Winter Riviera & Madrid Cruise Tour

From $7,299 per person

12 days

Ship: Star Legend

Winter Riviera & Madrid Cruise Tour
Windstar Cruises

Luxuriate in the unhurried pace of the Riviera&rsquo;s off-season and immerse yourself in the magic of Madrid.<br />
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Docking in some of world&rsquo;s most iconic coastal cities &ndash; Rome, Nice, Florence, and Barcelona &ndash; you&rsquo;ll have the rare opportunity to explore landmarks such as the Roman Coliseum, the Piazzale Michelangelo and the Sagrada Familia unfettered by crowds, while enjoying quiet moments in intimate cafés, trendy eateries, artisan shops, and galleries tucked away on cobblestone streets.<br />
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Traveling Comfort Class via high-speed train between Barcelona and Madrid, you&rsquo;ll have two full days and four nights to take in the capital&rsquo;s vibrant culture and rich history, with a gorgeous 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 daytrips including a visit to a 450-year-old winery in the beautiful Penedés region complete this unforgettable journey.

Journey Summary

  • Day 1 - Dec. 16, 2025, Tue. - Madrid, Spain
  • Day 2 - Dec. 17, 2025, Wed. - Madrid, Spain
  • Day 3 - Dec. 18, 2025, Thu. - Madrid, Spain
  • Day 4 - Dec. 19, 2025, Fri. - Barcelona
  • Day 5 - Dec. 20, 2025, Sat. - Barcelona
  • Day 6 - Dec. 21, 2025, Sun. - Barcelona
  • Day 7 - Dec. 22, 2025, Mon. - Nice
  • Day 8 - Dec. 23, 2025, Tue. - Nice
  • Day 9 - Dec. 24, 2025, Wed. - Genoa, Italy
  • Day 10 - Dec. 25, 2025, Thu. - Livorno
  • Day 11 - Dec. 26, 2025, Fri. - Livorno
  • Day 12 - Dec. 27, 2025, Sat. - Rome

Itinerary Highlights

Head to Castel Sant&rsquo;Angelo in Rome for an ice-skating adventure.&nbsp; Afterwards, stop by the nearby markets, cozy cafes, and festive lights that line the streets.

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Detailed Itinerary

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

Day 1 - December 16, 2025

Madrid, Spain

Settle into Madrid’s charm the moment you land at the vibrant Madrid-Barajas International Airport. After picking up your reserved car, enjoy a leisurely drive to your luxurious 5-star hotel. Take your time as you check in and make yourself comfortable. Once settled, the rest of the day is yours to unwind and explore. Just steps from your hotel, discover the iconic Gran Via, a bustling strip known as “Spanish Broadway.” Indulge in world-class shopping, treat yourself to fine dining, or simply take in the historic vibe of this vibrant city. Your experience includes seamless transfers from the airport to your hotel and a delightful overnight stay in Madrid.

Day 2 - December 17, 2025

Madrid, Spain

Wake up to a hearty breakfast at your hotel before embarking on a day packed with unforgettable moments in beautiful Madrid. Your first stop is the iconic Santiago Bernabéu Stadium, home to Real Madrid CF since 1947. Enjoy a breathtaking view of the stadium, tour the club’s museum, and relive historic football moments. Wander through displays of legendary trophies and memorabilia that shaped this world-renowned team. Next, savor delicious local flavors at a traditional Spanish restaurant for lunch. Then, journey to the majestic Royal Palace, a masterpiece of architecture and the largest working palace in Europe. Stroll through lavish halls adorned with grand tapestries, exquisite paintings, and stunning sculptures. Don’t miss the chance to marvel at areas like the Grand Staircase and the historic Armoury Square, immersing yourself in centuries of Spain's regal past.As the sun sets, your experience comes alive at Corral de la Morería, rightly called Madrid’s “Cathedral of Flamenco.” Enjoy a dazzling flamenco performance by top artists in an intimate setting while delighting in a sumptuous three-course dinner crafted by a Michelin Star chef. This evening promises to be as fiery and passionate as the art of flamenco itself. Includes meals, entrance to Santiago Bernabéu Stadium and Real Madrid CF Museum, the flamenco show, and a stay at a Madrid hotel.

Day 3 - December 18, 2025

Madrid, Spain

Start your day with a delightful hotel breakfast before skipping the line and stepping into the iconic Prado Museum, renowned for its unmatched collection of masterpieces by Spanish legends like Velázquez, El Greco, Goya, and Bosch. Thanks to exclusive early entrance, you’ll explore the museum’s stunning galleries an hour before the crowds! Beyond Spanish art, admire a grand array of European works and one of the richest collections of Italian art outside of Italy. Next, unwind at El Retiro Park, Madrid’s green heartbeat and a UNESCO World Heritage Site. Wander through lush gardens graced with historic sculptures, discover a nearly 400-year-old Mexican conifer, or relax by the charming lake. You can even rent a rowing boat for a touch of adventure! Don’t miss the elegant Glass Palace, a shimmering example of 19th-century cast-iron architecture.The afternoon is yours to explore the city at your own pace! In the evening, immerse yourself in Spain’s culinary wonders at a boutique cooking school. Learn the art of crafting traditional tapas and then savor a chef-curated 5-course dining experience, complete with delightful pairings of Spanish wines.

Day 4 - December 19, 2025

Barcelona

Begin your morning with a delightful breakfast at your Madrid hotel before heading out on an unforgettable journey to Segovia. Nestled in the Castile and León region, this enchanting medieval city, recognized as a UNESCO World Heritage Site, promises to transport you back in time. Marvel at the Roman aqueduct, a remarkable architectural feat weaving through the city. Stroll through Plaza Mayor, where the Gothic elegance of Segovia Cathedral’s pinnacled apse captures the imagination. A guided tour of the cathedral will unlock its fascinating history and its nickname, "Lady of the Cathedrals." Savor a traditional Segovian feast in a charming local restaurant before venturing to the Alcázar of Segovia, a fairy-tale fortress that has inspired iconic fictional castles. Built in the 12th century, its grand halls and towering spires are steeped in history, having served as the residence of 22 kings. Return to Madrid, where the high-speed train will whisk you comfortably to Barcelona in Comfort Class as your luggage awaits you in your hotel room. Upon arrival, you'll be chauffeured to a luxurious 5-star hotel. End the day with a delicious Catalan dinner, reliving the day’s magical experiences.

Day 5 - December 20, 2025

Barcelona

Start your day with a leisurely breakfast before heading to the enchanting Penedès region of Catalonia. Known for its ideal climate—sunny skies, mild temperatures, and just the right amount of rainfall—this area is a wine lover’s haven. Today’s adventure takes you to the historic Codorníu wine cellars, where cava has been made for over 450 years. Walk through the ancient cellars, learn about the art of crafting cava, and soak in the rich history while sampling a flight of their finest sparkling wines. Afterward, savor a delicious three-course lunch, a perfect complement to your vineyard visit. The day continues with a scenic journey to Barcelona, where a guided panoramic tour awaits before you board your ship, ready for the next chapter of your journey.

Day 6 - December 21, 2025

Barcelona

In Barcelona, old-world charm gracefully intertwines with modern vibrancy. Stroll through narrow lanes steeped in history or wander boulevards bustling with energy. Savory aromas from quaint tapas bars meet the avant-garde creations of trendy chefs, while warm greetings from the city's stylish locals create a welcoming atmosphere. Explore UNESCO wonders like Antoni Gaudí’s surreal architecture, or gaze up at the breathtaking La Sagrada Familia—with intricate spires that seem to touch the heavens.

Day 7 - December 22, 2025

Nice

Discover the captivating charm of Nice, a city that perfectly showcases the Riviera's allure. Wander through its streets adorned with vibrant flowers. Explore bustling markets and world-renowned museums like the Musée Chagall and Musée Matisse, each offering a glimpse into the region's rich history and art. Stroll along the iconic Promenade des Anglais, where the sun sparkles on the water. Whether you're enjoying a relaxing moment in a chaise bleu or savoring a flavorful bowl of bouillabaisse at a cozy local restaurant, Nice invites you to embrace its unique blend of beauty and sophistication.

Day 8 - December 23, 2025

Nice

Nice welcomes you with its colorful streets filled with flowers, lively markets, and fascinating museums like the Musée Chagall and Musée Matisse. Feel the true spirit of the Riviera as you relax on the famous Promenade des Anglais. Sink into a comfy blue chair and let the gentle Mediterranean breeze sweep over you while watching the world pass by. When hunger beckons, savor a bowl of freshly made bouillabaisse, one of the region's tastiest delights, in a welcoming local spot.

Day 9 - December 24, 2025

Genoa, Italy

Explore the timeless allure of Genoa, a gem on Italy’s northwest coast. Steeped in maritime legacy, this lively destination captivates with its historic old town and stunning architecture, blending medieval, Renaissance, Baroque, and Gothic styles. Discover a city where luxury and tradition meet, as you stroll past grand palaces or dive into its modern art scene. Don’t miss its bustling food markets, brimming with flavor and flair, as you taste your way through the birthplace of pesto. Genoa promises a perfect mix of elegance, culture, and irresistible charm.

Day 10 - December 25, 2025

Livorno

Discover Livorno—a hidden gem offering more than just a gateway to Florence and Pisa. With its vibrant harbor, Renaissance charm, and access to Tuscany's rolling wine country, this seaside town invites exploration at every turn. Meander along the tranquil waterside promenade or hop aboard a canal ride through the enchanting Venezia Nuova quarter. Seafood connoisseurs and wine enthusiasts alike will delight in Livorno’s culinary treasures.

Day 11 - December 26, 2025

Livorno

Nestled along the dazzling Tuscan coastline, Livorno is a hidden gem with something for everyone. Imagine strolling along a breezy promenade that hugs the sea or gliding through serene canals in the charming Venezia Nuova district. Renowned for its fresh, flavorful seafood and Renaissance architecture, this port city also opens the door to iconic destinations like Florence and Pisa. Venture a bit further, and you'll encounter enchanting wineries where you can sip world-class wines amid rolling green vineyards. Livorno isn’t just a gateway; it’s a destination filled with warm, unforgettable moments.

Day 12 - December 27, 2025

Rome

Step into the charm of Rome, where history and modern life harmoniously blend together. Towering skyscrapers share city blocks with ancient ruins and grand cathedrals, creating a rich tapestry of old and new. Wander through stylish boutiques, enjoy a cup of coffee at a bustling café, and soak in the vibrant atmosphere. Then, immerse yourself in the city's timeless stories. Begin at the Vatican—marvel at Michelangelo’s Sistine Chapel and the majestic St. Peter’s Basilica. Discover masterpieces by Raphael and Bernini, each worthy of your admiration. Nearby, the Colosseum and Roman Forum whisper tales of ancient glory, while the Trevi Fountain invites you to toss a coin, ensuring a return to this unforgettable city. Rome’s beauty feels like a gift you’ll always carry with you.

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Dec 16, 2025

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