Eastern Caribbean Cruise Deals

View of an Eastern Caribbean beach with soft sand and gentle waves lapping at the shore.

Upcoming Eastern Caribbean Cruise Deals

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

10-night Eastern Caribbean Cruise

Aboard

Silver Ray

From

Fort Lauderdale, Florida

Published prices from

$8,900

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

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Cunard

12-night Eastern Caribbean Cruise

Aboard

Queen Elizabeth

From

Miami, Florida

Published prices from

$1,399

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.
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

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 Windward Islands Surf & Sunsets Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Published prices from

$5,733

per person*

taxes & fees included

A high-angle view of the bustling harbor of Marigot, St. Martin, with boats and yachts docked along the coast and colorful buildings nestled against the green hills.
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

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
Princess Cruises logo

14-night Circle Caribbean Cruise

Aboard

Majestic Princess

From

Fort Lauderdale, Florida

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

14-night Eastern/Western Caribbean Adventurer Cruise

Aboard

Star Princess

From

Fort Lauderdale, Florida

Published prices from

$9,100

per person*

taxes & fees included

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

7-night Eastern Caribbean With Bahamas Cruise

Aboard

Star Princess

From

Fort Lauderdale, Florida

Published prices from

$11,454

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 Southern Caribbean Cruise

Aboard

Carnival Horizon

From

Miami, Florida

Published prices from

$669

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

$604

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Active & Retired Military Members Save up to $200*+ 1 more offer
Celebrity Cruise Line logo

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

Aboard

Celebrity Apex

From

Port Canaveral, Florida

Published prices from

$1,558

per person*

taxes & fees included

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

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

Aboard

Celebrity Eclipse

From

Fort Lauderdale, Florida

Published prices from

$1,231

per person*

taxes & fees included

Tropical beach with lounge chairs in Cozumel.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

14-night Western & Eastern Caribbean: Mexico & Bahamas Cruise

Aboard

Nieuw Statendam

From

Fort Lauderdale, Florida

Published prices from

$2,434

per person*

taxes & fees included

A view of a huge sign that reads "Perfect Day at CocoCay," a private island in the Bahamas, with turquoise water and palm trees under a bright blue sky.
FREE Dining, Onboard Activities & More*+ 1 more offer
Royal Caribbean logo

6-night Western Caribbean & Perfect Day Cruise

Aboard

Adventure of the Seas

From

Port Canaveral, Florida

Published prices from

$631

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

$1,212

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*+ 2 more offers
TCW EXCLUSIVE
Royal Caribbean logo

7-Night Eastern Caribbean & Perfect Day Cruise

Aboard

Icon of the Seas

From

Miami, Florida

Published prices from

$1,481

per person*

taxes & fees included

An aerial view of Road Bay, Anguilla, showing a pristine white sand beach, lush green vegetation, and the stunningly clear turquoise water of the Caribbean Sea.
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

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 Beach Fun & Sun: A Remote Caribbean Getaway Cruise

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

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

$1,002

per person*

taxes & fees included

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.
Save up to 30% on Last Minute Sailings*+ 1 more offer
Seabourn logo

14-night Yachtsman's Island Jewels Cruise

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$7,649

per person*

taxes & fees included

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

7-night Yachtsman's Caribbean Cruise

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$4,079

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

7-night Eastern Caribbean: San Juan & St. Thomas Cruise

Aboard

Eurodam

From

Fort Lauderdale, Florida

Published prices from

$1,304

per person*

taxes & fees included

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
Holland America logo

14-night Eastern & Western Caribbean: San Juan & Mexico Cruise

Aboard

Eurodam

From

Fort Lauderdale, Florida

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

*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.

More to Explore

Cruise Lines

AmaWaterways

MSC Cruises

Norwegian Cruise Line

Avalon Waterways River Cruises

Viking River Cruises

Destinations

Mexico

Transpacific

Eastern Caribbean

Transatlantic

Arctic Circle

Ports

Cai Be, Vietnam

Fredericia, Denmark

Hamina, Finland

Maransabadi Island, Indonesia

Abbotsford, Scotland

Cruise Ships

Delfin III

MSC Bellissima

Carnival Magic

AmaSerena

MSC Meraviglia