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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.

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

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

Overwater bungalows in Tahiti, French Polynesia.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

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

Los Angeles
Papeete
Fakarava
Rangiroa
Taha'a
+4 more

Aboard

Star Breeze

From

Los Angeles, California

9 Sailings

Dec 17, 2025 - Sep 21, 2027

9 Sailings

Dec 17, 2025 - Sep 21, 2027

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

11-night Tahiti & the Tuamotu Islands Cruise

Papeete
Fakarava
Rangiroa
Motu Mahaea
Raiatea
+4 more

Aboard

Star Breeze

From

Papeete, Tahiti, French Polynesia

2 Sailings

Dec 18, 2025 - Apr 30, 2026

2 Sailings

Dec 18, 2025 - Apr 30, 2026

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

18-night Star Collector – Twice the Tahiti Cruise

Papeete
Moorea
Raiatea
Motu Mahaea
Bora Bora
+4 more

Aboard

Star Breeze

From

Papeete, Tahiti, French Polynesia

5 Sailings

Dec 11, 2025 - Dec 10, 2026

5 Sailings

Dec 11, 2025 - Dec 10, 2026

Gondolas on a canal in Venice.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Windstar

8-night Winter Italy And The Dalmatian Coast Cruise

Rome (Civitavecchia)
Naples
Strait of Messina
Dubrovnik
Zadar
+2 more

Aboard

Star Legend

From

Civitavecchia, Rome, Italy

3 Sailings

Dec 27, 2025 - Mar 15, 2026

3 Sailings

Dec 27, 2025 - Mar 15, 2026

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

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

A beautiful image of a narrow, stone-paved street in a medieval Italian village near Livorno, adorned with ivy-covered walls, potted plants, and colorful flowers, giving a feeling of tranquility.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

7-night Europe's Winter Riviera Cruise

Barcelona
Nice
Genoa
Florence/Pisa (Livorno)
Rome (Civitavecchia)

Aboard

Star Legend

From

Barcelona, Spain

3 Sailings

Dec 20, 2025 - Mar 25, 2027

3 Sailings

Dec 20, 2025 - Mar 25, 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 dramatic sunset over Lake Arenal in Costa Rica, with a majestic, conical Arenal Volcano emitting a plume of smoke and fiery clouds into the orange sky.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

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

San Jose (C.R.)
Arenal
Monteverde
Puerto Caldera (Puntarenas)
Golfo Dulce (Puerto Jimenez)
+6 more

Aboard

Star Pride

From

San Jose, Costa Rica

3 Sailings

Dec 16, 2025 - Feb 26, 2026

3 Sailings

Dec 16, 2025 - Feb 26, 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 wide-angle view of the bustling harbor of Messina in Sicily, Italy, with the iconic gold statue of the Madonna della Lettera on a monument overlooking the Strait of Messina.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

15-night Star Collector: Winter In Europe's Rivieras & Croatia Cruise

Barcelona
Nice
Genoa
Florence/Pisa (Livorno)
Rome (Civitavecchia)
+6 more

Aboard

Star Legend

From

Barcelona, Spain

2 Sailings

Dec 20, 2025 - Jan 28, 2026

2 Sailings

Dec 20, 2025 - Jan 28, 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 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 All-Inclusive Package Upgrade*+ 1 more offer
Windstar

8-night Naturally Costa Rica Cruise

Puerto Caldera (Puntarenas)
Playa Flamingo
Curu (Reserve)
Punta Leona
Quepos
+4 more

Aboard

Star Pride

From

Puerto Caldera, Costa Rica

1 Sailing

Jan 3, 2026

1 Sailing

Jan 3, 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

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 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 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 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 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

A breathtaking landscape of Raiatea Island, French Polynesia, showcasing lush, green volcanic mountains covered in tropical foliage descending into a tranquil turquoise lagoon.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

10-night Tahiti & Moorea Culture Through Cuisine Cruise/Land Package

Papeete
Moorea
Bora Bora
Motu Mahaea
Raiatea

Aboard

Star Breeze

From

Papeete, Tahiti, French Polynesia

3 Sailings

Dec 4, 2025 - May 28, 2026

3 Sailings

Dec 4, 2025 - May 28, 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

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 breathtaking landscape of Raiatea Island, French Polynesia, showcasing lush, green volcanic mountains covered in tropical foliage descending into a tranquil turquoise lagoon.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

10-night Overwater Bungalow & Tahitian Paradises Cruise/Land Package

Papeete
Moorea
Raiatea
Taha'a
Bora Bora

Aboard

Star Breeze

From

Papeete, Tahiti, French Polynesia

17 Sailings

Nov 27, 2025 - Dec 10, 2026

17 Sailings

Nov 27, 2025 - Dec 10, 2026

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