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

20-night Star Collector: Central America & The Caribbean: Cloudforest Coastlines, Canal Locks & Calypso Concerts Cruise

San Juan
Cruz Bay
Gustavia
Basseterre
St. Maarten (Philipsburg)
+13 more

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 30, 2025

1 Sailing

Nov 30, 2025

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

*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.

Alcazaba fortress in Malaga.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

7-night Southern Spain Winter Escapes Cruise

Barcelona
Palma de Mallorca
Valencia
Cartagena (Spain)
Gibraltar

Aboard

Star Legend

From

Barcelona, Spain

2 Sailings

Nov 7 - Nov 21, 2025

2 Sailings

Nov 7 - Nov 21, 2025

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

13-night Star Collector: Beaches & Bastions Of The BVI And Spanish Caribbean Cruise

San Juan
Cruz Bay
Gustavia
Basseterre
St. Maarten (Philipsburg)
+7 more

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 30, 2025

1 Sailing

Nov 30, 2025

Anaga Mountains landscape, Tenerife.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

10-night Canary Island Idyll Cruise

Santa Cruz de Tenerife
La Gomera
Santa Cruz de La Palma
Funchal (Madeira)
Lanzarote
+2 more

Aboard

Wind Star

From

Santa Cruz de Tenerife, Canary Islands

10 Sailings

Nov 20, 2025 - Feb 18, 2026

10 Sailings

Nov 20, 2025 - Feb 18, 2026

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

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

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

Plaza Espana in Barcelona, showcasing unique architectural design and vibrant surroundings.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

7-night Southern Spain Winter Escapes Cruise

Malaga
Gibraltar
Cartagena (Spain)
Valencia
Palma de Mallorca

Aboard

Star Legend

From

Malaga, Spain

2 Sailings

Nov 14 - Dec 13, 2025

2 Sailings

Nov 14 - Dec 13, 2025

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

A picturesque view of a brick lighthouse perched on the lush, green cliffs of Maroe Bay, Huahine, with the ocean and a blue sky in the background.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

10-night Tahiti & The Tuamotu Islands Cruise

Papeete
Fakarava
Rangiroa
Motu Mahaea
Bora Bora
+3 more

Aboard

Star Breeze

From

Papeete, Tahiti, French Polynesia

10 Sailings

Nov 10, 2025 - Sep 23, 2027

10 Sailings

Nov 10, 2025 - Sep 23, 2027

A stunning view of Santa Cruz de la Palma's black sand beach, with gentle waves from the Atlantic Ocean, a colorful town, and green, volcanic mountains in the background.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

8-night Colorful Canary Islands Cruise

Lisbon
Funchal (Madeira)
Santa Cruz de La Palma
La Gomera
Las Palmas (Gran Canaria)
+2 more

Aboard

Wind Star

From

Lisbon, Portugal

1 Sailing

Nov 12, 2025

1 Sailing

Nov 12, 2025

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

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 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

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 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 All-Inclusive Package Upgrade*+ 1 more offer
Windstar

7-night San Juan & The Virgin Islands Cruise

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

Aboard

Star Pride

From

San Juan, Puerto Rico

9 Sailings

Nov 9, 2025 - Jan 10, 2027

9 Sailings

Nov 9, 2025 - Jan 10, 2027

A scenic view of Moorea, French Polynesia, with turquoise lagoons, a row of luxurious overwater bungalows, lush palm trees along the coast, and a distant island under a stunning blue sky.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

7-night Dreams of Tahiti Cruise

Papeete
Moorea
Raiatea
Taha'a
Bora Bora

Aboard

Star Breeze

From

Papeete, Tahiti, French Polynesia

13 Sailings

Nov 20, 2025 - May 28, 2026

13 Sailings

Nov 20, 2025 - May 28, 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 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 All-Inclusive Package Upgrade*+ 1 more offer
Windstar

14-night Star Collector: Lovely Leewards Cruise

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

Aboard

Star Pride

From

San Juan, Puerto Rico

12 Sailings

Nov 9, 2025 - Jan 3, 2027

12 Sailings

Nov 9, 2025 - Jan 3, 2027

A scenic view of Moorea, French Polynesia, with turquoise lagoons, a row of luxurious overwater bungalows, lush palm trees along the coast, and a distant island under a stunning blue sky.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

17-night Star Collector – Twice the Tahiti Cruise

Papeete
Fakarava
Rangiroa
Motu Mahaea
Bora Bora
+4 more

Aboard

Star Breeze

From

Papeete, Tahiti, French Polynesia

4 Sailings

Nov 10, 2025 - Nov 23, 2026

4 Sailings

Nov 10, 2025 - Nov 23, 2026

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 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