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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

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

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

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

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 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 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 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

*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.