Tuscany Walking & Hiking
- Unforgettable rambles though Chianti's hills and vineyards
- 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 7am–5pm,PST
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Ancient Footpaths in Bella Toscana
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 the Monte Oliveto Maggiore an important stop on the ancient Via Francigena pilgrimage route Amble through pristine vineyards and pine forest en route to Radda in Chianti, the center of Chianti Classico wine country Learn 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 inspired Renaissance artists Hike hilly roads through vineyards and oak forests and along ridges offering sweeping views Follow a quiet route up to the majestic neo-Gothic Castello di Brolio, where Baron Bettino Ricasoli formulated the modern method of producing Chianti Classico wine in the 19th century The fall offers the chance to revel in beautiful colors and 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.- 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.- Davis, CA
Our leaders were incredible. They cared for our every need/desire while ensuring our safety. That translated to our group and by the time we were on the bus in Florence (on day 1!) we were like family. That cohesiveness grew during our hikes and experiences. It was truly a magical week! Thank you and special, heartfelt thanks, to our amazing leaders.
Premiere Inns
Castello di Velona
Montalcino (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)
Palazzo Leopoldo
Radda in Chianti (1 night) Located in the heart of the Chianti region, this 14th-century manor house features spacious guest rooms with original frescoes. (spa)
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)
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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 | ||||||||||
| Day | EASYGOING | ACTIVE | AVID | |||||||
|---|---|---|---|---|---|---|---|---|---|---|
| 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 | 4.3* | 100 | 5.7 | 200 | ||||||
| 2 | 3.4* | 200 | 4.8* | 800 | 8.7* | 900 | ||||
| 3 | 4.0* | 500 | 5.0* | 500 | 6.9 | 1800 | ||||
| 4 | 4.5* | 500 | 5.7* | 500 | 7.4* | 800 | ||||
| 9.2* | 1300 | |||||||||
| 5 | 4.0* | 600 | 8.6* | 900 | 10.4 | 1100 | ||||
| 6 | 2.9 | 200 | ||||||||
The terrain on this trip includes vineyard footpaths and wooded trails.
* Includes a shuttle
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For 34 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.
