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Tuscany Walking & Hiking Tour

Route Rating
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Trip Highlights
  • Unforgettable rambles though Chianti's hills and vineyards
  • Visit Monte Oliveto Maggiore, a Benedictine abbey founded in 1313
  • Fresh Tuscan cuisine and luxurious historic lodging
  • Explore classic medieval hill towns including Pienza and Vertine
  • Join a wine expert for a tasting of Brunello di Montalcino and other vintages

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

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Ancient Footpaths in Medieval Italy

It just makes sense really. The closer you get to something, the richer your experience. Fly over Tuscany and you may see Florence as a cluster of red clay roofs. Maybe you see the Arno River winding through the patchwork landscape. Take a bus, you get an idea of the hills and scenery. But stroll past its vineyards and olive groves. Smell the cypress and rosemary. Stand in the shade of oak trees. Taste the Brunello and the olive oil on bread toasted in a stone fireplace. There is no better - or closer - way to truly experience Tuscany.

Days 1-2 Abbey of Sant'Antimo, a former Benedictine monastery dating back to the late 18th century  Enjoy unforgettable views of Tuscany from the medieval hamlet of Castelnuovo dell'Abate  The Val d'Orcia invites a wander  Explore the architectural treasures in Pienza and sample its renowned pecorino cheese  Discover world-famous Brunello wine in Montalcino.

Days 3-4 Visit and picnic at Monte Oliveto Maggiore, an important abbey on the ancient Via Francigena pilgrimage route  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  Amble through pristine vineyards and pine forest en route to Radda 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 Gaiole's cozy piazzetta to enjoy a cappuccino and observe the friendly pace of local life.

Days 5-6 Immerse yourself in the landscape that once inspired Renaissance artists  Hike hilly roads through vineyards and oak forests and along ridges offering sweeping views  Spring regales you with fields of fiery red poppies while autumn offers the chance to watch the grape harvest.

Guests 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

Premiere Inns

Castello di Velona
Castello di Velona

Castelnuovo dell'Abate (2 nights) This 11th-century fortress features terra-cotta floors, individually decorated rooms and stunning views of the Val d'Orcia. A Small Luxury Hotels of the World member. (pool, spa)

Relais Borgo San Felice
Relais Borgo San Felice

San Felice (1 night) 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)

Relais Borgo Scopeto
Relais Borgo Scopeto

Vagliagli (2 nights) Owned by the Sienese cathedral in the 1200s, this elegant estate offers panoramic views of Siena and the Mangia Tower. (pool, spa)

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 $7,098 pp dbl. occ. 8 - 9 guests $5,198 pp dbl. occ.
4 - 5 guests $6,098 pp dbl. occ. 10 - 11 guests $4,498 pp dbl. occ.
6 - 7 guests $5,498 pp dbl. occ. 12 or more guests $4,198 pp dbl. occ.

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 4* 100 6 200
2 6* 500 9* 800
3 2 100
4* 500
5* 500
4 5* 500 6* 500 7* 800 9* 1300
5 2* 100 5 900 8 1000
6 2* 200
4 200

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

* Includes a shuttle

For 35 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

6 days, 5 nights
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Trip Price**
  • $4,198 to $4,798 pp dbl. occ.
  • (+$1,020 for sgl. occ.)

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Florence, Italy

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