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*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.

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

18-night Star Collector: Reefs & Rainforests: The Caribbean, Colombia, Panama & Costa Rica via the Panama Canal Cruise

Bridgetown (Barbados)
Bequia
Mayreau
St. George's
Kralendijk
+11 more

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Nov 18, 2025

1 Sailing

Nov 18, 2025

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

25-night Star Collector: Southern Caribbean Thanksgiving Jubilee Cruise

Lisbon
Bridgetown (Barbados)
Bequia
Mayreau
St. George's
+6 more

Aboard

Wind Spirit

From

Lisbon, Portugal

1 Sailing

Nov 4, 2025

1 Sailing

Nov 4, 2025

Rocky beach and palm trees in Barbados.
FREE All-Inclusive Package Upgrade*+ 1 more offer
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 All-Inclusive Package Upgrade*+ 1 more offer
Windstar

14-night Star Collector: Captivating Caribbean Cruise

Bridgetown (Barbados)
Little Bay
Iles des Saintes
Roseau
Anse Mitan
+8 more

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 7, 2026

1 Sailing

Mar 7, 2026

Colorful colonial balconies in Cartagena.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

17-night Star Collector: Seeking The Antilles Cruise

San Juan
Cruz Bay
St. John's
Iles des Saintes
Pigeon Island
+10 more

Aboard

Star Seeker

From

San Juan, Puerto Rico

1 Sailing

Mar 27, 2026

1 Sailing

Mar 27, 2026

Blue Mosque and historic Istanbul skyline with Bosphorus Strait.
FREE Champagne, Entertainment, Dining & More*
Windstar

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

Istanbul
Myrina
Mykonos
Kusadasi (Ephesus)
Bodrum
+43 more

Aboard

Star Legend

From

Istanbul, Turkey

1 Sailing

Oct 19, 2026

1 Sailing

Oct 19, 2026

An aerial view of the Kralendijk waterfront in Bonaire, showcasing the contrast between the deep blue ocean and the shallow turquoise water near the shore, with sailboats anchored offshore.
FREE Champagne, Entertainment, Dining & More*
Windstar

25-night Star Collector: Southern Caribbean Thanksgiving Jubilee Cruise

Lisbon
Bridgetown (Barbados)
Bequia
St. George's
Kralendijk
+6 more

Aboard

Wind Star

From

Lisbon, Portugal

1 Sailing

Nov 10, 2026

1 Sailing

Nov 10, 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 All-Inclusive Package Upgrade*+ 1 more offer
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

A close-up of a small, adorable squirrel monkey with a black cap and a light brown body, perched on a tree branch surrounded by lush, yellow-green leaves.
FREE Champagne, Entertainment, Dining & More*
Windstar

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

Bridgetown (Barbados)
Bequia
St. George's
Kralendijk
Willemstad
+11 more

Aboard

Wind Star

From

Bridgetown, Barbados

1 Sailing

Nov 24, 2026

1 Sailing

Nov 24, 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 All-Inclusive Package Upgrade*+ 1 more offer
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

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

11-night Colombian & Southern Caribbean Coastlines Cruise

Bridgetown (Barbados)
Bequia
St. George's
Kralendijk
Willemstad
+5 more

Aboard

Wind Star

From

Bridgetown, Barbados

1 Sailing

Nov 24, 2026

1 Sailing

Nov 24, 2026

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 All-Inclusive Package Upgrade*+ 1 more offer
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 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 Package Upgrade*+ 1 more offer
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 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 All-Inclusive Package Upgrade*+ 1 more offer
Windstar

11-night Columbian & Southern Caribbean Coastlines Cruise

Bridgetown (Barbados)
Bequia
Mayreau
St. George's
Kralendijk
+5 more

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Nov 18, 2025

1 Sailing

Nov 18, 2025

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 All-Inclusive Package Upgrade*+ 1 more offer
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 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 Package Upgrade*+ 1 more offer
Windstar

10-night Gems Of The Leeward Islands Cruise

San Juan
Cruz Bay
St. John's
Iles des Saintes
Pigeon Island
+5 more

Aboard

Star Seeker

From

San Juan, Puerto Rico

1 Sailing

Mar 27, 2026

1 Sailing

Mar 27, 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 All-Inclusive Package Upgrade*+ 1 more offer
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

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 All-Inclusive Package Upgrade*+ 1 more offer
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

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 All-Inclusive Package Upgrade*+ 1 more offer
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 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 Package Upgrade*+ 1 more offer
Windstar

24-night Star Collector: Historic Caribbean: Legendary Islands, Colombia And Panama Cruise

San Juan
Cruz Bay
St. John's
Iles des Saintes
Pigeon Island
+16 more

Aboard

Star Seeker

From

San Juan, Puerto Rico

1 Sailing

Mar 27, 2026

1 Sailing

Mar 27, 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 All-Inclusive Package Upgrade*+ 1 more offer
Windstar

14-night Star Collector: Lovely Leewards Cruise

San Juan
Cruz Bay
Basseterre
Gustavia
St. Maarten (Philipsburg)
+8 more

Aboard

Star Pride

From

San Juan, Puerto Rico

13 Sailings

Nov 2, 2025 - Jan 3, 2027

13 Sailings

Nov 2, 2025 - Jan 3, 2027

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 Package Upgrade*+ 1 more offer
Windstar

49-night Star Collector: Grand Caribbean & Americas Explorer Cruise

San Juan
Cruz Bay
St. John's
Iles des Saintes
Pigeon Island
+30 more

Aboard

Star Seeker

From

San Juan, Puerto Rico

1 Sailing

Mar 27, 2026

1 Sailing

Mar 27, 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

11-night Gems Of The Leeward Islands Cruise

San Juan
Cruz Bay
Gustavia
Basseterre
Falmouth Harbour
+6 more

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Oct 28, 2026

1 Sailing

Oct 28, 2026

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.
FREE Champagne, Entertainment, Dining & More*
Windstar

7-night Windward Islands Surf & Sunsets Cruise

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

Aboard

Star Pride

From

San Juan, Puerto Rico

5 Sailings

Nov 8, 2026 - Jan 3, 2027

5 Sailings

Nov 8, 2026 - 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 All-Inclusive Package Upgrade*+ 1 more offer
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