Tuscany Walking
Exploring Ancient Footpaths North of Siena
As you make your way down a footpath strung along a wide-open hillside, you’ll understand why Tuscany has captivated writers and visual artists for centuries. Broad wheat fields and tidy vineyards greet cypress-rimmed hill towns, and fertile valleys lie bathed in golden sunlight. Discover the simple charms and exquisite details of Tuscany as you stroll through this region rich in history, culture and natural splendor.
Trip Planning Links
- Unforgettable rambles though Chianti’s hills and vineyards
- Fresh Tuscan cuisine and historic lodging
- Explore classic medieval hill towns including Radda and Greve
- Taste Brunello di Montalcino and other vintages with an expert
- Join a local chef for lessons in pizza- and gelato-making
The Day-to-Day Itinerary
Days 1-2 PANZANO in Chianti
Get to know the hilltop village of Panzano on a walk through ancient vineyards to an 11th-century Romanesque church Stroll through the charming hamlet of Montefioralle on the way to Greve in Chianti, which went up in flames in 1325, but rose from the ashes a century later to become one of the most important wine centers in the Chianti region 
Oenophiles will especially enjoy our wine tasting with longtime Backroads friend Fabrizio Ferucci.
Day 3 GAIOLE in Chianti
Wander the quaint centro storico of Radda in Chianti.
Days 4-6 Monteriggioni
After a short shuttle to Radda in Chianti, walk ancient paths to Castellina in Chianti, a crown jewel of this prestigious wine region Savor an exclusive wine tasting at an enoteca en route Spend the evening dining and strolling in Siena, Italy's best-preserved medieval city From Abbadia a Isola, hike among the hills of the Montagnola Senese, located along the pilgrimage route between Spain and Jerusalem Climb to the hilltop village of Monteriggioni where Dante once roamed, likening its 13 towers to giants in his Divine Comedy.
- 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!
An amazing experience. Our leaders were terrific. The trip was well-planned and well-executed. The days were so full I could hardly absorb it all. The countryside, the views, the food, the wine, the delightful company of so many interesting people and the feeling that we were able to experience Tuscany at a very real and personal level made for memories for a lifetime!- Indianapolis, IN More about this Trip All Guest Reviews
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Tuscany Walking
ECHOES OF THE PAST: Casual Inns
Villa le Barone
PANZANO in Chianti (2 nights)
Owned by the same family since the 1500s, this former manor house in the heart of Chianti features a swimming pool, tennis courts and terraces surrounded by rose gardens.
Albergo l'ULTIMO MULINO
Gaiole in Chianti (1 night) At this renovated medieval grain mill, the reservoir that once powered the mill now serves as a beautiful lap pool with vistas of lush vineyards.
Castel Bigozzi
Monteriggioni (2 nights)
Once a 13th-century castle, this hotel offers a swimming pool and a peaceful setting in the Sienese hills.
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 1 2 Route Options Available
- 3.2, 4.7 miles
- 290 - 420 feet elevation gain
Day 2
- Levels 1 to 2 3 Route Options Available
- 3.7, 5.2, 6.1 miles
- 600 - 900 feet elevation gain
Day 3
- Levels 2 to 3 2 Route Options Available
- 5.3, 7.9 miles
- 300 - 500 feet elevation gain
Day 4
- Levels 1 to 2 2 Route Options Available
- 3.2, 6.6 miles
- 200 - 500 feet elevation gain
Day 5
- Levels 2 to 3 2 Route Options Available
- 5.7, 8 miles
- 1100 - 1300 feet elevation gain
Day 6
- Level 1 1 Route Option Available
- 2.5 miles
- 500 feet elevation gain