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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

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 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

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

Immaculate Conception Cathedral in Colon.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

7-night Costa Rica & Panama Canal Cruise

Colon (Panama)
Panama Canal
Balboa
Isla Parida
Golfo Dulce (Puerto Jimenez)
+3 more

Aboard

Wind Spirit

From

Colon, Panama

1 Sailing

Nov 29, 2025

1 Sailing

Nov 29, 2025

Cupecoy Beach with white resort buildings, St. Maarten.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

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

St. Maarten (Philipsburg)
St. John's
Road Bay
Sopers Hole
Jost Van Dyke
+2 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Feb 14 - Feb 21, 2026

2 Sailings

Feb 14 - Feb 21, 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

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

Cupecoy Beach with white resort buildings, St. Maarten.
FREE All-Inclusive Package Upgrade*+ 1 more offer
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

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

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

St. Maarten (Philipsburg)
Sopers Hole
Jost Van Dyke
Virgin Gorda
Gustavia
+8 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 21, 2026

1 Sailing

Feb 21, 2026

Belém Tower on Tagus River.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

14-night Ocean Crossings Cruise

Lisbon
Bridgetown (Barbados)

Aboard

Wind Spirit

From

Lisbon, Portugal

1 Sailing

Nov 4, 2025

1 Sailing

Nov 4, 2025

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

22-night Star Collector: A Lesser Antilles Odyssey Cruise

St. Maarten (Philipsburg)
St. John's
Road Bay
Virgin Gorda
Sopers Hole
+9 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 21, 2026

1 Sailing

Feb 21, 2026

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

7-night Jewels of the Windward Islands Cruise

Bridgetown (Barbados)
Basseterre
St. John's
Iles des Saintes
Roseau
+3 more

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 7, 2026

1 Sailing

Mar 7, 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

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

14-night Star Collector: Caribbean Explorations Cruise

St. Maarten (Philipsburg)
Sopers Hole
Jost Van Dyke
Virgin Gorda
Gustavia
+7 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Jan 31 - Feb 7, 2026

2 Sailings

Jan 31 - Feb 7, 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

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

St. Maarten (Philipsburg)
Basseterre
Gustavia
Little Bay
Iles des Saintes
+3 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 28, 2026

1 Sailing

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

7-night Classic Caribbean Cruise

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

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 7, 2026

1 Sailing

Feb 7, 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

28-night Star Collector: Grand Caribbean & Panamanian Adventure Cruise

St. Maarten (Philipsburg)
St. John's
Road Bay
Virgin Gorda
Sopers Hole
+14 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 21, 2026

1 Sailing

Feb 21, 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

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

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

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 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 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 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

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

7-night Costa Rica & Panama Canal Cruise

Puerto Caldera (Puntarenas)
Quepos
Golfo Dulce (Puerto Jimenez)
Isla Parida
Balboa
+3 more

Aboard

Wind Spirit

From

Puerto Caldera, Costa Rica

1 Sailing

Dec 6, 2025

1 Sailing

Dec 6, 2025

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

15-night Star Collector: Antilles Adventure Cruise

St. Maarten (Philipsburg)
Basseterre
Gustavia
St. John's
Iles des Saintes
+5 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 28, 2026

1 Sailing

Feb 28, 2026

A cruise ship navigating through the Gatun Locks of the Panama Canal, an important navigational route and popular tourist destination.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

11-night Monteverde Cloud Forest & Arenal Volcano Cruise/Land Package

Colon (Panama)
Panama Canal
Balboa
Isla Parida
Golfo Dulce (Puerto Jimenez)
+5 more

Aboard

Wind Spirit

From

Colon, Panama

1 Sailing

Nov 29, 2025

1 Sailing

Nov 29, 2025