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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

Windstar

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

Sydney (Nova Scotia)

Aboard

Star Pride

From

Montreal, Quebec

1 Sailing

Oct 9, 2026

1 Sailing

Oct 9, 2026

Published prices from

$9,143

per person*

taxes & fees included

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

Windstar

8-night Bermuda Bliss Cruise From Boston, Massachusetts

Aboard

Star Pride

From

Boston, Massachusetts

1 Sailing

Oct 20, 2026

1 Sailing

Oct 20, 2026

Published prices from

$3,067

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.

Up to $500 FREE Onboard Credit*+ 2 more offers

Windstar

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

Falmouth Harbour

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Oct 28, 2026

1 Sailing

Oct 28, 2026

Published prices from

$5,118

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.

Up to $500 FREE Onboard Credit*+ 2 more offers

Windstar

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

Iles des Saintes

Aboard

Star Pride

From

San Juan, Puerto Rico

9 Sailings

Nov 8, 2026 - Mar 27, 2028

9 Sailings

Nov 8, 2026 - Mar 27, 2028

Published prices from

$2,411

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.

Up to $500 FREE Onboard Credit*+ 2 more offers

Windstar

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

St. Maarten (Philipsburg)

Aboard

Star Pride

From

San Juan, Puerto Rico

14 Sailings

Nov 8, 2026 - Mar 20, 2028

14 Sailings

Nov 8, 2026 - Mar 20, 2028

Published prices from

$3,902

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.

Up to $500 FREE Onboard Credit*+ 2 more offers

Windstar

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

St. Maarten (Philipsburg)

Aboard

Star Pride

From

San Juan, Puerto Rico

8 Sailings

Nov 15, 2026 - Mar 20, 2028

8 Sailings

Nov 15, 2026 - Mar 20, 2028

Published prices from

$2,443

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.

Up to $500 FREE Onboard Credit*+ 2 more offers

Windstar

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

St. Maarten (Philipsburg)

Falmouth Harbour

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Dec 5, 2026

1 Sailing

Dec 5, 2026

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

Windstar

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

St. Maarten (Philipsburg)

Falmouth Harbour

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

13 Sailings

Dec 19, 2026 - Mar 13, 2027

13 Sailings

Dec 19, 2026 - Mar 13, 2027

Published prices from

$5,216

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

Up to $500 FREE Onboard Credit*+ 2 more offers

Windstar

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

St. Maarten (Philipsburg)

Falmouth Harbour

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

7 Sailings

Dec 19, 2026 - Mar 13, 2027

7 Sailings

Dec 19, 2026 - Mar 13, 2027

Published prices from

$2,560

per person*

taxes & fees included

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

Windstar

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

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

15 Sailings

Dec 26, 2026 - Mar 5, 2028

15 Sailings

Dec 26, 2026 - Mar 5, 2028

Published prices from

$2,362

per person*

taxes & fees included

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

Windstar

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

St. Maarten (Philipsburg)

Funchal (Madeira)

Seville (Cadiz)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Mar 27, 2027

1 Sailing

Mar 27, 2027

Published prices from

$5,230

per person*

taxes & fees included

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

Windstar

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

St. Maarten (Philipsburg)

Funchal (Madeira)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Mar 27, 2027 - Mar 19, 2028

2 Sailings

Mar 27, 2027 - Mar 19, 2028

Published prices from

$2,580

per person*

taxes & fees included

Tulip fields with traditional windmills, showcasing the beauty of the Netherlands in springtime.

Up to $500 FREE Onboard Credit*+ 1 more offer

Windstar

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

Aboard

Star Pride

From

San Juan, Puerto Rico

2 Sailings

Mar 30, 2027 - Apr 3, 2028

2 Sailings

Mar 30, 2027 - Apr 3, 2028

Published prices from

$2,760

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.

Up to $500 FREE Onboard Credit*+ 1 more offer

Windstar

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

Sydney (Nova Scotia)

Halifax (Nova Scotia)

Aboard

Star Pride

From

Montreal, Quebec

1 Sailing

Oct 11, 2027

1 Sailing

Oct 11, 2027

Published prices from

$8,359

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.

Up to $500 FREE Onboard Credit*+ 1 more offer

Windstar

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

Aboard

Star Pride

From

Boston, Massachusetts

1 Sailing

Oct 22, 2027

1 Sailing

Oct 22, 2027

Published prices from

$5,434

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.

Up to $500 FREE Onboard Credit*+ 1 more offer

Windstar

10-night Bermuda Bliss Cruise From Boston, Massachusetts

Aboard

Star Pride

From

Boston, Massachusetts

1 Sailing

Oct 22, 2027

1 Sailing

Oct 22, 2027

Published prices from

$4,327

per person*

taxes & fees included

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*

Windstar

8-night Ocean Crossings Cruise From Lisbon, Portugal

Funchal (Madeira)

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Nov 5, 2027

1 Sailing

Nov 5, 2027

Published prices from

$2,580

per person*

taxes & fees included

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*

Windstar

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

Funchal (Madeira)

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Nov 5, 2027

1 Sailing

Nov 5, 2027

Published prices from

$4,602

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

Up to $500 FREE Onboard Credit*

Windstar

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

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Nov 20 - Dec 19, 2027

2 Sailings

Nov 20 - Dec 19, 2027

Published prices from

$3,148

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.

Up to $500 FREE Onboard Credit*

Windstar

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

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

3 Sailings

Nov 20 - Dec 19, 2027

3 Sailings

Nov 20 - Dec 19, 2027

Published prices from

$4,572

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.

Up to $500 FREE Onboard Credit*+ 1 more offer

Windstar

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

Iles des Saintes

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 22, 2027

1 Sailing

Nov 22, 2027

Published prices from

$6,361

per person*

taxes & fees included

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

Windstar

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

Iles des Saintes

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 22, 2027

1 Sailing

Nov 22, 2027

Published prices from

$3,875

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.

Up to $500 FREE Onboard Credit*

Windstar

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

St. Maarten (Philipsburg)

Iles des Saintes

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

11 Sailings

Nov 28, 2027 - Mar 5, 2028

11 Sailings

Nov 28, 2027 - Mar 5, 2028

Published prices from

$3,872

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.

Up to $500 FREE Onboard Credit*+ 1 more offer

Windstar

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

Catalina Island/Casa de Campo

Cartagena (Colombia)

San Blas Islands

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 29, 2027

1 Sailing

Nov 29, 2027

Published prices from

$4,426

per person*

taxes & fees included

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

Windstar

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

Catalina Island/Casa de Campo

Cartagena (Colombia)

San Blas Islands

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 29, 2027

1 Sailing

Nov 29, 2027

Published prices from

$2,416

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.