Discover safe, luxurious vacations with Inspirato. Create your free account to learn why now, more than ever, Inspirato is the best way to travel.
Tuscany offers the most Inspirato accommodations of any European destination, with eight standalone villas and four hotels. Stay in a restored farmhouse surrounded by olive groves and vineyards at Villa Dante or Villa Azzurri, just outside Florence.
Or, choose from a trio of 11th-century luxury estates—Villa Collina, Villa Bellezza, and La Villetta—near Siena. The historic estates in Val d’Orcia offer the most scenic views; Villa San Bartolomeo and Podere Panico are both standouts, each with a private pool overlooking the rolling Tuscan countryside.
Widely renowned for its rich Brunello wine, the Val d'Orcia region of Tuscany was designed in Renaissance times to be one of the world's most aesthetically pleasing and untouched landscapes. Added to the UNESCO list of World Heritage Sites in 2004, the countryside is depicted by many famous painters and is featured in movies such as The English Patient and Under the Tuscan Sun. Our residences, just south of Siena, are surrounded by world-renowned vineyards and picturesque towns such as Montepulciano and Montalcino.
The Chianti region of Tuscany is famous for its ancient villages, mountainous terrain, and of course, Chianti Classico wine. Take some time to explore the local towns of Greve in Chianti, Siena, and Florence and revel in the classic Tuscan design and charm. A day trip is a must to the towns of Lucca, Pisa, and Cinque Terre.
Our native Destination Concierges can direct you to wineries, authentic trattoria, and ristorantes. Whether you want a private chef for true Tuscan cuisine, a guide to help you hunt for truffles, or a day learning about and driving Ferraris, our on-site staff has relationships with the experts.
From September through December, you can "hunt" one of the world's gourmet delicacies: the elusive truffle. Try hunting In San Giovanni d'Asso, a small village dominated by a castle that is now a truffle museum.
Take off in a hot air balloon and see the Tuscan countryside as few do, including a pass over Siena and Chianti. When you land, you'll be treated to a breakfast that includes local drinks, cheeses, and bread with olive oil.
Dating back to the 14th century, the 13 remaining towers of San Gimignano create a stone skyline rising from the walled city. Stroll through the piazzas and streets and you'll see why the town is known as the Medieval Manhattan.
Harmoniously blending historic grounds with contemporary viticultural techniques, Colle Bereto Winery is a standout. The sprawling estate produces some of the Chianti area's best sangiovese, pinot noir and merlot.
Cugusi is a cheese maker just outside of Montepulciano's city center. At the factory, you can taste and even learn how to make the cheese. Fill a basket with various cheeses, wines and other products of your choosing and have a picnic.
The Castello di Verrazzano is a Chianti winery with vineyards dating to the 12th century; the castle is from the 18th century. Choose between a simple visit, or a "Wine & Food Experience" that leaves both foodies and oenophiles begging for mercy.
At Fattoria Resta, take in history as well as sangiovese. The winery's prized product is named after Martin del Nero, who carved his name into the stone he used to build the 16th century monastery Fattoria Resta now calls home.
Michelin-starred Chef Matia is a maestro of authentic Italian cuisine. Head to the postcard-perfect Antinori estate for a cooking class, where you'll pick up the chef's methods for crafting ravioli and other regional specialties.
Ask your Destination Concierge to book a photo session with the talented people at MedisProject Photography. They will come to your villa for a family or couples photoshoot against the beautiful backdrop of the Tuscan hillside.
Ask your Destination Concierge to schedule a cooking class with Touch Florence, a true Italian experience. Begin with a market visit and then prepare your purchases under the expert guidance of an executive chef.s.
For more information about vacationing in this destination, contact your Care team.
Tuscan cuisine is about what's fresh, and the best stuff ripens between October and March: olives, big red wines, porcini mushrooms, black truffles, chestnuts … and with winter being hunting season, even the wild boar is fresh.
A "frantoio" is where small grove owners bring olives to be pressed into oil. Not particularly beautiful, and not necessarily popular sites, they can be fun, so stop and ask to see the operation; try the one at Via di Martiena 2 in Montepulciano.
Just outside Florence is a luxury outlet center with the unfortunate name of The Mall. With shops from McQueen to Pucci, there are amazing bargains. It's open seven days a week, which can be a blessing when the rest of Italy is closed.
Tuscany is leather country. If you want the good stuff, skip the leather market in Florence and instead head to Arti Minori in Siena (53 Via Camollia), where there are made-to-measure men's shoes and women's purses to die for.
Unlike other wine regions, Italy is not known for opening its vineyards' tasting rooms like stores. For many you'll need a reservation, while others are closed to the public entirely. It's best to take an organized wine tasting tour.
The Adventure Park Il Gigante delivers family fun right in Tuscany. Fly through the air on zip lines, cross suspended bridges and balance on mid-air catwalks. Kids will love the Tarzan jumps, tight ropes, a flying skateboard and climbing walls.
There's no better place in the world to take part in the savory celebration of food and wine than Tuscany, Italy. Forever recognized as one of the world's most aesthetically pleasing landscapes, the region offers old world, organic wineries, acres of olive groves and beautiful hill towns at every turn. With Inspirato, members are treated to private wine pairings, intimate cooking classes with Michelin star rated chefs and a host of expertly curated side trips to quaint villages and Renaissance-era cities.
Nothing short of perfected comfort, the weather in Tuscany is mild - with the seasons accentuated by everything you desire for your visit. The long summers, which are ideal for touring the region's wineries and olive groves, will win your heart. Hike among the Tuscan sunlit trails, explore ancient towns in the cool of the winter and bask in the quiet moonlight on the balcony of your residence.