Windstar

Windstar Cruises to Caribbean

White sand beach with boulders and palm trees in Virgin Gorda, a beautiful Caribbean destination for a Windstar cruise.

Upcoming Windstar Cruises to Caribbean

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A picturesque view of a red and white lighthouse on a rocky cliff overlooking the vast Atlantic Ocean in St. Anthony, Newfoundland and Labrador.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

25-night Star Collector Cruise: Autumn In Newfoundland And New England From Boston, Massachusetts

Aboard

Star Pride

From

Boston, Massachusetts

A low-angle shot of a massive, imposing cliff face rising dramatically from the dark water, with patches of moss and greenery clinging to its textured, gray rock surface.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

25-night Star Collector Cruise: Autumn In Newfoundland And New England From Montreal, Quebec

Aboard

Star Pride

From

Montreal, Quebec

A stunning autumn landscape in Havre-Saint-Pierre, Quebec, with a lake reflecting a forest of trees in various shades of green, yellow, and orange, with a wooden pier in the foreground.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

14-night Quebec And Newfoundland Adventure Cruise From Montreal, Quebec

Aboard

Star Pride

From

Montreal, Quebec

A breathtaking view of the unique, rocky coastline of St. George's, Bermuda, with a tall rock formation rising from the shallow, clear turquoise waters.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

19-night Star Collector: Fall Leaves & Caribbean Breezes Cruise From Montreal, Quebec

Aboard

Star Pride

From

Montreal, Quebec

The iconic Library of Celsus in the ancient city of Ephesus, Turkey, with its magnificent, two-story facade and marble columns standing against a backdrop of cypress trees and green hills.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

70-night Star Collector: Grand Mediterranean And Latin America Adventure Cruise From Istanbul, Turkey

Aboard

Star Legend

From

Istanbul, Turkey

A turquoise and white ferry boat cruises through the harbor in Hamilton, Bermuda, with a backdrop of pastel-colored buildings and houses along the waterfront.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

8-night Bermuda Bliss Cruise From Boston, Massachusetts

Aboard

Star Pride

From

Boston, Massachusetts

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
Windstar

11-night Gems Of The Leeward Islands Cruise From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

Belém Tower on Tagus River.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

24-night Star Collector: Classic Crossing To Spain & More Cruise From Barcelona, Spain

Aboard

Wind Star

From

Barcelona, Spain

A scenic view of the white sand beach and lush palm trees of Mystery Island, Aneityum, with calm, turquoise water under a clear blue sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

23-night Star Collector Cruise: Spanish Mystery & Atlantic Crossing From Barcelona, Spain

Aboard

Star Legend

From

Barcelona, Spain

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

7-night Windward Islands Surf & Sunsets Cruise From San Juan, Puerto Rico

Aboard

Star Pride

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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

14-night Star Collector: Lovely Leewards Cruise From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

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

14-night Ocean Crossings Cruise From Lisbon, Portugal

Aboard

Wind Star

From

Lisbon, Portugal

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
Windstar

25-night Star Collector: Southern Caribbean Thanksgiving Jubilee Cruise From Lisbon, Portugal

Aboard

Wind Star

From

Lisbon, Portugal

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

22-night Star Collector Cruise: Caribbean Beats & Transatlantic Treats From Malaga, Spain

Aboard

Star Legend

From

Malaga, Spain

A picturesque view of the historic Cape Spartel Lighthouse on a cliff overlooking the Atlantic Ocean near Tangier, Morocco.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

13-night Ocean Crossings Cruise From Malaga, Spain

Aboard

Star Legend

From

Malaga, Spain

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

7-night San Juan & The Virgin Islands Cruise From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

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

18-night Star Collector: Reefs & Rainforests: The Caribbean, Colombia, Panama & Costa Rica Via The Panama Canal Cruise From Bridgetown, Barbados

Aboard

Wind Star

From

Bridgetown, Barbados

Colorful colonial balconies in Cartagena.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

11-night Colombian & Southern Caribbean Coastlines Cruise From Bridgetown, Barbados

Aboard

Wind Star

From

Bridgetown, Barbados

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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

15-night Star Collector: Captivating Caribbean Cruise From Bridgetown, Barbados

Aboard

Star Legend

From

Bridgetown, Barbados

A vibrant panoramic view of Castries, St. Lucia, with colorful buildings nestled along the harbor and lush green hills in the background under a blue sky with white clouds.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

7-night Jewels Of The Windward Islands Cruise From Bridgetown, Barbados

Aboard

Star Legend

From

Bridgetown, Barbados

A breathtaking aerial view of the iconic Pitons, two majestic volcanic peaks, rising from the turquoise waters of the Caribbean Sea on the island of St. Lucia, with a small bay and sailboats.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

16-night Star Collector: Windward Islands & Spanish New World Cruise From Bridgetown, Barbados

Aboard

Star Legend

From

Bridgetown, Barbados

A breathtaking tropical beach on Mayreau Island, Grenadines, with white sand, tall palm trees, and turquoise water under a perfectly blue sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

8-night Windward Ways & Tobago Cays Cruise From Bridgetown, Barbados

Aboard

Star Legend

From

Bridgetown, Barbados

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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

21-night Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing Cruise From Lisbon, Portugal

Aboard

Wind Surf

From

Lisbon, Portugal

An aerial view of Bocas del Toro, a vibrant town on the Caribbean coast of Panama, featuring colorful houses built over clear blue water and numerous sailboats docked nearby.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

8-night Panama Canal, Cartagena, San Blas Islands & More Cruise From Oranjestad, Aruba, Caribbean

Aboard

Star Legend

From

Oranjestad, Aruba, Caribbean

Lush rainforest and beach in Costa Rica.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

16-night Star Collector: Latin America Explorer Cruise From Oranjestad, Aruba, Caribbean

Aboard

Star Legend

From

Oranjestad, Aruba, Caribbean

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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

14-night Star Collector: Caribbean Explorations Cruise From Philipsburg, St. Maarten, The Netherlands

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

7-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise From Philipsburg, St. Maarten, The Netherlands

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

A breathtaking panoramic view of Charlotte Amalie harbor in St. Thomas, with a cruise ship anchored in the bay, surrounded by rolling green hills and a colorful sunset.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

7-night Classic Caribbean Cruise From Philipsburg, St. Maarten, The Netherlands

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

13-night Latin America Explorer Cruise From Puerto Caldera, Costa Rica

Aboard

Star Legend

From

Puerto Caldera, Costa Rica

Colorful colonial balconies in Cartagena.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

6-night Panama Canal, Cartagena, San Blas Islands & More Cruise From Fuerte Amador, Panama

Aboard

Star Legend

From

Fuerte Amador, Panama

A breathtaking aerial view of the iconic Pitons, two majestic volcanic peaks, rising from the turquoise waters of the Caribbean Sea on the island of St. Lucia, with a small bay and sailboats.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

14-night Star Collector: Windward Islands & Spanish New World Cruise From Fuerte Amador, Panama

Aboard

Star Legend

From

Fuerte Amador, Panama

A stunning panoramic view of Rodney Bay on the island of St. Lucia, showing a bustling harbor filled with sailboats, a colorful town, and lush green hills under a bright blue, cloudy sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

8-night Windward Ways & Tobago Cays Cruise From Oranjestad, Aruba, Caribbean

Aboard

Star Legend

From

Oranjestad, Aruba, Caribbean

A beautiful Porto Santo beach landscape with a long stretch of golden sand, a wicker bench, a wooden fence, and the distinctive mountains of Madeira in the background.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

15-night Ocean Crossings Cruise From Bridgetown, Barbados

Aboard

Star Legend

From

Bridgetown, Barbados

A scenic view of the iconic Plaza de España in Seville, Spain, featuring its grand arcade of arches and columns, a main building with a clock tower, and a bright blue sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

23-night Star Collector Cruise: Spanish Shores Transatlantic Crossing From Bridgetown, Barbados

Aboard

Star Legend

From

Bridgetown, Barbados

A low-angle shot of the magnificent Palacio Consistorial, the town hall of Cartagena, Spain, showcasing its ornate, white marble facade and domed rooftops against a blue sky.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

23-night Star Collector: Atlantic Interludes & Iberian Indulgences Cruise From Philipsburg, St. Maarten, The Netherlands

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

A beautiful panoramic shot from a garden in Funchal, Madeira, Portugal, showcasing meticulously manicured flower beds in geometric patterns with the city and the Atlantic Ocean in the background.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

15-night Ocean Crossings Cruise From Philipsburg, St. Maarten, The Netherlands

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Historic Halifax waterfront buildings.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

25-night Star Collector: Autumn In Newfoundland And New England Cruise From Boston, Massachusetts

Aboard

Star Pride

From

Boston, Massachusetts

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

21-night Star Collector: Fall Leaves & Caribbean Breezes Cruise From Montreal, Quebec

Aboard

Star Pride

From

Montreal, Quebec

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
Windstar

17-night Star Collector Cruise: Bermuda & Caribbean Island Explorer From Boston, Massachusetts

Aboard

Star Pride

From

Boston, Massachusetts

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
Windstar

10-night Bermuda Bliss Cruise From Boston, Massachusetts

Aboard

Star Pride

From

Boston, Massachusetts

A beautiful panoramic shot from a garden in Funchal, Madeira, Portugal, showcasing meticulously manicured flower beds in geometric patterns with the city and the Atlantic Ocean in the background.
Up to $500 FREE Onboard Credit*
TCW EXCLUSIVE
Windstar

8-night Ocean Crossings Cruise From Lisbon, Portugal

Aboard

Wind Surf

From

Lisbon, Portugal

The picturesque fishing village of Deshaies, Guadeloupe, with its colorful waterfront and red-roofed church nestled on a tranquil bay.
Up to $500 FREE Onboard Credit*
TCW EXCLUSIVE
Windstar

23-night Star Collector Cruise: Hearty Ports & Rum Punches - A Transatlantic Crossing From Lisbon, Portugal

Aboard

Wind Surf

From

Lisbon, Portugal

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*
TCW EXCLUSIVE
Windstar

8-night Beach Fun & Sun Cruise: A Remote Caribbean Getaway From Philipsburg, St. Maarten, The Netherlands

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.
Up to $500 FREE Onboard Credit*
TCW EXCLUSIVE
Windstar

15-night Star Collector Cruise: Caribbean Explorations From Philipsburg, St. Maarten, The Netherlands

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

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*+ 1 more offer
TCW EXCLUSIVE
Windstar

21-night Star Collector Cruise: Windward Islands, Spanish Cities & Costa Rica From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

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.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

14-night Star Collector Cruise: Caribbean Islands & Colombian Coast Discovery From San Juan, Puerto Rico

Aboard

Star Pride

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.
Up to $500 FREE Onboard Credit*
TCW EXCLUSIVE
Windstar

14-night Star Collector Cruise: Caribbean Explorations From Philipsburg, St. Maarten, The Netherlands

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

14-night Star Collector: Coffee, Canal & Callaloo: Central America, Colombia & The Caribbean Cruise From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

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.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

7-night The Spanish Main: Rise Of The New World Cruise From San Juan, Puerto Rico

Aboard

Star Pride

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
Windstar

7-night Beach Fun & Sun: A Remote Caribbean Getaway From Philipsburg, St. Maarten, The Netherlands

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Belém Tower on Tagus River.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

14-night Ocean Crossings Cruise From Lisbon, Portugal

Aboard

Star Legend

From

Lisbon, Portugal

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

21-night Star Collector Cruise: Atlantic Crossing To The Virgin Islands From Lisbon, Portugal

Aboard

Star Legend

From

Lisbon, Portugal

A snorkeler swims in the turquoise waters of the Baths National Park on Virgin Gorda, surrounded by massive granite boulders and palm trees.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

7-night San Juan & The Virgin Islands Cruise From San Juan, Puerto Rico

Aboard

Star Legend

From

San Juan, Puerto Rico

A breathtaking panoramic view of Cruz Bay, St. John, showcasing a vibrant coastal town with white-sand beaches, clear turquoise waters, and numerous boats in the harbor.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

14-night Star Collector Cruise: Lovely Leewards From San Juan, Puerto Rico

Aboard

Star Legend

From

San Juan, Puerto Rico

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*
TCW EXCLUSIVE
Windstar

13-night Star Collector Cruise: Caribbean Explorations From Philipsburg, St. Maarten, The Netherlands

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

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.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

7-night Windward Islands Surf & Sunsets Cruise From San Juan, Puerto Rico

Aboard

Star Legend

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.
Up to $500 FREE Onboard Credit*
TCW EXCLUSIVE
Windstar

6-night Beach Fun & Sun Cruise: A Remote Caribbean Getaway From Philipsburg, St. Maarten, The Netherlands

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*
TCW EXCLUSIVE
Windstar

7-night Beach Fun & Sun Cruise: A Remote Caribbean Getaway From Philipsburg, St. Maarten, The Netherlands

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

A close-up shot of two cougars, or pumas, resting on a rocky ledge. The cougar in the foreground looks directly at the camera, its tawny-colored face and alert eyes focused, while the other cougar is curled up and resting behind it.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

21-night Star Collector Cruise: Costa Rica, Panama & Aruba From Puerto Caldera, Costa Rica

Aboard

Star Pride

From

Puerto Caldera, Costa Rica

A close-up shot of two cougars, or pumas, resting on a rocky ledge. The cougar in the foreground looks directly at the camera, its tawny-colored face and alert eyes focused, while the other cougar is curled up and resting behind it.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

14-night Star Collector Cruise: Latin America Explorer From Puerto Caldera, Costa Rica

Aboard

Star Pride

From

Puerto Caldera, Costa Rica

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.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

22-night Star Collector Cruise: Caribbean Charms To Iberian Shores From San Juan, Puerto Rico

Aboard

Star Legend

From

San Juan, Puerto Rico

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*+ 1 more offer
TCW EXCLUSIVE
Windstar

14-night Star Collector Cruise: Panama, Aruba & The British Virgin Islands From Balboa, Panama

Aboard

Star Pride

From

Balboa, Panama

A cruise ship navigating through the Gatun Locks of the Panama Canal, an important navigational route and popular tourist destination.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

7-night Panama Canal, Cartagena, San Blas Islands & More Cruise From Balboa, Panama

Aboard

Star Pride

From

Balboa, Panama

An aerial view of Agadir, Morocco, showcasing the city's long sandy beach and curving coastline, with a busy marina and port in the foreground.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

15-night Ocean Crossings Cruise From San Juan, Puerto Rico

Aboard

Star Legend

From

San Juan, Puerto Rico

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.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

21-night Star Collector Cruise: Caribbean Collection: ABC, BVI & The Windwards From Oranjestad, Aruba, Caribbean

Aboard

Star Pride

From

Oranjestad, Aruba, Caribbean

A scenic landscape view of Admiralty Bay in Bequia, St. Vincent and the Grenadines, with dozens of sailboats moored on the vibrant turquoise water, surrounded by lush green hills.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

14-night Star Collector Cruise: Windward Islands, ABC Islands & The Virgin Islands From Oranjestad, Aruba, Caribbean

Aboard

Star Pride

From

Oranjestad, Aruba, Caribbean

A sunny view of the colorful waterfront of Willemstad, Curacao, with its iconic pastel-colored Dutch colonial buildings lining the Handelskade street and a ship docked in the port.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

7-night Island Trails Cruise: Aruba To The Virgin Islands From Oranjestad, Aruba, Caribbean

Aboard

Star Pride

From

Oranjestad, Aruba, Caribbean

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*
TCW EXCLUSIVE
Windstar

22-night Star Collector Cruise: Hearty Ports & Rum Punches - A Transatlantic Crossing From Philipsburg, St. Maarten, The Netherlands

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

A scenic landscape view of Admiralty Bay in Bequia, St. Vincent and the Grenadines, with dozens of sailboats moored on the vibrant turquoise water, surrounded by lush green hills.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

23-night Star Collector Cruise: Tropical Horizons To Historic Amsterdam From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

Tulip fields with traditional windmills, showcasing the beauty of the Netherlands in springtime.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

16-night Ocean Crossings Cruise From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

*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.

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