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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

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

Plaza Mayor in Madrid, Spain.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

12-night Spanish Symphony & Madrid Medley Cruise/Land Package

Madrid
Segovia
Barcelona
Palma de Mallorca
Cartagena (Spain)
+6 more

Aboard

Wind Surf

From

Madrid, Spain

2 Sailings

Nov 6, 2025 - Oct 26, 2026

2 Sailings

Nov 6, 2025 - Oct 26, 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

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

Belém Tower on Tagus River.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

12-night Portuguese Passages & Spanish Shorelines Cruise/Land Package

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

Aboard

Wind Surf

From

Barcelona, Spain

1 Sailing

Nov 10, 2025

1 Sailing

Nov 10, 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

Overwater bungalows in Tahiti, French Polynesia.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

11-night Golden Days In Bora Bora Cruise/Land Package

Papeete
Moorea
Raiatea
Motu Mahaea
Bora Bora

Aboard

Star Breeze

From

Papeete, Tahiti, French Polynesia

2 Sailings

Nov 19 - Nov 26, 2025

2 Sailings

Nov 19 - Nov 26, 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

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

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*+ 2 more offers
TCW EXCLUSIVE
Windstar

18-night Star Collector – Southern Spain and Canary Islands Cruise

Barcelona
Barcelona (Tarragona)
Palma de Mallorca
Valencia
Cartagena (Spain)
+9 more

Aboard

Wind Star

From

Barcelona, Spain

1 Sailing

Nov 2, 2025

1 Sailing

Nov 2, 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

A picturesque view of the historic Cape Spartel Lighthouse on a cliff overlooking the Atlantic Ocean near Tangier, Morocco.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

10-night Treasures of Southern Spain and Morocco Cruise

Barcelona
Barcelona (Tarragona)
Palma de Mallorca
Valencia
Cartagena (Spain)
+4 more

Aboard

Wind Star

From

Barcelona, Spain

1 Sailing

Nov 2, 2025

1 Sailing

Nov 2, 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 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

10-night Golden Days In Bora Bora Cruise/Land Package

Papeete
Bora Bora
Moorea
Raiatea
Motu Mahaea

Aboard

Star Breeze

From

Papeete, Tahiti, French Polynesia

4 Sailings

Nov 17 - Dec 8, 2025

4 Sailings

Nov 17 - Dec 8, 2025

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

An aerial panoramic shot of the stunning coast of Palamós, Spain, with a beautiful beach, clear turquoise water, and houses built on the hillside.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Windstar

12-night Yachtsman’s Mediterranean Rivieras & Madrid Cruise/Land Package

Rome (Civitavecchia)
Portoferraio
Portofino
Monte Carlo
Cannes
+5 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 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 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 Final Rose & Overwater Bungalows Cruise/Land Package

Papeete
Moorea
Raiatea
Motu Mahaea
Bora Bora

Aboard

Star Breeze

From

Papeete, Tahiti, French Polynesia

4 Sailings

Nov 17 - Dec 8, 2025

4 Sailings

Nov 17 - Dec 8, 2025

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

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

7-night San Juan & The Virgin Islands Cruise

San Juan
Cruz Bay
Basseterre
Gustavia
St. Maarten (Philipsburg)
+2 more

Aboard

Star Pride

From

San Juan, Puerto Rico

10 Sailings

Nov 2, 2025 - Jan 10, 2027

10 Sailings

Nov 2, 2025 - Jan 10, 2027

A serene tropical beach on Fakarava atoll in French Polynesia, featuring a white sandy shoreline fringed with swaying palm trees and clear turquoise waters under a sunny blue sky.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

11-night Tahiti & The Tuamotu Islands Cruise/Land Package

Papeete
Fakarava
Rangiroa
Motu Mahaea
Bora Bora
+3 more

Aboard

Star Breeze

From

Papeete, Tahiti, French Polynesia

1 Sailing

Nov 9, 2025

1 Sailing

Nov 9, 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

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 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