Tuscany & Umbria Insider
Ageless scenery, rich history, and stellar wine and cuisine make Tuscany and Umbria ideal destinations for culturally curious travelers. This region is a second home for us: Backroads has had an office in Tuscany for 20 years. We’ve also built relationships with local people who know the area intimately, who can peel back its layers and reveal its passionate heart. We’re excited to offer this trip filled with special events and encounters—from a behind-the-scenes exploration of Florence to fun-filled cooking classes—giving you the most in-depth Italian experience possible. You’ll meet artists, chefs and historians who are happy to tell you their stories and share their expertise. And when you return home, don’t be surprised if you’ve become part of an extended famiglia internazionale!
Timeless Hill Towns
Within their stone ramparts, the proud hill towns of Tuscany and Umbria offer a blissful escape from the 21st century. Discover the essence of Italy as we introduce you to a few of our favorites: In Todi, linger in the Piazza del Popolo, one of the prettiest squares in Italy. And uncover Assisi with guide Rosella Fiorucci, who knows Saint Francis’ hometown come la sua tasca (like her own pocket).
Buon appetito!
Something about Italian cuisine appeals to the soul. Straightforward and honest, it celebrates fresh ingredients prepared with minimal manipulation – proud but not boastful. A glass of red wine, thinly sliced prosciutto, warm bruschetta, some aged parmigiano reggiano splashed with balsamic vinegar – it’s habit forming! Discover the joys of the Italian table in true Backroads style, with a cooking demonstration and hands-on lesson, an exclusive chocolate factory tour, superb picnics and unforgettable dinners.
Sensational Siena
Fall in love with Siena as you explore the city’s handsome medieval center with local guide Laura Antoni. Learn about its 17 fiercely competitive contrade (districts). Admire the black-and-white striped façade and exuberant ornamentation of the Duomo. Linger at the Piazza del Campo and imagine how it looks twice a year – filled with dirt, galloping horses and frenzied spectators – during the city’s famous Palio bareback race.
"The sun of Italy in a bottle"
Even if you’re new to the pleasures of the vine, this trip is sure to unleash your inner oenophile. At Le Pozze di Lecchi, enjoy a private tasting of Tuscan wines such as Chianti Classico. Down south on a lofty Umbrian hilltop is Orvieto, where you can try white wines that have been praised by artists, poets and nobles since the Middle Ages. Though the dry version predominates, also be sure to taste the semisweet abboccato variety. Cin cin!
Umbrian Eye Candy
The origin of Italian ceramics dates back to the Etruscans, but it was not until the Renaissance that the art of majolica reached its full splendor, with brilliant colors and refined decorations. In Deruta, one of the world’s oldest ceramics centers, you can paint your own piece during our private class at a prestigious regional pottery producer.
SOOTHING STYLE : Casual Inns
Le Pozze di Lecchi (2 nights): Originally a 15th-century mill, this charming small hotel is set amid wooded hills in the heart of Chianti and welcomes you with a swimming pool, sauna and massage service.
Hotel San Simeone (1 night): A stunning panorama of the Val d’Orcia and an inviting swimming pool are yours to enjoy at this beautifully restored hotel.
Fattoria di Vibio (2 nights): Offering a relaxed and homey ambience, this working farm in the middle of the countryside features two swimming pools, a spa with massage service and an excellent restaurant.
Reserve early for the best available price. Prices may change during the course of the year--if they do change, the best prices are available earlier. Once you book your trip, your price is guaranteed.
Trip praise
Backroads is really excited to add our latest way to explore the world - Insider Trips - to our award-winning biking, hiking and multisport vacations. These are experiences you cannot have behind the wheel of a car, or on a train or a tour bus, or in a few excursions from a cruise ship or a secluded resort.- Backroads President and Founder