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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.

St. Peter's Basilica, Rome cityscape at sunset.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Windstar

7-night Yachtsman's Harbors of the Rivieras Cruise

Rome (Civitavecchia)
Portoferraio
Portofino
Monte Carlo
Cannes
+3 more

Aboard

Wind Surf

From

Civitavecchia, Rome, Italy

1 Sailing

Nov 3, 2025

1 Sailing

Nov 3, 2025

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

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

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

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

8-night In the Wake of the Spanish Armadas Cruise

Oranjestad
Santa Marta
Cartagena (Colombia)
Bocas del Toro
Colon (Panama)

Aboard

Wind Surf

From

Oranjestad, Aruba, Caribbean

1 Sailing

Feb 1, 2026

1 Sailing

Feb 1, 2026

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

15-night Star Collector: Windward Islands & Spanish New World Cruise

Bridgetown (Barbados)
Man O'War Bay
Mayreau
Soufriere
Kralendijk
+7 more

Aboard

Wind Surf

From

Bridgetown, Barbados

1 Sailing

Jan 25, 2026

1 Sailing

Jan 25, 2026

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

The ancient stone ruins of a majestic Mayan temple or pyramid, featuring historic architecture at an archaeological site in Mexico's Costa Maya region.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

8-night Mayan Legacies Cruise

Colon (Panama)
Bocas del Toro
San Andres Island
Roatan Island
Belize City
+3 more

Aboard

Wind Surf

From

Colon, Panama

1 Sailing

Feb 9, 2026

1 Sailing

Feb 9, 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

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 scenic panoramic shot from the top of the Rock of Gibraltar, overlooking the city, marina, and the Mediterranean Sea under a bright blue sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

8-night Spanish Symphony Cruise

Barcelona
Palma de Mallorca
Cartagena (Spain)
Almeria
Malaga
+4 more

Aboard

Wind Surf

From

Barcelona, Spain

3 Sailings

Nov 10, 2025 - Oct 30, 2026

3 Sailings

Nov 10, 2025 - Oct 30, 2026

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

11-night Stars of the Greater Antilles Cruise

Cozumel
Grand Cayman (George Town)
Cayman Brac
Port Antonio
Santo Domingo
+5 more

Aboard

Wind Surf

From

Cozumel, Mexico

1 Sailing

Feb 17, 2026

1 Sailing

Feb 17, 2026

A captivating half-underwater, half-above-water shot of a person snorkeling in the vibrant turquoise waters of the British Virgin Islands with stunning rock formations and palm trees visible above the waterline.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

5-night Barefoot Break in the British Virgin Islands Cruise

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

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 2, 2025

1 Sailing

Dec 2, 2025

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

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 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

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 panoramic sunset shot of the beautiful harbor in Palma de Mallorca, Spain, with a marina full of boats and buildings on the surrounding hills.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Windstar

15-night Star Collector – Enchantment of the Western Mediterranean Cruise

Rome (Civitavecchia)
Portoferraio
Portofino
Monte Carlo
Cannes
+11 more

Aboard

Wind Surf

From

Civitavecchia, Rome, Italy

1 Sailing

Nov 3, 2025

1 Sailing

Nov 3, 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

14-night Ocean Crossings Cruise

Lisbon
St. John's
St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Lisbon, Portugal

2 Sailings

Nov 18, 2025 - Dec 5, 2026

2 Sailings

Nov 18, 2025 - Dec 5, 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

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

St. Maarten (Philipsburg)
Falmouth Harbour
Road Bay
Sopers Hole
Jost Van Dyke
+2 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

4 Sailings

Dec 14, 2025 - Mar 28, 2026

4 Sailings

Dec 14, 2025 - Mar 28, 2026

A captivating half-underwater, half-above-water shot of a person snorkeling in the vibrant turquoise waters of the British Virgin Islands with stunning rock formations and palm trees visible above the waterline.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

19-night Star Collector: Hearty Ports & Rum Punches - A Trans-Atlantic Crossing Cruise

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

Aboard

Wind Surf

From

Lisbon, Portugal

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 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

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

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 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

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

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

16-night Star Collector: Natural History Meets Ancient Mystery: Latin America & Beyond Cruise

Oranjestad
Santa Marta
Cartagena (Colombia)
Bocas del Toro
Colon (Panama)
+6 more

Aboard

Wind Surf

From

Oranjestad, Aruba, Caribbean

1 Sailing

Feb 1, 2026

1 Sailing

Feb 1, 2026

A close-up aerial view of the dramatic limestone bluff, known as the "Bluff," a landmark on Cayman Brac island, with waves crashing against its vertical face.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

19-night Star Collector: Caribbean Cultures: Latin America & the Greater Antilles Cruise

Colon (Panama)
Bocas del Toro
San Andres Island
Roatan Island
Belize City
+11 more

Aboard

Wind Surf

From

Colon, Panama

1 Sailing

Feb 9, 2026

1 Sailing

Feb 9, 2026