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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.

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

8-night Winter Italy And The Dalmatian Coast Cruise

Venice
Zadar
Dubrovnik
Strait of Messina
Naples
+2 more

Aboard

Star Legend

From

Venice, Italy

3 Sailings

Jan 4 - Mar 23, 2026

3 Sailings

Jan 4 - Mar 23, 2026

Plaza Espana in Barcelona, showcasing unique architectural design and vibrant surroundings.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Windstar

16-night Star Collector: Winter In Spain And The Rivieras Cruise

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

Aboard

Star Legend

From

Civitavecchia, Rome, Italy

2 Sailings

Jan 12 - Feb 20, 2026

2 Sailings

Jan 12 - Feb 20, 2026

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.
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

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

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

Plaza Espana in Barcelona, showcasing unique architectural design and vibrant surroundings.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Windstar

12-night Winter Riviera & Madrid Cruise/Land Package

Rome (Civitavecchia)
Florence/Pisa (Livorno)
Genoa
Nice
Barcelona
+2 more

Aboard

Star Legend

From

Civitavecchia, Rome, Italy

2 Sailings

Jan 12 - Feb 20, 2026

2 Sailings

Jan 12 - Feb 20, 2026

Promenade des Anglais and beach in Nice.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Windstar

7-night Europe's Winter Riviera Cruise

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

Aboard

Star Legend

From

Civitavecchia, Rome, Italy

3 Sailings

Jan 12, 2026 - Nov 5, 2027

3 Sailings

Jan 12, 2026 - Nov 5, 2027

Promenade des Anglais and beach in Nice.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

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

Venice
Zadar
Dubrovnik
Strait of Messina
Naples
+6 more

Aboard

Star Legend

From

Venice, Italy

2 Sailings

Jan 4 - Feb 12, 2026

2 Sailings

Jan 4 - Feb 12, 2026

Alcazaba fortress in Malaga.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

24-night Star Collector: Winter Mediterranean Adventure Cruise

Venice
Zadar
Dubrovnik
Strait of Messina
Naples
+11 more

Aboard

Star Legend

From

Venice, Italy

2 Sailings

Jan 4 - Feb 12, 2026

2 Sailings

Jan 4 - Feb 12, 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

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 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 low-angle shot of the magnificent Palacio Consistorial, the town hall of Cartagena, Spain, showcasing its ornate, white marble facade and domed rooftops against a blue sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

9-night Southern Spain Winter Escapes Cruise

Barcelona
Valencia
Cartagena (Spain)
Gibraltar
Malaga
+2 more

Aboard

Star Legend

From

Barcelona, Spain

2 Sailings

Jan 19 - Feb 27, 2026

2 Sailings

Jan 19 - Feb 27, 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

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

14-night Star Collector: Winter In Spain And The Rivieras Cruise

Malaga
Gibraltar
Cartagena (Spain)
Valencia
Palma de Mallorca
+5 more

Aboard

Star Legend

From

Malaga, Spain

1 Sailing

Dec 13, 2025

1 Sailing

Dec 13, 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 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

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

22-night Star Collector: Winter Mediterranean Adventure Cruise

Malaga
Gibraltar
Cartagena (Spain)
Valencia
Palma de Mallorca
+11 more

Aboard

Star Legend

From

Malaga, Spain

1 Sailing

Dec 13, 2025

1 Sailing

Dec 13, 2025

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 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

An underwater scene near Freeport, Bahamas, with two colorful striped fish swimming above a collection of starfish on the sandy ocean floor amidst coral reefs.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

16-night Star Seeker Maiden Voyage

Malaga
Santa Cruz de Tenerife
Freeport
Miami

Aboard

Star Seeker

From

Malaga, Spain

1 Sailing

Dec 28, 2025

1 Sailing

Dec 28, 2025

A striking low-angle shot of a classic Art Nouveau building, the Estación del Norte train station in Valencia, Spain, featuring intricate carvings and a blue-tiled dome against a bright blue sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

24-night Star Collector: Winter Mediterranean Adventure Cruise

Barcelona
Valencia
Cartagena (Spain)
Gibraltar
Malaga
+11 more

Aboard

Star Legend

From

Barcelona, Spain

1 Sailing

Jan 19, 2026

1 Sailing

Jan 19, 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

16-night Star Collector: Winter In Spain And The Rivieras Cruise

Barcelona
Valencia
Cartagena (Spain)
Gibraltar
Malaga
+6 more

Aboard

Star Legend

From

Barcelona, Spain

1 Sailing

Jan 19, 2026

1 Sailing

Jan 19, 2026