Tuscany Walking
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.
Days 1-2 PANZANO in Chianti
Meet in Florence 
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 and olive oil aficionados will especially enjoy visiting a local enoteca, where more than 100 wines and a variety of oils are available for tasting.
Day 3 GAIOLE in Chianti
Soak up beautiful views along the scenic ridgeline of the Monti del Chianti en route to charming Volpaia, an ancient village-turned-winery 
Wander the quaint centro storico of Radda in Chianti Learn the art of pizza-making under the tutelage of our Tuscan friend Lele Vitale Cap off the afternoon with homemade gelato and a Tuscan sunset at Lele’s house.
Days 4-6 SAN LEONINO
After a short shuttle to Radda, walk ancient paths to Castellina in Chianti, a crown jewel of this prestigious wine region Savor an exclusive wine tasting in Castellina 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 and soak in the vista from one of its 13 towers.
ECHOES OF THE PAST: Casual Inns
Relais Fattoria Valle (2 nights): Formerly a private residence, this restored hotel presents antique furnishings, a swimming pool, cozy restaurant and spectacular view.
ALBERGO L'ULTIMO MULINO (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.
BELVEDERE DI SAN LEONINO (2 nights): Surrounded by vineyards and cypress trees, this hotel features a swimming pool, rustic Tuscan-style furnishings and a panoramic view of Siena.
Daily Mileage Options & Cumulative Elevation Gain
Day 1
- Level 1 2 Route Options Available
- 3.2, 4.7 miles
- 0 - 500 feet elevation gain
Day 2
- Levels 1 to 2 3 Route Options Available
- 3.6, 5.2, 6 miles
- 500 - 1000 feet elevation gain
Day 3
- Levels 1 to 3 2 Route Options Available
- 5.3, 7.9 miles
- 0 - 500 feet elevation gain
Day 4
- Levels 1 to 3 2 Route Options Available
- 3.2, 8 miles
- 0 - 500 feet elevation gain
Day 5
- Levels 2 to 3 2 Route Options Available
- 5.7, 8 miles
- 1000 - 1500 feet elevation gain
Day 6
- Level 1 1 Route Option Available
- 3 miles
- 500 feet elevation gain
Trips 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 | Average Distance | |
|---|---|---|---|
| Biking | Walking & Hiking | ||
| Level 1 | 2-3 hours | 10-20 mile | 2-5 miles |
| Level 2 | 2-4 hours | 21-30 miles | 5-7 miles |
| Level 3 | 3-5 hours | 31-40 miles | 7-9 miles |
| Level 4 | 4-6 hours | 41-55 miles | 9-11 miles |
| Level 5 | 5-7+ hours | 56-75+ miles | 11-13+ miles |
2009 DATES
CLASSIC TRIPS
- 5/24-29Price: $3198 pp dbl. occ., (+ $860 for sgl. occ.)
The trip you have selected is different from the one displayed. Here's how:
Early Booking Promotion: $500 Savings per Couple currently available for this departure.
Call today to book and save. Limited time offer. - 9/20-25Price: $3198 pp dbl. occ., (+ $860 for sgl. occ.)
The trip you have selected is different from the one displayed. Here's how:
On Days 4 & 5 we stay at Hotel Colle Etrusco Salivolpi, located in the heart of the Chianti Classico region.
Reserve early for the best available price. Prices may change during the course of the year--if they do change, the best prices are available earlier. Once you book your trip, your price is guaranteed.
Guest Trip Reviews
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
Great trip. Our leaders were very flexible, good-natured, and accommodating. They got us off the beaten path in an area that can be very touristy. We especially enjoyed the pizza & gelato experience with Lele. Great job with the local flavor aspect of the trip.- Toano, VA
To be honest, Backroads far exceeded my expectations with the trip. I'm not usually keen on group trips. However, I was impressed with both the quality and abilities of the leaders, the pre-hike prep and route raps, the number and type of group activities arranged, and the quality of the accommodations. I will definitely look for another Backroads trip to take. Thank you.- Toronto, ON
This trip exceeded my expectations. I had no idea there would be so much flexibility and that everything would run so smoothly.- Atlanta, GA
Backroads is an awesome company and your leaders are top notch. It really appeared they received support from the company so in turn they could provide great support for the guests. The inns were gorgeous, the food fabulous, and the hiking routes terrific.- Decatur, GA