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
Ancient Footpaths in the Heart of Chianti
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 12th century 
Enjoy unforgettable views of Tuscant from the medieval hamlet of Castelnuove dell'Abate
Savor fresh Tuscan cuisine perfectly paired with local wines Discover the Val d'Orcia View the architectural treasures in Pienza Discover Tuscan wine during a tasting at Montalcino.
Days 3-4 Visit San Giovanni d'Asso, known for the huge truffle festival every November Walk through pristine vineyards and pine forest en route to Castello di Tornano, former residence of the Ricasoli family Head into the Chianti countryside on our way to Castello di Meleto Take a break in Vertine’s cozy piazzetta to enjoy a cappuccino and observe the friendly pace of local life.
Days 5-6 Immerse yourself in the heart of the Chianti Classico region We're invited into a private home tucked among award-winning Felsina vineyards for a feast of Tuscan specialties Walk to the quaint village of Castelnuovo Berardenga or relax in luxury at our picture-perfect hotel.
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
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 first-hand 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 Vincent, 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.- Chicago, IL
Premiere Inns
Castello di Velona
Montalcino (2 nights) A medieval fortress turned Renaissance castle is now a refurbished luxury hotel located in the heart of the Chianti region. (pool, spa)
Castello di Tornano
Gaiole in Chianti (1 night) A spectacular 10th-century castle with vineyards, orchards and its own label of wine and grappa. (pool)
Relais Borgo San Felice
San Felice (2 nights) Overlooking Siena and nestled among vineyards and olive trees, this traditional and elegant Tuscan estate was owned by the Sienese cathedral in the 1200s. (pool, spa)
Amalfi Coast Walking & Hiking
From the Sorrentine Peninsula to the Isle of Capri
Classic:
Cinque Terre & Tuscany Walking & Hiking
From the Ligurian Coast to Timeless Tuscany
Classic:
Singles+Solos:
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.
| Activity Level | Average Time | Road Bike Average | Mountain Bike Average* | Walk & Hike Average |
|---|---|---|---|---|
| Level 1 | 2-3 hours | 10-20 miles | 10-15 miles | 2-5 miles |
| Level 2 | 2-4 hours | 21-30 miles | 16-20 miles | 5-7 miles |
| Level 3 | 3-5 hours | 31-40 miles | 21-25 miles | 7-9 miles |
| Level 4 | 4-6 hours | 41-55 miles | 26-30 miles | 9-11 miles |
| Level 5 | 5-7+ hours | 56-75+ miles | 31+ miles | 11-13+ miles |
*Mountain bikes are used in locations where the best riding is on a combination of dirt and paved roads. View trip locations
Daily Mileage Options & Cumulative Elevation Gain
Day 1
- Level 1 1 Route Option Available
- 4.1 miles
- 90 feet elevation gain
Day 2
- Levels 1 to 4 3 Route Options Available
- 3.9, 5.8, 7.5 miles
- 310 - 980 feet elevation gain
Day 3
- Levels 1 to 2 2 Route Options Available
- 4, 5.3 miles
- 440 - 850 feet elevation gain
Day 4
- Levels 1 to 3 3 Route Options Available
- 3.3, 6, 7.3 miles
- 600 - 1200 feet elevation gain
Day 5
- Levels 1 to 4 3 Route Options Available
- 4.5, 6.6, 8.8 miles
- 660 - 1310 feet elevation gain
Day 6
- Level 1 1 Route Option Available
- 2.5 miles
- 330 feet elevation gain
Terrain Description
Vineyard footpaths, wooded trails.More Recommended Trips
Other Trips
For 33 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.
