees in Barbados.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

22-night Star Collector: Caribbean Beats & Transatlantic Treats Cruise

Aboard

Wind Spirit

From

Bridgetown, Barbados

Rocky beach and palm trees in Barbados.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

7-night Jewels of the Windward Islands Cruise

Aboard

Wind Spirit

From

Bridgetown, Barbados

Cupecoy Beach with white resort buildings, St. Maarten.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

7-night Classic Caribbean Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$2,851

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 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 Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$5,519

per person*

taxes & fees included

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

$1,235

per person*

taxes & fees included

A view of the stunning architecture of the Hassan II Mosque in Casablanca, Morocco, featuring a long series of ornate stone arches and a spacious courtyard.
Save up to 30% on Last Minute Sailings*+ 1 more offer
Seabourn logo

27-night Caribbean & Atlantic Passage Cruise

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

Cupecoy Beach with white resort buildings, St. Maarten.
Save up to 30% on Last Minute Sailings*+ 1 more offer
Seabourn logo

7-night Classic Caribbean Yacht Harbors Cruise

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

Published prices from

$4,499

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
Save up to 30% on Last Minute Sailings*+ 1 more offer
Seabourn logo

14-night Exotic Caribbean Isles Cruise

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

Published prices from

$8,999

per person*

taxes & fees included

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*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

12-night Caribbean Islander Cruise

Aboard

Regal Princess

From

Galveston, Texas

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
Princess Cruises logo

7-night Eastern Caribbean With St. Thomas Cruise

Aboard

Majestic Princess

From

Fort Lauderdale, Florida

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
Princess Cruises logo

12-night Eastern Caribbean Adventurer Cruise

Aboard

Majestic 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*+ 2 more offers
TCW EXCLUSIVE
Carnival Cruise Line

7-night Eastern Caribbean Cruise

Aboard

Carnival Celebration

From

Miami, Florida

Published prices from

$479

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.