Madrid & Southern Spain Winter Escapes Cruise Tour

From $6,899 per person

12 days

Ship: Star Legend

Madrid & Southern Spain Winter Escapes Cruise Tour
Windstar Cruises

Embrace the essence of Spain on a voyage along its splendid coasts in off-peak season combined with a special journey on land to explore Madrid.<br />
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Cornering the southern tip of Iberia, you&rsquo;ll be captivated by the imposing heights and legend of Gibraltar. In Costa del Sol&rsquo;s temperate Málaga, you may find yourself sampling local delicacies seated comfortably at outdoor cafés. From uncrowded galleries adorned with Picasso&rsquo;s work, to the architectural wonders of Gaudi in Barcelona, you&rsquo;ll gaze in delight at every turn.<br />
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Traveling via high-speed train between Barcelona and Madrid, you&rsquo;ll have four nights to take in the capital&rsquo;s vibrant culture and rich history, with a 5-star hotel as your home base.<br />
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Exclusive experiences such as early entry to the renowned Prado Museum, a flamenco dinner show at Spain&rsquo;s only Michelin-starred tablao restaurant, and a daytrip to a 450-year-old winery in the beautiful Penedés region complete this unforgettable journey.

Journey Summary

  • Day 1 - Dec. 13, 2025, Sat. - Málaga
  • Day 2 - Dec. 14, 2025, Sun. - Málaga
  • Day 3 - Dec. 15, 2025, Mon. - Gibraltar
  • Day 4 - Dec. 16, 2025, Tue. - Cartagena
  • Day 5 - Dec. 17, 2025, Wed. - Valencia
  • Day 6 - Dec. 18, 2025, Thu. - Palma de Mallorca
  • Day 7 - Dec. 19, 2025, Fri. - Barcelona
  • Day 8 - Dec. 20, 2025, Sat. - Barcelona
  • Day 9 - Dec. 21, 2025, Sun. - Madrid, Spain
  • Day 10 - Dec. 22, 2025, Mon. - Madrid, Spain
  • Day 11 - Dec. 23, 2025, Tue. - Madrid, Spain
  • Day 12 - Dec. 24, 2025, Wed. - Madrid, Spain

Itinerary Highlights

In Palma de Mallorca explore the city&rsquo;s well-known Moorish architecture.<br />
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Detailed Itinerary

Day-by-day description of your cruise and cruise activities.

Day 1 - December 13, 2025

Málaga

Here, on the shores of Costa del Sol, the Andalusian spirit thrives. Be sure to include an optional visit to see the brilliant and comprehensive collection of Picasso&rsquo;s work at Museo Picasso Málaga, a tribute to this artistic genius in the city of his birth. Or you may choose to opt for a visit to the beautiful village of Mijas, where picturesque Andalusian country life creates some of the world&rsquo;s best wines.&nbsp;

Day 2 - December 14, 2025

Málaga

Here, on the shores of Costa del Sol, the Andalusian spirit thrives. Be sure to include an optional visit to see the brilliant and comprehensive collection of Picasso&rsquo;s work at Museo Picasso Málaga, a tribute to this artistic genius in the city of his birth. Or you may choose to opt for a visit to the beautiful village of Mijas, where picturesque Andalusian country life creates some of the world&rsquo;s best wines.&nbsp;

Day 3 - December 15, 2025

Gibraltar

It&rsquo;s an odd bit of Britain here at the toe of Spain, with Barbary apes and miles of tunnels as well as traditional red phone boxes. Legend says Gibraltar was one of the two pillars erected by Hercules to mark the edge of the world. Take the cable car to the top to see if you can see it from here. No, that&rsquo;s not it. That&rsquo;s just Africa. What a view.<br />

Day 4 - December 16, 2025

Cartagena

The walled town of Cartagena is a popular seaport with a large naval shipyard. The seashore offers a wide range of activities from windsurfing to good snorkeling to sailing. From Cartagena you can easily explore the ancient city of Murcia, the coastal resorts of Mazarrón, Cala Cortina, and Cabo de Palos or a little further north, the world famous resort of Mar Menor.

Day 5 - December 17, 2025

Valencia

This captivating city is best when savored slowly. Although Valencia&rsquo;s religious architecture is remarkable, and the Lonja, one of Europe&rsquo;s most elegant buildings is a UNESCO World Heritage Site, take time for an optional experience &mdash; <em>paella</em>. You&rsquo;ll learn the local secrets of this gastronomic masterpiece as you cook it, eat it, and toast it with the region&rsquo;s perfectly matched local wines.
Want insider advice on where to find the tastiest restaurants, most unique local markets, authentic culinary shops, and hidden watering holes? <a href="http://blog.windstarcruises.com/2001/01/local-dining-tips-valencia-cultural-wonder/" target="_blank">Check out Valencia&rsquo;s <strong>Local Dining Tip Curated by Saveur</strong> on our blog</a>.

Day 6 - December 18, 2025

Palma de Mallorca

Mallorca is steep, green, and fringed with enticing coves and more than 200 lush beaches. But all that natural beauty is just the beginning. Stroll along the tree-shaded Paseo de Born in search of tapas. Shop for a Siurell; a traditional red, green, and white clay whistle dating back to the time of the Moors. Watch the street performers on the piazza around the church, or cross the island to beautiful Sóller. Not to be missed is the cultural landscape of the Serra de Tramuntana, a UNESCO World Heritage Site.

Day 7 - December 19, 2025

Barcelona

The old meets the new in this sunny Catalan metropolis, where narrow alleyways contrast with grand boulevards, trendy cuisine meets homemade tapas, and everywhere you&rsquo;re greeted by the warm, welcoming smiles of the fashionable locals. Don&rsquo;t miss UNESCO sites like the mind-boggling architecture of Antoni Gaudí or La Sagrada Familia Cathedral, with its eight decorative spires soaring hundreds of feet into the sky.

Day 8 - December 20, 2025

Barcelona

The old meets the new in this sunny Catalan metropolis, where narrow alleyways contrast with grand boulevards, trendy cuisine meets homemade tapas, and everywhere you&rsquo;re greeted by the warm, welcoming smiles of the fashionable locals. Don&rsquo;t miss UNESCO sites like the mind-boggling architecture of Antoni Gaudí or La Sagrada Familia Cathedral, with its eight decorative spires soaring hundreds of feet into the sky.

Day 9 - December 21, 2025

Madrid, Spain

After breakfast at the hotel, you&rsquo;ll kick off your day with a visit to the world-famous Santiago Bernabéu stadium&mdash;host to Real Madrid CF since 1947. Fans of the football (aka American soccer) will go wild over the panoramic view of the inside of the renovated stadium, with admission to the Real Madrid CF Museum, where you&rsquo;ll learn about the history of the club and its members, take pictures next to famous trophies and watch the club&rsquo;s most iconic moments. Next, you&rsquo;ll enjoy lunch at a local restaurant. The tour continues to the Royal Palace, an awe-inspiring architectural wonder and the largest functioning palace in Europe. You&rsquo;ll learn about the site&rsquo;s rich history, capture pictures at Armoury Square, get a chance to walk the iconic marble Grand Staircase, and explore majestic rooms and spaces displaying sculptures, paintings, tapestries and jewels offering insight into the 18-century Spanish Monarchy. In the evening, you&rsquo;ll head to renowned tablao Corral de la Morería (Madrid&rsquo;s &ldquo;Cathedral of Flamenco) to see a fiery flamenco show performed by some of Spain&rsquo;s top dancers and musicians, while enjoying a three-course gourmet meal created by a Michelin Star chef.<br />
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(Includes breakfast, lunch, dinner and flamenco show, entrance to Bernabéu Stadium and Real Madrid CF Museum, overnight in Madrid hotel)

Day 10 - December 22, 2025

Madrid, Spain

After breakfast at the hotel, you&rsquo;ll head right to the Prado Museum to take in the world&rsquo;s richest and most comprehensive collection of Spanish works from Spanish masters Valázquez, El Greco, Goya and El Bosco. Your early access allows you to skip the line and enter the museum one hour before they open. The museum also houses a vast collection of classical European paintings and sculptures, including the largest collections of Italian art outside of Italy. Next, you&rsquo;ll head to the famous &ldquo;El Retiro Park,&rdquo; a UNESCO World Heritage Site offering a vast green oasis in the heart of the city. Stroll through a variety of gardens with interesting monuments, view a nearly 400-year-old Mexican conifer, sit by the lake or rent a rowing boat, and explore the exhibitions halls, including the Glass Palace, a glass pavilion built in 1887, regarded as one of Spain&rsquo;s finest examples of cast-iron architecture. After enjoying the park, you&rsquo;ll have free time to explore and find lunch on your own. In the evening, you&rsquo;ll be immersed in a unique culinary experience at a boutique cooking school. You&rsquo;ll learn the art of preparing tapas, then enjoy them along with a chef-prepared entree and two desserts for a 5-course tasting menu served with a bottomless wine pairing of five different Spanish wines.<br />
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(Includes breakfast, dinner, early entrance to Prado Museum, cooking class, overnight in Madrid hotel)

Day 11 - December 23, 2025

Madrid, Spain

You&rsquo;ll have breakfast at your hotel in Madrid before taking off for an incredible day in Segovia, a medieval city located in Castile and Leó, designated a UNESCO World Heritage Site. You&rsquo;ll look back in time as you admire the incredible Roman Aqueduct winding its way around the edge of town. You&rsquo;ll visit Plaza Mayor, a town square framed by the beautiful pinnacles of the apse of the Cathedral, built in Castilian Late Gothic style, then head inside to meet your guide and tour the Cathedral, learning about its historical significance and architectural highlights that have earned it the name Lady of the Cathedrals. Next, you&rsquo;ll enjoy a classic Segovian lunch at a delightful restaurant, followed by a stop at the renowned Alcázar of Segovia, a medieval castle built in the 12<sup>th</sup> century that has served as home for 22 kings and inspired the design of castles in shows and movies, including Cinderella&rsquo;s castle. Afterwards, you&rsquo;ll travel back to your hotel in Madrid and enjoy the evening at your leisure.

Day 12 - December 24, 2025

Madrid, Spain

After breakfast at your hotel, you&rsquo;ll be driven to the Madrid-Barajas International Airport for your flight home.<br />
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(Includes breakfast and transfers to the airport)

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Dec 13, 2025

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