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Tuscany Walking & Hiking Tour

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Trip Highlights
  • Unforgettable rambles though the Chianti Classico wine region, blanketed with vineyards and olive orchards
  • Enjoy a warm welcome at Agriturismo Il Rigo for an authentic pasta making demonstration
  • Discover the World Heritage site of Siena, where medieval architecture meets contemporary culture
  • Explore classic hill towns including Pienza, Radda, Gaiole, Panzano and Greve
  • Join a wine expert to sample a variety of the San Felice estate wines and other regional vintages

Call 800-462-2848, Every day 6am-6pm,PST

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Ancient Footpaths in Medieval Italy

Tuscany must be experienced up close. Taste the Brunello. See the bread toasted in a stone fireplace, glistening with freshly pressed olive oil. Look out over the Arno River winding through the patchwork landscape. Walk on the gently sloping hills of the Val d'Orcia to ancient hilltop towns. Smell the wild cypress and rosemary. Stroll through the vineyards and olive groves of Chianti. Let your eyes linger on timeless villas and imagine the possibilities. There is no better—or closer—way to experience Tuscany.


Days 1-2 From the hamlet of Monticchiello, discover the picture-perfect landscape of the Val d'Orcia Have a look around Renaissance-style Pienza, Pope Pius II's utopian village, perhaps stopping to try the superb local pecorino cheese  In springtime, the surrounding hills provide a backdrop of emerald green, while in the fall, hay bales turn the landscape a brilliant shade of gold  Sample a variety of regional vintages at our hotel's exclusive tasting room Follow a quiet route up to the majestic Castello di Brolio, where Baron Bettino Ricasoli formulated the modern method of producing Chianti Classico in the 19th century.

Days 3-4 Explore the heart of the Zona del Chianti  From Radda, amble through pristine vineyards and pine forests en route to Gaiole in Chianti, the center of Chianti Classico wine country  Learn the secrets of Tuscan cuisine at an exclusive cooking demonstration  Head into the Chianti countryside and walk from one castle to the next Take a break in Vertine's cozy piazzetta to enjoy a cappuccino and observe the friendly pace of local life  In Panzano, learn about ancient recipes and the region's finest meats at Dario Cecchini's renowned macelleria.

Days 5-6 In the Elsa River valley, get a feel for the Colli Fiorentini (Florentine Hills), where expansive vineyards and wildflower fields greet you at every turn Savor Michelin-starred cuisine inspired by Tuscan traditions and flavors  Stride along the crest to Montefioralle, birthplace of Amerigo Vespucci Hike hilly roads through oak forests and along ridges offering sweeping views that once inspired Renaissance artists.

Premiere Inns

La Bandita Townhouse
La Bandita Townhouse

Pienza (1 night) This luxury boutique hotel, tucked inside a Renaissance-era palazzo where nuns lived for over 500 years, is refreshingly modern inside. (pool)

Borgo San Felice
Borgo San Felice

San Felice (2 nights) Described by the Hideaway Report as an "enchanting resort enclave set within a restored medieval hamlet fringed by olive groves and vineyards in the Chianti Classico region." A Relais & Châteaux member. (pool, spa, tennis)

Castello del Nero
Castello del Nero

Tavarnelle Val di Pesa (2 nights) A castle with a Michelin-starred restaurant steeped in Tuscan charm and situated on a hilltop overlooking rolling vineyards and olive orchards in the Colli Fiorentini. (pool, spa)  

Guest Reviews About This Trip

Our leaders were fabulous. The itinerary and experiences could not have been better - I can't say enough to praise this trip! Having spent a lot of time in Chianti previously, I still learned, saw and experienced new things in unusual ways. My two friends with whom I traveled feel exactly the same way. It was perfect.
Marilyn R.- Scarsdale, NY
Taking a Backroads trip is like enjoying the sweetest part of the watermelon, the planners and trip leaders trim away everything but the sweetest core of the trip. They worry about the logistics, the problem solving, so that as a guest, the most you worry about is what to order at dinner and how far to go on each daily option.
Jeff Tanji- Davis, CA
We were impressed with the comfortableness with the people, the warmth and helpfulness of the guides, the flexibility of the itinerary, the good mix of planned time and free time, the well set-up walks that were incrementally longer each day so we could "build up" a bit, the loveliness of most of the lodgings, the firsthand view of the people of Italy, and of course the beauty of the country itself. I met my personal goal of doing all of the walking, and enjoyed every minute of it. I have a lasting image of our guide, catching the attention of two boys at the side of the road who were watching us all traipse through his village. He engaged them in conversation, told them who we were, asked them about the soccer ball they were playing with, and talked them into showing us their "moves." With that little dialogue, we moved from being strangers passing through to new friends visiting with local kids. I valued a lot of the personal interaction which the guides sought out with the Italian people everywhere we went. That helped us be more a part of the country. My other favorite memory is hiking on some of the back roads up through the vineyards to a place where the countryside was laid out before us like a quilt, made up of squares of vineyards, olive groves, and forested patches. Beautiful, and memorable.
Susan Mosher- Chicago, IL

Trip Dates & Prices

Please click on a date below for specific pricing and possible itinerary variations.

2015 September
2015 October
2016 May
2016 June
2016 September
2016 October

Don't see your ideal travel date? Call us at 800-462-2848 for Private Trip date availability.

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This Trip Is Rated Level 1-4

Routes 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.

Daily Route Options
Level 1 Level 2 Level 3 Level 4 Level 5
miles feet gain miles feet gain miles feet gain miles feet gain miles feet gain
1 3* 400 4* 600
2 3* 300 4* 200 6* 500
3 6* 500 8* 800 10* 1000
4 4 500 9 600
5 3 600 4 900 8 1500
6 3 300

The terrain on this trip includes vineyard footpaths and wooded trails.

* Includes a shuttle

Private Trips Options & Pricing

Gather your favorite people to share a Backroads adventure on a ready-to-book Private Trip - featuring all the legendary Backroads hallmarks from expert leaders to unforgettable activities.

You can pick from a large selection of dates for your group of 8 or more. Call us for date availability.

If your party has fewer than 8 guests, or if your preferred date is not available, we'll create a departure just for you.

Pricing for Private Trips (prices may vary based on departure date)


2 - 3 guests from $7,198 pp dbl. occ. 8 - 9 guests from $5,498 pp dbl. occ.
4 - 5 guests from $6,198 pp dbl. occ. 10 - 11 guests from $4,898 pp dbl. occ.
6 - 7 guests from $5,698 pp dbl. occ. 12 or more guests from $4,598 pp dbl. occ.


2 - 3 guests from $6,998 pp dbl. occ. 8 - 9 guests from $5,398 pp dbl. occ.
4 - 5 guests from $5,998 pp dbl. occ. 10 - 11 guests from $4,898 pp dbl. occ.
6 - 7 guests from $5,598 pp dbl. occ. 12 or more guests from $4,598 pp dbl. occ.

All Private Singles-Solos trips require a minimum of 16 guests.

For 36 years, Backroads has been perfecting the art of active travel. We are the Tuscany tour experts. See our award-winning Europe Italy walking tours and hiking tours, Europe Italy biking tours and Europe Italy multisport tours.

Walking & Hiking

Premiere Inns
Route Rating

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Florence, Italy

Detailed Itinerary

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Trip Notes

All meals included except 1 lunch, 1 dinner

Recommended Reads

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