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A scenic view of Forte de São João Baptista, a fortress built on a rocky islet in the Berlengas Archipelago, connected by a stone causeway over turquoise water.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

7-night 2026 President’s Mystery Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Published prices from

$6,862

per person*

taxes & fees included

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

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

Tulip fields with traditional windmills, showcasing the beauty of the Netherlands in springtime.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

16-night Ocean Crossings Cruise

Aboard

Star Pride

From

Bridgetown, Barbados

Published prices from

$4,014

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

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

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

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

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

25-night Star Collector: Classic Crossing To Spain & More Cruise

Aboard

Wind Spirit

From

Bridgetown, Barbados

Published prices from

$6,590

per person*

taxes & fees included

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

15-night Ocean Crossings Cruise

Aboard

Wind Spirit

From

Bridgetown, Barbados

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

$4,567

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

$6,894

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

14-night Ocean Crossings + Ponta Delgada, Azores Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$3,426

per person*

taxes & fees included

A historic fortress, the Castle of La Calahorra, stands on a hilltop overlooking a town with white-washed houses below, under a blue sky with scattered clouds in Almería, Spain.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

22-night Star Collector: Atlantic Interludes & Iberian Indulgences Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$7,148

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

22-night Star Collector Cruise: Central American Explorations Via The Panama Canal

Aboard

Star Seeker

From

San Juan, Puerto Rico

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

7-night New World Caribbean Trio Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Published prices from

$4,826

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

14-night Star Collector: Rainforest Refuges Of Panama & Costa Rica Via The Panama Canal Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

A vibrant orange and red sunset over the tranquil harbor in Sydney, Nova Scotia, with the setting sun reflecting on the water.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

25-night Star Collector Cruise: Autumn In Newfoundland And New England

Aboard

Star Pride

From

Boston, Massachusetts

Published prices from

$18,525

per person*

taxes & fees included

A beautiful shot of the rocky coastline of Baie-Comeau, a port city in Quebec, Canada, with rugged cliffs covered in pine trees meeting the calm, reflective waters of the bay.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

25-night Star Collector Cruise: Autumn In Newfoundland And New England

Aboard

Star Pride

From

Montreal, Quebec

Published prices from

$18,425

per person*

taxes & fees included

A charming white and red lighthouse, perched on a dramatic red cliff overlooking the ocean, with lush green grass and a few houses under a bright blue sky on Cap-aux-Meules, Quebec.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

14-night Quebec And Newfoundland Adventure Cruise

Aboard

Star Pride

From

Montreal, Quebec

Published prices from

$6,669

per person*

taxes & fees included

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

19-night Star Collector: Fall Leaves & Caribbean Breezes Cruise

Aboard

Star Pride

From

Montreal, Quebec

Published prices from

$8,922

per person*

taxes & fees included

Blue Mosque and historic Istanbul skyline with Bosphorus Strait.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

70-night Star Collector: Grand Mediterranean And Latin America Adventure Cruise

Aboard

Star Legend

From

Istanbul, Turkey

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

8-night Bermuda Bliss Cruise

Aboard

Star Pride

From

Boston, Massachusetts

Published prices from

$2,926

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.