Tuscany Walking
Ancient Footpaths North of Siena
Walk with us in Tuscany and experience the essence of Italy: vineyards and cypress-lined lanes, dramatically perched hill towns, valleys bathed in golden sunlight, celebrated wines, mouthwatering cuisine, unforgettable Renaissance art and architecture, and a warm welcoming people. Make your way along footpaths strung across wide-open hillsides and ramble through picturesque villages that color the landscape. At day's end, settle into some of Tuscany's most charming hotels, and savor hearty local dishes complemented by delectable vintages. Benvenuti in Toscana!
- Unforgettable rambles though Chianti's hills and vineyards
- Fresh Tuscan cuisine and luxurious historic lodging
- Explore classic medieval hill towns including Radda and Vertine
- Taste Brunello di Montalcino and other vintages with a local expert
- Tuscan cooking lesson with local chef
The Day-to-Day Itinerary
Days 1-3 Gaiole in Chianti
Meet in Florence 
Enjoy a private visit to the well-regarded wine- and olive oil-producing estate of Badia a Coltibuono Discover the nuances of fine Tuscan olive oils and honey at a tasting with Coltibuono's resident expert Walk to Gaiole in Chianti, taking in views of Ricasoli family castle ruins Explore medieval passageways and learn about historic Radda in Chianti, the center of Chianti Classico wine production, on a guided tour Learn the finer points of piatti tipici toscani (typical Tuscan dishes) at our cooking school 
Explore the tiny fortified hamlet of Vertine, perched well off the beaten path Enjoy lunch at the foothill of Castello di Meleto Take in views of castles in the surrounding hills, including Castello di Brolio, the region's most famous castle, where the original recipe for Chianti Classico was formulated Hike or shuttle to the magical Castello di Tornano, former residence of the Ricasoli family, and our home for one night.
Days 4-6 Vagliagli
Journey through the vineyard-laden heart of the Chianti Classico region, savoring vistas of distant Siena along the way Feast on local delicacies at a lunch in the countryside Sample excellent vintages at a wine tasting in Siena Stroll to Fattoria Dievole, a vineyard in Vagliagli, and lunch in a quaint Chianti village, or relax in luxury at our picture-perfect hotel.
- Premiere Inns: These lodgings possess both elegance and authentic regional flair.
- Casual Inns: These lodgings are comfortable and appropriate to the area with such characteristics as authenticity, scenic settings and proximity to our activities.
- Deluxe Family Camping: We set up the tents (and take them down), handle every camp chore and perform culinary magic.
Other Trips You Might Like:
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Look at what other guests are saying 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 More about this Trip All Guest Reviews
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Tuscany Walking
DISTINCTIVE ESTATES: Premiere Inns
Castello di Spaltenna
Gaiole in Chianti (2 nights) Surrounded by Chianti hills and vineyards, this impressive restored feudal settlement offers spacious and comfortable guest rooms, indoor and outdoor swimming pools, a sauna, gym and a Turkish bath.
Castello di Tornano
Gaiole in Chianti (1 night) This spectacular 9th-century castle, perched on a hill just outside of Gaiole in Chianti, features charming unique guest rooms, a swimming pool where the castle moat used to be, and in-room massage.
Relais Borgo Scopeto
Vagliagli (2 nights) Overlooking Siena, this traditional and elegant Tuscan estate, nestled among vineyards and olive trees, offers two swimming pools, a restaurant and contemporary guest rooms with antiques.
Tuscany Walking
Daily Mileage Options & Cumulative Elevation Gain
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 | Biking Average | Walking Average |
|---|---|---|---|
| Insider Trips | Explore at a leisurely pace—on village walks, market strolls, art history excursions, hands-on cooking classes and more. | ||
| 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 |
Day 1
- Level 2 1 Route Option Available
- 6.5 miles
- 230 feet elevation gain
Day 2
- Level 1 2 Route Options Available
- Walking Tour 1 hour
- 2.9, 4.5 miles
- 400 - 600 feet elevation gain
Day 3
- Levels 1 to 3 2 Route Options Available
- 4.3, 8 miles
- 600 - 1200 feet elevation gain
Day 4
- Levels 1 to 2 2 Route Options Available
- 3.5, 6 miles
- 600 - 900 feet elevation gain
Day 5
- Levels 1 to 4 2 Route Options Available
- 4.7, 9.9 miles
- 800 - 1400 feet elevation gain
Day 6
- Level 1 2 Route Options Available
- 1.7, 4 miles
- 300 - 700 feet elevation gain