Yachtsman’s Mediterranean Rivieras & Madrid Cruise Tour
 
Barcelona to Rome
Fri Jun 26, 2026 - Tue Jul 7, 2026,
 11 days
 on Wind Surf
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Starting from $7,499 USD
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Barcelona to Rome
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.
voyage map

What's Included?

New Madrid Cruise Tours – 4 night (5 day) pre- or post-cruise tour available on select itineraries starting or ending in Barcelona, Spain. This tour is also available on select 2025 itineraries.
  • 9 Meals included – breakfast (4), lunch (3), dinner (2)
  • 4 Nights at a 5-Star hotel
  • All Entrance fees, including insider tour of the Real Madrid CF Museum and Bernabéu Stadium, and early entrance to the Prado Museum – known for its comprehensive collection of work by Spanish masters from El Greco to Goya.
  • Traditional Cava tasting at the renowned Codorniu wine cellar and an in-depth tour explaining the intricacies of the traditional cava bottling process.
  • Innovative Flamenco show at the world’s most famous Flamenco Tablao, Corral de la Moreria, while enjoying a three-course gourmet meal created by a Michelin Star chef.
  • Tour of the countryside town of Segovia, a UNESCO World Heritage Site and medieval city characterized by its iconic Roman aqueduct and Alcazar de Segovia, the oldest active royal palace in Europe.
  • Experience high speed train travel like the locals, as you opt for this mode of transportation after a full day of touring.
  • All transfers from yacht to hotel, to and from sites and to the airport, so you can relax and enjoy your intentionally planned days without hassle,
  • Yachtsman’s Harbors of the Rivieras Cruise
Popular Highlights
Monte Carlo
Overnight in Monte Carlo, where the Royal Palace and Grand Casino beckon.
 
Penedés Region
In the Penedés Region of Catalonia, Spain you’ll have spectacular views of the Montserrat Mountains as you sip cava sparkling and learn about the traditional bottling process.
Portofino
Sip a cappuccino at the fabled Portofino marina and admire the Italian artistry of the designer shops, terra cotta buildings and cafes.
 
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Fri Jun 26
Arrive in Madrid
Arrive:  
Depart:  
Watersports Platform: 
Sat Jun 27
Madrid: Santiago Bernabéu Stadium & Royal Palace
Arrive:  
Depart:  
Watersports Platform: 
Sun Jun 28
Madrid: Prado Museum & El Retiro Park
Arrive:  
Depart:  
Watersports Platform: 
Mon Jun 29
Segovia, Spain
Arrive:  
Depart:  
Watersports Platform: 
Tue Jun 30
Barcelona
Arrive:  
Depart:  
Watersports Platform: 
Tue Jun 30
Barcelona
Arrive:  
Depart:  5:00 PM
Watersports Platform: 
Wed Jul 1
Palamos
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Thu Jul 2
Sanary-sur-Mer
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Fri Jul 3
Monte Carlo
Arrive:  8:00 AM
Depart:  11:59 PM
Watersports Platform: 
Sat Jul 4
Cannes
Arrive:  7:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sun Jul 5
Portofino
Arrive:  9:00 AM
Depart:  9:00 PM
Watersports Platform: 
Mon Jul 6
Portoferraio
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Jul 7
Rome
Arrive:  7:00 AM
Depart:  
Watersports Platform: 
Accommodations & Pricing
Category B
Category B
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $7,499 per guest
? All-inclusive price from $8,192 per guest
The Windstar Life
The Windstar staff-to-guest ratio is 1:1.5, and it shows.The moment you board you’ll feel it: an ever-attentive crew at your service, providing you with what you want and need, when you want and need it.
Friendly and Relaxed Atmosphere
Signature Onboard Barbecue
Cooking Demonstrations
ALL DATES &
FARES
Pick Your Perk
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited select beer, wine, and cocktails, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sun, Jul 20 - Fri, Aug 1, 2025
WIND SURF
$7,992
$7,299
Fri, Aug 8 - Tue, Aug 19, 2025
WIND SURF
$7,792
$7,099
Mon, Nov 3 - Sat, Nov 15, 2025
WIND SURF
$7,592
$6,899
Wed, Apr 22 - Mon, May 4, 2026
WIND SURF
$8,091
$7,299
Fri, Jun 26 - Tue, Jul 7, 2026
WIND SURF
$8,192
$7,499
THIS
SAILING
Mon, Sep 7 - Sat, Sep 19, 2026
STAR LEGEND
$8,691
$7,899
Sun, Oct 25 - Wed, Nov 4, 2026
WIND SURF
$7,394
$6,899