Embark on a luxurious journey through Tuscany’s rolling vineyards, medieval hilltop towns, and exquisite cuisine. From Florence to the Val d’Orcia, this bespoke road trip is designed for those seeking elegance, indulgence, and authentic Italian charm.
Tuscany is a region of postcard-perfect landscapes, timeless art, and culinary brilliance. A luxury road trip through this iconic destination invites you to explore its vineyards, medieval villages, and historic cities, all while indulging in unparalleled comfort and sophistication.
Picture yourself savoring world-class wine in a centuries-old cellar, dining under the stars in a private villa, or wandering through cobblestoned streets that seem frozen in time.
Tuscany is not just a destination—it’s an experience of la dolce vita at its finest.
Begin your journey in Florence, a city synonymous with art, history, and style. Check into the lavish Hotel Savoy, located steps from the Duomo, where contemporary luxury meets Florentine charm.
Start your day with a private guided tour of the Uffizi Gallery, home to masterpieces by Botticelli and Michelangelo. Afterward, enjoy a curated shopping experience at the Ponte Vecchio, known for its exquisite jewelry.
In the evening, indulge in a Michelin-starred dinner at Enoteca Pinchiorri, pairing inventive cuisine with Tuscany’s finest wines. Conclude your Florence stay with a rooftop cocktail overlooking the city’s skyline.
Drive into the Chianti region, where rolling hills are adorned with vineyards and olive groves. Stay at the exclusive Castello di Casole, a restored 10th-century castle offering panoramic views and exceptional service.
Embark on a private wine-tasting tour, visiting renowned estates like Antinori nel Chianti Classico. Learn the art of winemaking while sampling Super Tuscans paired with local cheeses and cured meats.
Enhance your experience with a hot air balloon ride over the vineyards at sunrise, followed by a gourmet picnic breakfast amid the vines. In the evening, savor authentic Tuscan dishes at Ristorante Badia a Coltibuono, a historic abbey-turned-restaurant.
Continue to Siena, a city renowned for its Gothic architecture and vibrant culture. Check into the charming Grand Hotel Continental, housed in a 17th-century palace.
Explore the Piazza del Campo, one of Europe’s most beautiful squares, and climb the Torre del Mangia for sweeping views of the city and countryside. Enjoy a private tour of Siena Cathedral, known for its intricate marble floors and exquisite artwork.
For dinner, experience La Taverna di San Giuseppe, a cozy, Michelin-recommended spot featuring traditional Tuscan fare and an impressive wine cellar.
Your journey continues to the Val d’Orcia, a UNESCO World Heritage site known for its ethereal beauty. Stay at the ultra-luxurious Rosewood Castiglion del Bosco, an exclusive estate offering private villas and a world-class spa.
Spend your days exploring the picturesque towns of Pienza, famous for its pecorino cheese, and Montepulciano, renowned for its Vino Nobile. Enjoy a private truffle-hunting experience in the countryside, followed by a gourmet lunch featuring your finds.
Relax with a sunset aperitivo at your villa, overlooking the golden fields, and indulge in a farm-to-table dinner prepared by a private chef.
Day 1: Arrival in Florence
Day 2: Explore Florence’s Elegance
Day 3: Journey to Chianti
Day 4: Medieval Siena
Day 5: Val d’Orcia Escape
Tuscany offers an unparalleled blend of natural beauty, cultural richness, and refined luxury. Whether you're savoring the region’s world-renowned wines, exploring its medieval treasures, or simply relaxing in a private villa, every moment is designed to inspire and indulge.
Contact your personal travel designer today to craft your bespoke Tuscan escape.
