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Boats on a canal in Fort Lauderdale.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

21-night Caribbean Cruise

Aboard

Silver Spirit

From

Bridgetown, Barbados

Rocky beach and palm trees in Barbados.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

16-night Caribbean Cruise

Aboard

Silver Shadow

From

Cartagena, Colombia

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 San Juan & The Virgin Islands Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Published prices from

$6,062

per person*

taxes & fees included

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.
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

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: Caribbean Explorations Cruise

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

A picturesque view of a small town nestled at the base of a lush, green mountain on Iles des Saintes, Guadeloupe, with boats moored in the deep blue water and fluffy clouds in the sky.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

7-night Classic Caribbean Cruise

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

11-night Leeward Islands Odyssey Cruise

Aboard

Seven Seas Grandeur

From

Miami, Florida

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

11-night Caribbean Cruise

Aboard

Silver Spirit

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

7-night Southern Caribbean Cruise

Aboard

Silver Shadow

From

Bridgetown, Barbados

Published prices from

$7,200

per person*

taxes & fees included

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

6-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

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

18-night Star Collector: Deep Dive Into the Blue: Underwater Worlds of the Caribbean Cruise

Aboard

Wind Surf

From

Cozumel, Mexico

Cupecoy Beach with white resort buildings, St. Maarten.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

14-night Eastern and Southern Caribbean Cruise

Aboard

Silver Shadow

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

22-night Star Collector: A Lesser Antilles Odyssey Cruise

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

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

28-night Star Collector: Grand Caribbean & Panamanian Adventure Cruise

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

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: Leeward & Windward Caribbean Havens Cruise

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

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

28-night Transatlantic Cruise

Aboard

Silver Ray

From

San Juan, Puerto Rico

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

14-night Eastern and Southern Caribbean Cruise

Aboard

Silver Ray

From

San Juan, Puerto Rico

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Oceania Cruises

11-night Azure Antilles Voyage

Aboard

Allura

From

Miami, Florida

Published prices from

$4,599

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

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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

14-night A Blissful Escape Cruise

Aboard

Seven Seas Grandeur

From

Miami, Florida

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

$3,051

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

15-night Star Collector: Antilles Adventure 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

14-night Star Collector: Caribbean Explorations Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$4,919

per person*

taxes & fees included

A view of Pigeon Island National Landmark, St. Lucia, showing a lush, green peninsula jutting out into the ocean with waves crashing on the rocks.
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 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

7-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$3,167

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.