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

11-night Eastern Caribbean: Windward & Leeward Islands Cruise

Aboard

Koningsdam

From

Fort Lauderdale, Florida

Published prices from

$2,114

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

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

Aboard

Koningsdam

From

Fort Lauderdale, 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*+ 3 more offers
TCW EXCLUSIVE
Cunard

35-night Eastern Caribbean Cruise

Aboard

Queen Victoria

From

Southampton (London), England

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

10-night Sublime Southern Caribbean 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

14-night Star Collector: Leeward & Windward Caribbean Havens Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

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.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

28-night Star Collector: The Best Of The Windward & Leeward Isles Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

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.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

55-night Star Collector: A Grand Caribbean Adventure Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

An aerial view of Anse Mitan in Martinique, a beautiful Caribbean village with a bustling beach, sailboats moored in the bay, and lush green hills in the distance.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

21-night Star Collector: A Lesser Antilles Odyssey Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

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.
FREE Dining, Onboard Activities & More*+ 1 more offer
Royal Caribbean logo

7-night Southern Caribbean Cruise

Aboard

Brilliance of the Seas

From

San Juan, Puerto Rico

Published prices from

$740

per person*

taxes & fees included

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

11-night Caribbean Cruise

Aboard

Silver Spirit

From

Bridgetown, Barbados

Published prices from

$6,400

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 Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

21-night Caribbean Cruise

Aboard

Silver Spirit

From

Bridgetown, Barbados

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

18-night Vibrant Voyage To Rio - 2026 World Voyage Segment

Aboard

Vista

From

Miami, Florida

Published prices from

$6,399

per person*

taxes & fees included

A scenic view of Devil's Island, a small tropical island in French Guiana, completely covered by a dense forest of palm trees.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Oceania Cruises

60-night Circle South America - 2026 World Voyage Segment

Aboard

Vista

From

Miami, Florida

Published prices from

$17,699

per person*

taxes & fees included

A scenic view of Devil's Island, a small tropical island in French Guiana, completely covered by a dense forest of palm trees.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Oceania Cruises

180-night Around the World Voyage

Aboard

Vista

From

Miami, Florida

Published prices from

$58,099

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

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

19-night Caribbean Tour De Force Voyage

Aboard

Insignia

From

Miami, Florida

Published prices from

$5,749

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 All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

7-night Lush & Lovely Islands of the Lesser Antilles Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$7,136

per person*

taxes & fees included

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

7-night Caribbean Cruise

Aboard

Silver Shadow

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$6,300

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.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

14-night Caribbean Cruise

Aboard

Silver Shadow

From

Philipsburg, St. Maarten, The Netherlands

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: Antilles Adventures Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

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

11-night Best Of Southern Caribbean Cruise

Aboard

Celebrity Ascent

From

Fort Lauderdale, Florida

Published prices from

$2,001

per person*

taxes & fees included

A sunny shot of Mahogany Bay, Roatan, with white sandy beaches, green palm trees, a cruise ship port, and a chairlift.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

21-night Western & Eastern Caribbean: Mexico & Leeward Island Cruise

Aboard

Koningsdam

From

Fort Lauderdale, Florida

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 $2,300 Onboard Credit*+ 1 more offer
Windstar

10-night Blue Waters Of The Leeward Islands Cruise

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

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

17-night Star Collector: Hidden Gems of the Caribbean Cruise

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

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*+ 1 more offer
TCW EXCLUSIVE
Oceania Cruises

31-night Island & Amazon Immersion Voyage

Aboard

Insignia

From

Miami, Florida

Published prices from

$8,549

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.