Yachtsman’s Mediterranean Rivieras & Madrid Cruise Tour

Detailed Itinerary

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

Day 1

Madrid, Spain

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)

Day 2

Madrid, Spain

After breakfast at the hotel, you’ll kick off your day with a visit to 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. Next, you’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’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. 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.

(Includes breakfast, lunch, dinner and flamenco show, entrance to Bernabéu Stadium and Real Madrid CF Museum, overnight in Madrid hotel)

Day 3

Madrid, Spain

After breakfast at the hotel, you’ll head right to the Prado Museum to take in the world’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’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. After enjoying the park, you’ll have free time to explore and find lunch on your own. In the evening, you’ll be immersed 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, dinner, early entrance to Prado Museum, cooking class, overnight in Madrid hotel)

Day 4

Barcelona

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 12^th 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.

Day 5

Barcelona

After breakfast at your hotel, you’ll be driven towards 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, where you will enjoy your tasting flight. By the time you head to a delicious three-course lunch, you’ll have 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, travel to Barcelona)

Day 6

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.

Day 7

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.

Day 8

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.

Day 9

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.

Day 10

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.

Day 11

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.

Day 12

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.

Day 13

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.

Ship

Your cruise ship

About this ship

Star Legend

Star Legend is a boutique, all-suite yacht that exemplifies Windstar Cruises’ signature style of immersive, small-ship luxury. Carrying just 312 guests, the vessel offers a relaxed yet sophisticated atmosphere, designed for discerning travelers who seek personal space, attentive service, and the ability to reach off-the-beaten-path destinations in comfort and style.

Originally launched in 1992 and transformed in 2021 as part of Windstar’s ambitious $250 million Star Plus Initiative, Star Legend emerged from its renovation with a new vitality. The ship was lengthened by 84 feet, allowing for expanded public areas, new dining concepts, and additional all-suite accommodations—all while preserving the sense of intimacy that defines the Windstar experience.

The 156 suites onboard range from 277 to 820 square feet, all offering sweeping ocean views. Interiors are designed with a contemporary, understated elegance, featuring warm wood tones, plush furnishings, and a palette drawn from the sea and sky. Many suites include private verandas or French balconies, while all offer walk-in closets, marble bathrooms with dual vanities, and fine details such as L’Occitane bath amenities, high-thread-count linens, and Illy espresso machines.

Dining on Star Legend is a true highlight. Guests enjoy a variety of culinary venues, all included in the fare and all rooted in Windstar’s commitment to quality and creativity. Amphora, the main dining room, serves globally inspired dishes in an open-seating setting. Candles, the ship’s romantic outdoor venue, offers expertly prepared steaks under the stars. Cuadro 44 by James Beard Award–nominated chef Anthony Sasso presents modern Spanish cuisine in a cozy, wine-bar-style space, while the Star Grill by Steven Raichlen delivers global barbecue flavors in an al fresco setting. The Yacht Club Café provides a more casual option for coffee, pastries, and light bites throughout the day.

Life onboard is designed for both enrichment and relaxation. The World Spa by Windstar offers a full menu of treatments, a thermal suite, and a serene atmosphere, while the fitness center features modern equipment and instructor-led wellness classes. The open decks include an infinity-style pool and whirlpools with panoramic views, while the ship’s watersports platform at the stern offers complimentary access to kayaks, paddle boards, snorkeling gear, and more—available when anchored in select destinations.

Because of its size and advanced maneuverability, Star Legend is uniquely equipped to access smaller ports and remote harbors. Whether exploring the storied coastlines of the Mediterranean, the rugged beauty of Northern Europe, or the exotic islands of Southeast Asia, the ship brings guests closer to the cultures and landscapes they’ve come to discover.

Blending elegance, intimacy, and destination-driven itineraries, Star Legend offers a yachting experience that is as enriching as it is indulgent—perfect for travelers who seek the freedom of the open sea without sacrificing the comforts of modern luxury.

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Yachtsman’s Mediterranean Rivieras & Madrid Cruise Tour

Journey Summary

Detailed Itinerary

Day 1

Day 2

Day 3

Day 4

Day 5

Day 6

Day 7

Day 8

Day 9

Day 10

Day 11

Day 12

Day 13

Dates and Prices

(per person*)

Ship

Your cruise ship

About this ship

Star Legend

Deckplans

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