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Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE Champagne, Entertainment, Dining & More*
Windstar

7-night San Juan & The Virgin Islands Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.
FREE Champagne, Entertainment, Dining & More*
Windstar

14-night Star Collector: Lovely Leewards Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

A snorkeler swims in the turquoise waters of the Baths National Park on Virgin Gorda, surrounded by massive granite boulders and palm trees.
FREE Champagne, Entertainment, Dining & More*
Windstar

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

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$3,267

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 Champagne, Entertainment, Dining & More*
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

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 Champagne, Entertainment, Dining & More*
Windstar

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

Aboard

Star Seeker

From

San Juan, Puerto Rico

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 Champagne, Entertainment, Dining & More*
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 Champagne, Entertainment, Dining & More*
Windstar

17-night Star Collector: Seeking The Antilles Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Published prices from

$16,984

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 Champagne, Entertainment, Dining & More*
Windstar

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

Aboard

Star Seeker

From

San Juan, Puerto Rico

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.
FREE Champagne, Entertainment, Dining & More*+ 1 more offer
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 Champagne, Entertainment, Dining & More*
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*+ 1 more offer
Azamara logo

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

Aboard

Azamara Journey

From

Montreal, Quebec

Published prices from

$7,969

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 Champagne, Entertainment, Dining & More*
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*+ 2 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

$3,929

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*+ 1 more offer
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*+ 1 more offer
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 Champagne, Entertainment, Dining & More*
Windstar

14-night Star Collector: Lovely Leewards Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$4,593

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*+ 1 more offer
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 Champagne, Entertainment, Dining & More*
Windstar

7-night San Juan & The Virgin Islands Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$2,862

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

"A picturesque white sand beach in La Romana, Dominican Republic, with a distinctive black and white striped lighthouse and a wooden pier extending over the clear turquoise water. "
Military Families Save 10%*+ 1 more offer
MSC Cruises logo

14 nights Dominican Republic

Aboard

MSC Opera

From

Bridgetown, Barbados

Published prices from

$1,258

per person*

taxes & fees included

A stunning view of Port Elizabeth in Bequia, St. Vincent and the Grenadines, with a sandy beach lined with palm trees and a building on the shore, and numerous sailboats anchored in the calm turquoise bay.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

15-night Southern Caribbean In Depth Cruise

Aboard

Seabourn Ovation

From

Miami, Florida

Published prices from

$6,544

per person*

taxes & fees included

A scenic view of Catalina Island, Dominican Republic, with a pristine sandy beach lined with palm trees and the calm turquoise waters of the Caribbean Sea in the background.
Military Families Save 10%*+ 1 more offer
MSC Cruises logo

14 nights Dominican Republic

Aboard

MSC Opera

From

Fort de France, Martinique

Published prices from

$1,248

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.
FREE $200 Shipboard Credit & More with Azamara Circle*+ 1 more offer
Azamara logo

14-night Caribbean Voyage: San Juan, Antigua & Barbados

Aboard

Azamara Journey

From

San Juan, Puerto Rico

Published prices from

$3,899

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*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

14-night Leeward Island Jewels Cruise

Aboard

Seabourn Quest

From

Miami, Florida

Published prices from

$5,524

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
FREE $200 Shipboard Credit & More with Azamara Circle*+ 1 more offer
Azamara logo

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

Aboard

Azamara Journey

From

Bridgetown, Barbados

Published prices from

$3,539

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.