Yachtsman’s Mediterranean Rivieras & Madrid Cruise Tour
GO ALL IN
Go All In
Drinks, gratuities, and WiFi included plus up to 40% off selected sailings.

Cruise overview
Experience the world’s most renowned yachting playground on a spectacular journey where you’ll dock alongside other luxury yachts at entrancing ports and secluded harbors, as well as go deep into Spain to explore Madrid. The magnificent ports of the Rivieras each have their own distinctive allure — from the casinos and castles of Monaco to the glitz and glam of Cannes to the stunning vistas and charm of Portofino. What’s special about this journey is that it takes you deeper into Spain. In Madrid, you’ll have two full days and four nights to explore the capital’s key attractions and immerse yourself in its vibrant culture with a 5-star hotel as your home base. Beat the crowds with early entry to the Prado Museum, where you’ll revel in Spanish masterpieces and the largest collection of Italian art outside of Italy. Learn to cook tapas at a boutique cooking school. Enjoy a fiery flamenco show while enjoying a three-course dinner created by a Michelin star chef. You’ll also spend a day in Segovia, a medieval city (also UNESCO World Heritage site) featuring an ancient Roman aqueduct that winds around the edge of town. Get a guided tour through the city’s Gothic-style Cathedral, stopping at the iconic Alcázar castle. Indulge in a wine tasting at the Cavas Cordoniu cellars in the beautiful Penedés wine region of Catalonia, where you’ll learn the art of wine tasting and the secrets of the 450-year history of the winery over a delightful lunch. Your travel between Barcelona and Madrid will be in Comfort Class via high-speed train. To make your trip even more convenient, Windstar picks up your luggage and ensures it will be waiting for you when you arrive at your hotel. It’s the final touch on a once-in-a-lifetime experience.
Itinerary
Rome
Rome, Italy, the Eternal City, is a stunning blend of ancient history and vibrant modern life. Iconic landmarks like the Colosseum, Vatican City, and the Pantheon showcase its glorious past. Cobblestone streets lead to charming piazzas, bustling markets, and world-renowned museums. Rome’s culinary scene delights with traditional Italian cuisine and lively cafes. The city’s rich culture, impressive architecture, and warm, welcoming atmosphere make it an unforgettable destination for travellers.
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Portofino
Monte-Carlo
Sanary-sur-Mer
Palamós
Barcelona
Madrid
Madrid
Madrid
Madrid
Gracious Staterooms
Amenities
- Queen or Twin Configuration
- Lounge Area
- Shower
- Toiletries Provided
- Room Service Available
- Suite Benefits
- TV
- Wi-Fi (Additional Cost)
- Safe
- Hair Dryer
- Desk
- Vanity Area
- Telephone
- Mini Bar (Additional Cost)
Ship features
Wind Surf marries classic sailing romance with modern yacht comforts and upscale amenities.
- Five large sails up to 67.5 m high
- Full-service spa, fitness centre and wellness offerings
- Multiple dining outlets including AmphorA, Stella Bistro and Candles
- Open-bridge policy allowing guest visits
- Watersports platform with snorkeling, paddleboards etc.
- Indoor & outdoor lounges, bars, library, photo gallery
- Pools, two whirlpools and reclining decks
- Boutique shopping and signature shop










