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71 Results

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    • Showing results 1 - 24 of 71

Offramp
Rocky beach and palm trees in Barbados.
FREE Champagne, Entertainment, Dining & More*
Windstar

7-night Windward Ways & Tobago Cays Cruise

Bridgetown (Barbados)
Man O'War Bay
Mayreau
Soufriere
Kralendijk
+3 more

Aboard

Wind Surf

From

Bridgetown, Barbados

1 Sailing

Jan 25, 2026

1 Sailing

Jan 25, 2026

*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.

Cupecoy Beach with white resort buildings, St. Maarten.
FREE Champagne, Entertainment, Dining & More*
Windstar

14-night Star Collector: Leeward & Windward Caribbean Havens Cruise

St. Maarten (Philipsburg)
Falmouth Harbour
Road Bay
Sopers Hole
Jost Van Dyke
+8 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

Cupecoy Beach with white resort buildings, St. Maarten.
FREE Champagne, Entertainment, Dining & More*
Windstar

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

St. Maarten (Philipsburg)
Sopers Hole
Jost Van Dyke
Virgin Gorda
Gustavia
+2 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Jan 24 - Jan 31, 2026

2 Sailings

Jan 24 - Jan 31, 2026

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.
FREE Champagne, Entertainment, Dining & More*
Windstar

7-night Enchanting Colombia And Panamanian Islands Cruise

Colon (Panama)
San Blas Islands
Cartagena (Colombia)
Santa Marta
Oranjestad

Aboard

Wind Spirit

From

Colon, Panama

1 Sailing

Dec 13, 2025

1 Sailing

Dec 13, 2025

Rocky beach and palm trees in Barbados.
FREE Champagne, Entertainment, Dining & More*
Windstar

7-night Jewels of the Windward Islands Cruise

Bridgetown (Barbados)
Anse Mitan
Castries
Pigeon Island
Bequia
+2 more

Aboard

Wind Surf

From

Bridgetown, Barbados

1 Sailing

Jan 18, 2026

1 Sailing

Jan 18, 2026

Rocky beach and palm trees in Barbados.
FREE Champagne, Entertainment, Dining & More*
Windstar

7-night Windward Island Delights Cruise

Bridgetown (Barbados)
Basseterre
Iles des Saintes
Roseau
Mayreau
+2 more

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Dec 28, 2025

1 Sailing

Dec 28, 2025

Cupecoy Beach with white resort buildings, St. Maarten.
FREE Champagne, Entertainment, Dining & More*
Windstar

7-night Classic Caribbean Cruise

St. Maarten (Philipsburg)
Charlestown
Roseau
Pigeon Island
Iles des Saintes
+2 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

11 Sailings

Dec 7, 2025 - Mar 20, 2027

11 Sailings

Dec 7, 2025 - Mar 20, 2027

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.
FREE Champagne, Entertainment, Dining & More*
Windstar

55-night Star Collector: A Grand Caribbean Adventure Cruise

St. Maarten (Philipsburg)
Falmouth Harbour
Road Bay
Sopers Hole
Jost Van Dyke
+33 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 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.
FREE Champagne, Entertainment, Dining & More*
Windstar

14-night Star Collector: Antilles Adventures Cruise

St. Maarten (Philipsburg)
Basseterre
Little Bay
Gustavia
Deshaies
+8 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 11, 2026

1 Sailing

Jan 11, 2026

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

12-night Star Collector: Ivory Beaches & Sapphire Seas of the Caribbean Cruise

St. Maarten (Philipsburg)
Sopers Hole
Jost Van Dyke
Virgin Gorda
Gustavia
+5 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 2, 2025

1 Sailing

Dec 2, 2025

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

8-night Panama Canal, Cartagena, San Blas Islands & More Cruise

Oranjestad
Cartagena (Colombia)
Bocas del Toro
San Blas Islands
Panama Canal
+2 more

Aboard

Star Pride

From

Oranjestad, Aruba, Caribbean

1 Sailing

Jan 17, 2026

1 Sailing

Jan 17, 2026

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

17-night Star Collector: Hidden Gems of the Caribbean Cruise

St. Maarten (Philipsburg)
Little Bay
Roseau
Castries
Mayreau
+10 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 14, 2026

1 Sailing

Jan 14, 2026

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

St. Maarten (Philipsburg)
Charlestown
Roseau
Pigeon Island
Iles des Saintes
+7 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

19 Sailings

Dec 7, 2025 - Mar 13, 2027

19 Sailings

Dec 7, 2025 - Mar 13, 2027

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

10-night Sublime Southern Caribbean Cruise

Bridgetown (Barbados)
Mayreau
Roseau
Anse Mitan
Deshaies
+6 more

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

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.
FREE Champagne, Entertainment, Dining & More*
Windstar

7-night San Juan & The Virgin Islands Cruise

San Juan
St. George's
Bequia
Mayreau
Iles des Saintes
+2 more

Aboard

Star Pride

From

San Juan, Puerto Rico

7 Sailings

Nov 23, 2025 - Jan 10, 2027

7 Sailings

Nov 23, 2025 - Jan 10, 2027

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.
FREE Champagne, Entertainment, Dining & More*
Windstar

14-night Star Collector: Captivating Caribbean Cruise

Bridgetown (Barbados)
Anse Mitan
Castries
Pigeon Island
Bequia
+8 more

Aboard

Wind Surf

From

Bridgetown, Barbados

1 Sailing

Jan 18, 2026

1 Sailing

Jan 18, 2026

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 Champagne, Entertainment, Dining & More*
Windstar

15-night Star Collector: Merry Christmas & Happy New Years From The Caribbean Cruise

Oranjestad
Willemstad
Kralendijk
St. George's
Mayreau
+7 more

Aboard

Wind Spirit

From

Oranjestad, Aruba, Caribbean

1 Sailing

Dec 20, 2025

1 Sailing

Dec 20, 2025

An aerial view of Anse Mitan in Martinique, a beautiful Caribbean village with a bustling beach, sailboats moored in the bay, and lush green hills in the distance.
FREE Champagne, Entertainment, Dining & More*
Windstar

21-night Star Collector: A Lesser Antilles Odyssey Cruise

St. Maarten (Philipsburg)
Falmouth Harbour
Road Bay
Sopers Hole
Jost Van Dyke
+13 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

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.
FREE Champagne, Entertainment, Dining & More*
Windstar

8-night An ABC Christmas Cruise

Oranjestad
Willemstad
Kralendijk
St. George's
Mayreau
+3 more

Aboard

Wind Spirit

From

Oranjestad, Aruba, Caribbean

1 Sailing

Dec 20, 2025

1 Sailing

Dec 20, 2025

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.
FREE Champagne, Entertainment, Dining & More*
Windstar

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

Balboa
Panama Canal
Bocas del Toro
San Blas Islands
Cartagena (Colombia)
+2 more

Aboard

Star Pride

From

Balboa, Panama

1 Sailing

Jan 11, 2026

1 Sailing

Jan 11, 2026

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 Champagne, Entertainment, Dining & More*
Windstar

7-night Lush & Lovely Islands of the Lesser Antilles Cruise

St. Maarten (Philipsburg)
Basseterre
Little Bay
Gustavia
Deshaies
+3 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 11, 2026

1 Sailing

Jan 11, 2026

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.
FREE Champagne, Entertainment, Dining & More*
Windstar

14-night Star Collector: Lovely Leewards Cruise

San Juan
St. George's
Bequia
Mayreau
Iles des Saintes
+8 more

Aboard

Star Pride

From

San Juan, Puerto Rico

10 Sailings

Nov 23, 2025 - Jan 3, 2027

10 Sailings

Nov 23, 2025 - Jan 3, 2027

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.
FREE Champagne, Entertainment, Dining & More*
Windstar

28-night Star Collector: The Best Of The Windward & Leeward Isles Cruise

St. Maarten (Philipsburg)
Falmouth Harbour
Road Bay
Sopers Hole
Jost Van Dyke
+19 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

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

14-night Star Collector: Lovely Leewards Cruise

San Juan
Cruz Bay
Basseterre
Gustavia
St. Maarten (Philipsburg)
+5 more

Aboard

Star Seeker

From

San Juan, Puerto Rico

7 Sailings

Jan 23 - Mar 6, 2026

7 Sailings

Jan 23 - Mar 6, 2026

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.
FREE Champagne, Entertainment, Dining & More*
Windstar

10-night Blue Waters Of The Leeward Islands Cruise

St. Maarten (Philipsburg)
Little Bay
Roseau
Castries
Mayreau
+5 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 14, 2026

1 Sailing

Jan 14, 2026