Yachtsman’s Mediterranean Rivieras & Madrid Cruise Tour
 
Barcelona to Rome
Mon Sep 7, 2026 - Sat Sep 19, 2026,
 12 days
 on Star Legend
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Starting from $7,899 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
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Day 1: Arrive in Madrid
Upon your arrival at Madrid-Barajas International Airport, you’ll pick up your reserved car and drive to your 5-star hotel. Check in and you’ll have the entire afternoon and evening to spend at your leisure with world-class shopping and dining just steps away on the iconic Gran Via (the “Spanish Broadway”).
 
(includes transfers from the airport to your hotel and overnight in Madrid hotel)
 
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Day 2: Madrid: Royal Palace and Santiago Bernabéu Stadium
After breakfast at the hotel, you’ll kick off your day with a visit to the Royal Palace, an awe-inspiring architectural wonder and the largest functioning palace in Europe. You’ll learn about the site’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. Next, you’re free to enjoy lunch on your own at any of Madrid’s restaurants. The tour continues at the world-famous Santiago Bernabéu stadium—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’ll learn about the history of the club and its members, take pictures next to famous trophies and watch the club’s most iconic moments. In the evening, you’ll head to renowned tablao Corral de la Morería (Madrid’s “Cathedral of Flamenco) to see a fiery flamenco show performed by some of Spain’s top dancers and musicians, while enjoying a three-course gourmet meal created by a Michelin Star chef.
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Day 3: Madrid: Prado Museum and El Retiro Park
After breakfast at the hotel, you’ll head right to the Prado Museum. Your exclusive early access gives you the ability to explore some the world’s richest and most comprehensive collection of Spanish works at your own pace without the crowds. Take your time admiring works from Spanish masters, like Valázquez, El Greco, Goya and El Bosco as you have the museum to yourself for the first hour. 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’ll head to the famous “El Retiro Park,” 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’s finest examples of cast-iron architecture. Afterwards, you will have free time for lunch on your own. Dinner tonight will be an immersive experience, as you participate in a unique culinary experience at a boutique cooking school. You’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.

(Includes breakfast, entrance to Prado Museum, cooking class and dinner, overnight in Madrid hotel)
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Day 4: Segovia, Spain
You’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’ll look back in time as you admire the incredible Roman Aqueduct winding its way around the edge of town. You’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’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 12th century that has served as home for 22 kings and inspired the design of castles in shows and movies, including Cinderella’s castle. You’ll travel back to Madrid, where you’ll catch the high-speed train to Barcelona, traveling in Comfort Class, with your luggage waiting for you at your hotel Barcelona hotel. Upon arrival, you’ll be driven to your 5-star hotel, where you’ll enjoy a Catalan dinner and can share stories about the day.
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Day 5: Barcelona to Ship
After breakfast at your hotel, you’ll be driven to the Penedés Region in Catalonia, where almost all cava and wine is produced due to the region’s favorable climate for growing grapes—mild temperatures, intense sunshine and moderate rainfall. This also makes it great region to visit. This tour will bring you to one of the most renowned Spanish wine cellars: Codorniu. You’ll learn the traditional process of how a bottle of cava is created and the history of the cellars dating back 450 years. Surrounded by the winery’s beautiful architectural complex and gardens, you’ll take an intensive wine tasting course. By the time you head to a delicious three-course lunch, you’ll have learned the art of wine tasting and discovered the secrets of Cavas Codorniu. Later, you’ll travel to Barcelona and take a panoramic tour of the city before embarking on the ship.
(Includes breakfast, lunch, wine tasting, transfer to the ship)
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Day 5: 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’re greeted by the warm, welcoming smiles of the fashionable locals. Don’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.
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Day 6: Palamos
Palamos is famous for the locally caught prawns found in the beautiful bay it sits beside, also known for the excellent swimming, surfing, snorkeling and windsurfing there. Here is the place to try fresh local Catalan cuisine. Two great highlights near Palamos are the Dali Museum, located in his home town of Figueres, and the UNESCO city of Girona, with its medieval architecture, walled Old Quarter and the Roman remains of Forca Vella Fortress.
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Day 7: Sanary-sur-Mer
France’s sunniest city, located on the French Riviera, was originally a small fishing village and still is adorned by a large collection of traditional wooden fishing boats. This is the home of a group of local artisan fisherman who sell their catch daily on the pier and where Jacques Cousteau had a residence, the Villa Baobab.
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Day 8: Monte Carlo
Glide into port in one of Europe’s most exclusive harbors. Mingle with other privileged yachtsmen or step ashore and start walking. The glittering Grand Casino, legendary for its exotic setting on screen and off, is a must see, as is the royal family’s palace and the tomb of Philadelphia-born Princess Grace in the Cathedral.
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Day 9: Cannes
Spend a day wandering among the rich and famous in the chic epicenter of the French Riviera — a world of exclusive boutiques, palm-fringed boulevards, sun-drenched beaches, and elegant sidewalk cafés. Be sure to visit the Avenue of the Stars, where you can place your hands in the prints of international celebrities. An optional escorted walking tour guides you through the best of this extraordinary and stylish city. 
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Day 10: Portofino
With its golden ochre and terracotta buildings, designer shops, and chic cafés, Portofino represents the height of Italian artistry and sophistication. Sip a cappuccino along the fabled marina or enjoy a day of shopping in one of the town’s tempting little boutiques. As you look out over the harbor from the famous Hotel Splendido, it’s hard not to admire the sleek, streamlined beauty of your Windstar ship.
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Day 11: Portoferraio
Pine-scented forests and miles of sandy beach await your arrival on the tranquil island of Elba. Enjoy a glass of local Moscato with the fresh catch of the day before pondering your next move. Perhaps you’ll visit the nearby countryside with its small fishing villages and dramatic mountain passes. Or see the calming beauty of Tuscan Archipelago National Park, a UNESCO Biosphere Reserve.  Or maybe you’ll decide to walk to the nearest beach and dip your toes into the warm Mediterranean.
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Day 12: Porto Ercole
One of Italy’s best secrets and the gateway to Tuscany is charming Porto Ercole with its spectacular sunsets and lovely beaches with amazing snorkeling and diving spots. It is highly encouraged that you find Pizza Grano for an unforgettable slice of pizza and take a stroll on the seaside promenade full of restaurants, artisan shops and fresh seafood.
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Day 13: Rome
In this enchanting city the past and present intersect in perfect harmony. Casually intermingled among ancient ruins and majestic cathedrals are the trappings of a modern metropolis: Skyscrapers,cafes, boutiques selling designer footwear. But of course what you seek first in the heart of Rome is its breathtaking history.  A good place to begin is the Vatican, with its Sistine Chapel and St. Peter’s Basilica. Works by Bernini, Michelangelo, Caravaggio, and Raphael are just a few of those on display, any one of which is worth hours of contemplation. Then the ancient ruins—Colosseum, Forum, Circus Maximus. And of course the Trevi Fountain for the obligatory coins promising your return to the Eternal City.

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 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.
 
Prado Museum
An early admission to Prado Museum allows you to take in the world’s richest and most comprehensive collection of art from Spanish artists at your own pace.
 
Sanary-sur-Mer, France
Wander through the charming old port of Sanary-sur-Mer, France, lined with colorful fishing boats and waterfront cafes.
Santiago Bernabéu stadium
Visit the world-famous Santiago Bernabéu stadium—host to Real Madrid CF. Here, you’ll visit the Real Madrid CF Museum, where you’ll learn about the history of the club, its famous members, and see the club’s trophies up close.
 
Segovia, Spain
In Segovia, Spain, walk the incredible Roman aqueduct winding its way around the city.  This aqueduct is thought to have been built around the first century AD and was a civil engineering feat ahead of its time.
 
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports Platform: 
Mon Sep 7
Arrive in Madrid
Arrive:  
Depart:  
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Tue Sep 8
Madrid: Royal Palace and Santiago Bernabéu Stadium
Arrive:  
Depart:  
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Wed Sep 9
Madrid: Prado Museum and El Retiro Park
Arrive:  
Depart:  
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Thu Sep 10
Segovia, Spain
Arrive:  
Depart:  
Watersports Platform: 
Fri Sep 11
Barcelona to Ship
Arrive:  
Depart:  
Watersports Platform: 
Fri Sep 11
Barcelona
Arrive:  
Depart:  5:00 PM
Watersports Platform: 
Sat Sep 12
Palamos
Arrive:  7:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sun Sep 13
Sanary-sur-Mer
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Sep 14
Monte Carlo
Arrive:  8:00 AM
Depart:  11:59 PM
Watersports Platform: 
Tue Sep 15
Cannes
Arrive:  7:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Sep 16
Portofino
Arrive:  9:00 AM
Depart:  9:00 PM
Watersports Platform: 
Thu Sep 17
Portoferraio
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Fri Sep 18
Porto Ercole
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sat Sep 19
Rome
Arrive:  7:00 AM
Depart:  
Watersports Platform: 
Accommodations & Pricing
Star Porthole Suite
Star Porthole Suite
These rooms represent a nod to the sailing tradition of porthole windows. And while sailors might have had cramped quarters, your 277 square foot stateroom is wonderfully spacious and furnished with all the modern amenities and comforts of home.
? Cruise only from $7,899 per guest
? All-inclusive price from $8,691 per guest
Ocean View Suite
Ocean View Suite
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, and savor a treat from the fresh fruit bowl.
? Cruise only from $8,099 per guest
? All-inclusive price from $8,891 per guest
Ocean View Suite 1
Ocean View Suite 1
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $8,249 per guest
? All-inclusive price from $9,041 per guest
Star Ocean View Suite 1
Star Ocean View Suite 1
As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.
? Cruise only from $8,399 per guest
? All-inclusive price from $9,191 per guest
Ocean View Suite 2
Ocean View Suite 2
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $8,449 per guest
? All-inclusive price from $9,241 per guest
Ocean View Suite 3
Ocean View Suite 3
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $8,599 per guest
? All-inclusive price from $9,391 per guest
Balcony Suite
Balcony Suite
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $9,339 per guest
? All-inclusive price from $10,131 per guest
Star Balcony Suite
Star Balcony Suite
As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.
? Cruise only from $9,499 per guest
? All-inclusive price from $10,291 per guest
Balcony Suite 1
Balcony Suite 1
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $9,599 per guest
? All-inclusive price from $10,391 per guest
Star Balcony Suite 1
Star Balcony Suite 1
As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.
? Cruise only from $9,699 per guest
? All-inclusive price from $10,491 per guest
Deluxe Suite
Deluxe Suite
Brand new Deluxe Suites welcome you with 468 square feet of casually elegant living space and an ocean viewing French balcony. All these suites feature 3rd berths, and a sleep-inducing queen bed easily converted to twins.
? Cruise only from $10,519 per guest
? All-inclusive price from $11,311 per guest
Classic Suite
Classic Suite
Relax in 400 to 530 spacious square feet. Your living area offers beautiful views from the forward-facing window and French doors onto your private veranda. Two spacious closets give you plenty of room to unpack.
? Cruise only from $11,319 per guest
? All-inclusive price from $12,111 per guest
Owner's Suite
Owner's Suite
With 575 square feet, your Owner’s Suite offers separate living room and dining areas. A veranda, Interactive TVs, and a full master bath and separate powder room indulge you in spacious comfort. 
? Cruise only from $12,479 per guest
? All-inclusive price from $13,271 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
Genuine and Thoughtful Crew
Crew Talent Show
Open Bridge
Local and Live Performances
Relax at the Pool or Hot Tub
Complimentary 24 Hour Room Service
Signature Sail Away
Shopping With The Chef
Take In The Sun
Watersports Platform
Enjoy regionally inspired treatments at World Spa by Windstar
Relax With A Morning Yoga Session
ALL DATES &
FARES
Pick Your Perk
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited beer, wine, and cocktails, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Wed, Apr 16 - Sun, Apr 27, 2025
WIND SURF
$8,292
$7,599
Tue, May 13 - Sun, May 25, 2025
WIND SURF
$8,792
$8,099
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
Mon, Sep 7 - Sat, Sep 19, 2026
STAR LEGEND
$8,691
$7,899
THIS
SAILING
Sun, Oct 25 - Wed, Nov 4, 2026
WIND SURF
$7,394
$6,899