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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.

Promenade des Anglais and beach in Nice.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

11-night Winter Riviera & Madrid Cruise/Land Package

Aboard

Star Legend

From

Madrid, Spain

1 Sailing

Jan 24, 2026

1 Sailing

Jan 24, 2026

Alcazaba fortress in Malaga.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

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

Cartagena (Spain)

Aboard

Star Legend

From

Madrid, Spain

1 Sailing

Feb 23, 2026

1 Sailing

Feb 23, 2026

Plaza Espana in Barcelona, showcasing unique architectural design and vibrant surroundings.

Up to $500 FREE Onboard Credit*+ 3 more offers

Windstar

12-night Winter Riviera & Madrid Cruise/Land Package

Rome (Civitavecchia)

Florence/Pisa (Livorno)

Aboard

Star Legend

From

Civitavecchia, Rome, Italy

2 Sailings

Jan 12 - Feb 20, 2026

2 Sailings

Jan 12 - Feb 20, 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

Cartagena (Spain)

Aboard

Wind Star

From

Lisbon, Portugal

1 Sailing

Apr 7, 2026

1 Sailing

Apr 7, 2026

St. Peter's Basilica, Rome cityscape at sunset.

FREE Champagne, Entertainment, Dining & More*

Windstar

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

Aboard

Star Legend

From

Madrid, Spain

1 Sailing

Sep 7, 2026

1 Sailing

Sep 7, 2026

Plaza Mayor in Madrid, Spain.

FREE Champagne, Entertainment, Dining & More*

Windstar

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

Aboard

Wind Surf

From

Madrid, Spain

1 Sailing

Jun 26, 2026

1 Sailing

Jun 26, 2026

Plaza Mayor in Madrid, Spain.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

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

Palma de Mallorca

Cartagena (Spain)

Aboard

Wind Surf

From

Madrid, Spain

2 Sailings

Nov 6, 2025 - Oct 26, 2026

2 Sailings

Nov 6, 2025 - Oct 26, 2026

Plaza Mayor in Madrid, Spain.

FREE Champagne, Entertainment, Dining & More*

Windstar

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

Cartagena (Spain)

Aboard

Wind Spirit

From

Lisbon, Portugal

1 Sailing

Apr 12, 2026

1 Sailing

Apr 12, 2026

Plaza Mayor in Madrid, Spain.

FREE Champagne, Entertainment, Dining & More*

Windstar

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

Aboard

Wind Surf

From

Madrid, Spain

1 Sailing

Apr 22, 2026

1 Sailing

Apr 22, 2026

Plaza Mayor in Madrid, Spain.

FREE Champagne, Entertainment, Dining & More*

Windstar

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

Seville (Cadiz)

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 Champagne, Entertainment, Dining & More*

Windstar

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

Barcelona (Tarragona)

Palma de Mallorca

Aboard

Wind Spirit

From

Madrid, Spain

1 Sailing

Oct 26, 2026

1 Sailing

Oct 26, 2026

Plaza Mayor in Madrid, Spain.

Up to $500 FREE Onboard Credit*+ 1 more offer

Windstar

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

Rome (Civitavecchia)

Aboard

Wind Surf

From

Civitavecchia, Rome, Italy

1 Sailing

Oct 25, 2026

1 Sailing

Oct 25, 2026

Plaza Mayor in Madrid, Spain.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

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

Barcelona (Tarragona)

Palma de Mallorca

Aboard

Wind Star

From

Madrid, Spain

1 Sailing

Oct 27, 2026

1 Sailing

Oct 27, 2026

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

Windstar

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

Rome (Civitavecchia)

Aboard

Wind Surf

From

Civitavecchia, Rome, Italy

1 Sailing

Nov 3, 2025

1 Sailing

Nov 3, 2025