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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.

Historic cityscape of Porto, Portugal, along the Douro River at dusk.
Windstar

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

Lisbon
Fatima
Porto (Oporto)
Douro Valley
Coimbra
+8 more

Aboard

Wind Surf

From

Lisbon, Portugal

2 Sailings

Apr 14, 2026 - Apr 7, 2027

2 Sailings

Apr 14, 2026 - Apr 7, 2027

Plaza Mayor in Madrid, Spain.
FREE Champagne, Entertainment, Dining & More*
Windstar

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

Lisbon
Seville (Cadiz)
Gibraltar
Malaga
Almeria
+6 more

Aboard

Wind Surf

From

Lisbon, Portugal

2 Sailings

Apr 18 - Jun 22, 2026

2 Sailings

Apr 18 - Jun 22, 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

Plaza Espana in Barcelona, showcasing unique architectural design and vibrant surroundings.
FREE Champagne, Entertainment, Dining & More*
Windstar

14-night Next Stop Madrid: Spanish Treasures Cruise/Land Package

Lisbon
Tangier
Malaga
Cartagena (Spain)
Valencia
+6 more

Aboard

Wind Star

From

Lisbon, Portugal

1 Sailing

Apr 7, 2026

1 Sailing

Apr 7, 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

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

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

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

13-night Madrid & Southern Spain Winter Escapes Cruise/Land Package

Madrid
Segovia
Barcelona
Valencia
Cartagena (Spain)
+4 more

Aboard

Star Legend

From

Madrid, Spain

1 Sailing

Feb 23, 2026

1 Sailing

Feb 23, 2026

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

25-night Star Collector: Classic Crossing To Spain & More Cruise

Bridgetown (Barbados)
Lisbon
Tangier
Malaga
Cartagena (Spain)
+5 more

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 28, 2026

1 Sailing

Mar 28, 2026

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 picturesque view of the historic Cape Spartel Lighthouse on a cliff overlooking the Atlantic Ocean near Tangier, Morocco.
FREE Champagne, Entertainment, Dining & More*
Windstar

10-night Treasures of Southern Spain & Morocco Cruise

Lisbon
Tangier
Malaga
Cartagena (Spain)
Valencia
+4 more

Aboard

Wind Spirit

From

Lisbon, Portugal

1 Sailing

Apr 12, 2026

1 Sailing

Apr 12, 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 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 panoramic sunset shot of the beautiful harbor in Palma de Mallorca, Spain, with a marina full of boats and buildings on the surrounding hills.
FREE Champagne, Entertainment, Dining & More*
Windstar

17-night Star Collector: Romance Of The West Med Cruise

Lisbon
Tangier
Malaga
Cartagena (Spain)
Valencia
+9 more

Aboard

Wind Star

From

Lisbon, Portugal

1 Sailing

Apr 7, 2026

1 Sailing

Apr 7, 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.
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 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 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

A historic fortress, the Castle of La Calahorra, stands on a hilltop overlooking a town with white-washed houses below, under a blue sky with scattered clouds in Almería, Spain.
FREE Champagne, Entertainment, Dining & More*
Windstar

22-night Star Collector: Atlantic Interludes & Iberian Indulgences Cruise

St. Maarten (Philipsburg)
Ponta Delgada (Azores)
Lisbon
Seville (Cadiz)
Gibraltar
+6 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Apr 4, 2026

1 Sailing

Apr 4, 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

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

Plaza Mayor in Madrid, Spain.
FREE Champagne, Entertainment, Dining & More*
Windstar

14-night Next Stop Madrid: Spanish Treasures Cruise/Land Package

Lisbon
Tangier
Malaga
Cartagena (Spain)
Valencia
+6 more

Aboard

Wind Spirit

From

Lisbon, Portugal

1 Sailing

Apr 12, 2026

1 Sailing

Apr 12, 2026

A picturesque view of the historic Cape Spartel Lighthouse on a cliff overlooking the Atlantic Ocean near Tangier, Morocco.
FREE Champagne, Entertainment, Dining & More*
Windstar

10-night Treasures Of Southern Spain & Morocco Cruise

Lisbon
Tangier
Malaga
Cartagena (Spain)
Valencia
+4 more

Aboard

Wind Star

From

Lisbon, Portugal

1 Sailing

Apr 7, 2026

1 Sailing

Apr 7, 2026