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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 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

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

14-night Star Collector: Captivating Caribbean Cruise

Aboard

Wind Spirit

From

Bridgetown, Barbados

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

$1,274

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*
Seabourn logo

14-night Yachtsman's Island Jewels Cruise

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$16,319

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

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

11-night Eastern Caribbean: Windward & Leeward Islands Cruise

Aboard

Zuiderdam

From

Miami, Florida

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

21-night Eastern & Southern Caribbean: Leeward & Abc Islands Cruise

Aboard

Zuiderdam

From

Miami, Florida

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

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.
Save up to 30% on Last Minute Sailings*
Seabourn logo

7-night Caribbean Gems Cruise

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

Published prices from

$3,399

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

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

An aerial view of the bustling city of Balboa, Panama, with a scenic coastal road alongside a marina and tall modern skyscrapers in the background.
Up to $500 FREE Onboard Credit*+ 4 more offers
TCW EXCLUSIVE
Holland America logo

34-night Panama Canal & Eastern Caribbean Cruise

Aboard

Koningsdam

From

Fort Lauderdale, Florida

Yellow kayak on sandy beach in Puerto Vallarta, Mexico.
Up to $500 FREE Onboard Credit*+ 4 more offers
TCW EXCLUSIVE
Holland America logo

29-night Panama Canal & Eastern Caribbean Cruise

Aboard

Koningsdam

From

Fort Lauderdale, Florida

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*+ 4 more offers
TCW EXCLUSIVE
Holland America logo

12-night Eastern Caribbean: U.S. And British Virgin Islands Cruise

Aboard

Koningsdam

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
Oceania Cruises

10-night Caribbean Illumination Voyage

Aboard

Allura

From

Miami, Florida

Published prices from

$4,320

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
Oceania Cruises

33-night East To Ancient Worlds Voyage

Aboard

Allura

From

Miami, Florida

Published prices from

$11,999

per person*

taxes & fees included

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

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

Rhapsody of the Seas

From

San Juan, Puerto Rico

Published prices from

$432

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*+ 1 more offer
TCW EXCLUSIVE
Royal Caribbean logo

10-night Eastern Caribbean Cruise

Aboard

Vision of the Seas

From

Baltimore, Maryland

Published prices from

$741

per person*

taxes & fees included

A stone lion statue in the foreground with the beautiful city of Perast and the Bay of Kotor in Montenegro in the background, featuring red-roofed buildings and a church steeple by the water.
Up to 40% off + 2-Category Upgrade + Your Choice Bonus*
Oceania Cruises

57-night Old & New World Discovery Voyage

Aboard

Insignia

From

Fusina, Venice, Italy

Published prices from

$16,649

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*+ 2 more offers
TCW EXCLUSIVE
Holland America logo

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

Aboard

Zuiderdam

From

Miami, Florida

Published prices from

$3,109

per person*

taxes & fees included

A beautiful sailboat rests in the shallow, clear turquoise waters off the coast of Belize City, with lush palm trees and colorful buildings lining the shore.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

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

Aboard

Rotterdam

From

Fort Lauderdale, Florida

Published prices from

$3,284

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*+ 2 more offers
TCW EXCLUSIVE
Holland America logo

11-night Eastern Caribbean Cruise: Windward & Leeward Islands

Aboard

Zuiderdam

From

Miami, Florida

Published prices from

$1,527

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.