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TRIP NOTES

All meals included except 1 lunch and 1 dinner.

Cancellation Policy

Cancellation fees may vary based upon departure date. Please call our expert Trip Consultants at (800) GO-ACTIVE (462-2848) for more information.

Meet / Depart

Florence, Italy/Orvieto, Italy

Special Interest

Cooking, Culture & History, Fine Wine & Cuisine, Natural Beauty &/or Wildlife

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Tuscany Italy Insider
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Tuscany Family Insider

From Classic Tuscany to the Green Heart of Italy

Ageless scenery, rich history and, of course, stellar wine and cuisine make Tuscany and Umbria ideal destinations for travelers of all ages. 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 and your family 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!

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Timeless Hill Towns

Within their stone ramparts, the proud hill towns of Tuscany and Umbria offer a blissful escape from the 21st century. With local expert Giovanni Adreani, explore Cortona from its Etruscan tombs to its historic neighborhoods. 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, 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 the fine 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 and your family can paint your own pieces during our private class at a prestigious regional pottery producer.

Jeff Cantarutti, Our Man in Chianti

Jeff draws on a passionate Italian heritage to create unforgettable Insider experiences: "My father was twice knighted by Italy's government for his efforts in promoting Italian culture in the U.S. And I can show up at the homes of my Italian cousins anytime." Now our Regional Manager in Italy, Jeff has led Tuscan trips since 1994. "From the first moment, I knew I'd be coming back forever. And thanks to the local friendships I've cultivated over the years, our trips have an authenticity that can't be matched."

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.
Tom Hale - Backroads President and Founder

For more than 29 years, Backroads has been perfecting the art of active travel. We are the Tuscany tour experts. For Insider tours in Europe Italy, trust our in-depth connections. To see all our Europe Italy Insider tours click here. For our selection of award-winning Europe Italy biking tours click here. For our selection of award-winning Europe Italy walking and hiking tours click here. For our selection of award-winning Europe Italy multisport tours click here.

Tuscany Family Insider

SOOTHING STYLE : Casual Inns

Le Pozze di Lecchi

Gaiole in Chianti (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

Rocca d'Orcia (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

Montecastello 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.

Tuscany Family Insider Tuscany Family Insider

Le Pozze di Lecchi

You are viewing the Family Casual Inns version of this trip.
View the Family Premiere Inns Itineraries.

View the Classic Premiere Inns , Classic Casual Inns Itineraries.

Tuscany Family Insider

Route Rating

Daily Mileage Options & Cumulative Elevation Gain

Tuscany Family Insider Tuscany Family Insider

Trips For All Abilities

Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. We know your pace may vary from one day to the next-and your traveling companion's may differ somewhat from yours. So we present a range of mileage options, and each day you decide exactly what and how much you want to do.

Activity Level Average Time Average Distance
    Biking Walking
& Hiking
1 2-3
hours
10-20
miles
2-5
miles
2 2-4
hours
21-30
miles
5-7
miles
3 3-5
hours
31-40
miles
7-9
miles
4 4-6
hours
41-55
miles
9-11
miles
5 5-7+
hours
56-75+
miles
11-13+
miles