Tuscany Walking
Ancient Footpaths North of Siena
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. Stand under towering sunflowers. Taste the Chianti and the olive oil on bread toasted in a stone fireplace. There is no better - or closer - way to truly experience Tuscany.
- Unforgettable rambles though Chianti's hills and vineyards
- Fresh Tuscan cuisine and luxurious historic lodging
- Explore classic medieval hill towns including Radda and Vertine
- Join a wine expert for a tasting of Brunello di Montalcino and other vintages
- Tuscan cooking lesson with a local chef
The Day-to-Day Itinerary
Day 1 Unforgettable rambles though Chianti's hills and vineyards 
Discover the nuances of Tuscan olive oils and honey during a private visit to Badia a Coltibuono ("Abbey of the Good Harvest"), founded a thousand years ago Oak trees and grapevines line the walk to Gaiole in Chianti.
Day 2 Tuscan cooking lesson with a local chef - learn the finer points of piatti tipici toscani (typical Tuscan dishes) A guided tour through ancient passageways reveals historic Radda in Chianti, a center of Chianti Classico wine production.
Day 3 Explore archetypal medieval hill towns including Vertine, a fortified hamlet perched well off the beaten path Savor lunch by Castello di Meleto Ramble through pristine vineyards and pine forest in the heart of the Chianti Classico region en route to Castello di Tornano, former residence of the Ricasoli family.
Days 4-6 Taste Brunello di Montalcino and other vintages with a local expert Set out toward Castello di Brolio, home of the original Chianti Classico recipe, while taking in views of distant Siena along the way Enjoy an evening wine tasting and wander in Siena's handsome medieval center Stroll to the quaint village of San Sano for lunch in the sleepy piazzetta 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
Premiere Inns
Castello di Spaltenna
Gaiole in Chianti (2 nights) In the heart of Chianti Classico, this impressive restored feudal settlement dates back 1,000 years and is surrounded by vineyards and woods. (pool)
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 Scopeto
Vagliagli (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)
Tuscany Walking
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 |
|---|---|---|---|
| 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 |
Daily Mileage Options & Cumulative Elevation Gain
Day 1
- Level 2
1 Route Option Available
- 6.5 miles
- 230 feet elevation gain
Day 2
- Level 1 2 Route Options Available
- Guided Walking 1.5 hours
- 2.9, 4.5 miles
- 430 - 550 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
- 850 - 1360 feet elevation gain
Day 6
- Level 1 2 Route Options Available
- 1.7, 4 miles
- 300 - 630 feet elevation gain