Tuscany Walking
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 cuisine and wines. Benvenuti in Toscana!
Days 1-2 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 Toscana Mia cooking school.
Day 3 San Felice
Leaving Gaiole, stroll the strade bianche (unpaved trails) past ancient vineyards and gnarled olive trees Explore the tiny fortified hamlet of Vertine, perched well off the beaten path Enjoy lunch at the foothill of Castello di Meleto 
Visit Castello di Brolio, the region's most famous castle, where the original recipe for Chianti Classico was formulated.
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 grand picnic in the countryside Swirl, sniff and sample fine vintages at a wine tasting in Siena Stroll to Fattoria Dievole, a vineyard in Vagliagli, lunch the quaint Chianti hamlet of San Sano, or relax in luxury at our picture-perfect hotel.
DISTINCTIVE ESTATES: Premiere Inns
Castello di Spaltenna (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.
Borgo San Felice (1 night): This Relais & Châteaux-member hotel is a beautifully restored medieval Tuscan hamlet with a swimming pool, tennis courts and a setting amid vineyards, olive groves and oak-covered hills.
Relais Borgo Scopeto (2 nights): This traditional elegant Tuscan estate, nestled among vineyards and olive trees and overlooking Siena, offers two swimming pools, a restaurant, and contemporary guest rooms with antiques.
Daily Mileage Options & Cumulative Elevation Gain
Day 1
- Level 1 to 3 1 Route Option Available
- 6.2 miles
- 150 feet elevation gain
Day 2
- Levels 1 to 3 2 Route Options Available
- 2.9, 4.5 miles
- 500 - 1500 feet elevation gain
- Walking Tour 1 hour
Day 3
- Levels 1 to 2 2 Route Options Available
- 4.5, 5.7 miles
- 0 - 500 feet elevation gain
Day 4
- Levels 2 to 4 2 Route Options Available
- 6.3, 10.8 miles
- 1000 - 2500 feet elevation gain
Day 5
- Levels 1 to 2 2 Route Options Available
- 3, 5.2 miles
- 0 - 1000 feet elevation gain
Day 6
- Level 1 1 Route Option Available
- 2.2 miles
- 0 - 1000 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 |
2008 DATES
CLASSIC TRIPS
- 9/14-19Price: $4298 pp dbl. occ., (+ $1350 for sgl. occ.)
The trip you have selected is different from the one displayed. Here's how:
Hotel Rotation: We will now stay at Castello di Tornano for Day 3 and the Villa la Massa on Days 4 & 5.
Some activities may vary due to the hotel rotation. Contact your trip consultant for more information. - 10/5-10Price: $4298 pp dbl. occ., (+ $1350 for sgl. occ.)
2009 DATES
CLASSIC TRIPS
- 5/17-22Price: $4498 pp dbl. occ., (+ $1480 for sgl. occ.)
- 5/31-6/5Price: $4498 pp dbl. occ., (+ $1480 for sgl. occ.)
- 9/13-18Price: $4498 pp dbl. occ., (+ $1480 for sgl. occ.)
- 10/4-9Price: $4498 pp dbl. occ., (+ $1480 for sgl. occ.)
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
Our leaders were fabulous. The itinerary and experiences could not have been betterI 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
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