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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

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

This is a scenic image of a tropical beach in Santo Domingo, with multiple colorful fishing boats resting on the sandy shore, tall palm trees, and the calm turquoise sea under a bright, clear sky.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 2 more offers
Windstar

11-night Stars of the Greater Antilles Cruise

Aboard

Wind Surf

From

Cozumel, Mexico

Published prices from

$5,313

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.
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

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

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

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

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 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

$5,019

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

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

A scenic view of a pristine beach on the San Blas Islands, Panama, with a line of tall palm trees casting shadows on the white sand and clear turquoise water.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

49-night Star Collector: Grand Caribbean & Americas Explorer Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Published prices from

$35,393

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

10-night Gems Of The Leeward Islands Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Published prices from

$6,757

per person*

taxes & fees included

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

17-night Star Collector: Seeking The Antilles Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Published prices from

$10,084

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

24-night Star Collector: Historic Caribbean: Legendary Islands, Colombia And Panama Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Published prices from

$15,438

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*+ 2 more offers
Windstar

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

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$4,367

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

21-night Star Collector: Spectacular Transatlantic Journey: Caribbean To The Azores Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$6,344

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 $200 Shipboard Credit & More with Azamara Circle*+ 2 more offers
Azamara logo

26-night Canada & Caribbean Voyage: Montreal, Quebec & Barbados

Aboard

Azamara Journey

From

Montreal, Quebec

Published prices from

$7,639

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

11-night Gems Of The Leeward Islands Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$4,257

per person*

taxes & fees included

A beautiful view from Fort King George in Scarborough, Tobago, with historic cannons overlooking the Caribbean Sea and the town below, framed by lush tropical trees.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

16-night Caribbean Voyage: New York, Bermuda & Barbados

Aboard

Azamara Journey

From

New York City, New York

Published prices from

$3,609

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.
FREE $200 Shipboard Credit & More with Azamara Circle*+ 2 more offers
Azamara logo

14-night Caribbean Voyage: San Juan, St. Lucia & St. Kitts

Aboard

Azamara Journey

From

San Juan, Puerto Rico

Published prices from

$3,949

per person*

taxes & fees included

A view of the volcanic black sand beach and coastline of St. Pierre, Martinique, with colorful buildings and a lush, mountainous landscape under a beautiful sky.
FREE $200 Shipboard Credit & More with Azamara Circle*+ 2 more offers
Azamara logo

7-night Southern Caribbean Voyage: Antigua, Grenada & Barbados

Aboard

Azamara Journey

From

San Juan, Puerto Rico

Published prices from

$1,459

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 Pride

From

San Juan, Puerto Rico

Published prices from

$4,993

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 $200 Shipboard Credit & More with Azamara Circle*+ 2 more offers
Azamara logo

14-night Caribbean Voyage: Barbados, St. Lucia & St. Kitts

Aboard

Azamara Journey

From

Bridgetown, Barbados

Published prices from

$4,079

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

7-night San Juan & The Virgin Islands Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$3,162

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.
Military Families Save 10%*+ 1 more offer
MSC Cruises logo

7 nights Dominican Republic

Aboard

MSC Opera

From

La Romana, Dominican Republic

Published prices from

$568

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.