Tuscany Biking
A Taste of Tuscany in Chianti Classico
Tuscany's vibrant, colorful landscape is a magical place for bicycling. In spring, fields are aflame with red poppies, and come fall, the air is rich with scents of thyme, rosemary and fennel. Tomatoes hang heavy in gardens and vineyards burst with purple grapes. Join Backroads and bike the same hills that draw local cyclists, explore medieval villages that have seen their share of war and peace, and enjoy the cultural and culinary wealth that northern and southern Tuscany have to offer. Savor pecorino cheese, homemade pasta, fruity olive oils and celebrated Chianti and Brunello di Montalcino wines. Discover the region’s irresistible combination of natural beauty, Renaissance art and architecture, and friendly people.
- A quintessential Tuscan experience from south to north
- Explore some of the region’s most celebrated towns, including Montepulciano, Pienza, Montalcino, Siena and Radda in Chianti
- After a dinner of local specialties, taste fine wines with a sommelier
- Pedal rolling hills past Brunello, Chianti Classico and Sangiovese vineyards
- Relax at day’s end in cozy historic hotels, all with swimming pools
The Day-to-Day Itinerary
Days 1-2 Castiglione d'Orcia
Meet in Florence 
Enjoy a picnic of Tuscan treats at an organic farm that produces olive oil, butter, salami and prosciutto From the flanks of Mount Amiata, warm up your legs on a rolling route through the countryside 
Get to know southern Tuscany en route to the Roman thermal baths in Bagno Vignoni Wander around Montepulciano, chock-full of hidden squares, Renaissance palaces and ornate churches Stop at an enoteca to experience the region's claim to fame, Vino Nobile di Montepulciano In Pienza, sample delicious pecorino (sheep’s milk) cheese.
Day 3 Castelnuovo Berardenga
Today’s route takes you from the open, undulating hills of southern Tuscany to the wooded, olive tree-lined roads of the north In Montalcino, climb the tower of San Martino for panoramic views of the Val d’Orcia including, on a clear day, Siena Indulge in a picnic feast beneath the arches of the Monte Oliveto Maggiore abbey.
Days 4-6 San Leonino
Pedal through some of Chianti’s most beloved towns, such as Gaiole, Radda and Castellina Author Dario Castagno joins us for an engaging Q & A session Explore Siena on your own Spin past Sangiovese vineyards to Greve, where you can sample local wines or sip a cappuccino in the lively piazza Shuttle to Florence.
- 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.
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Look at what other guests are saying about this trip!
Magnifico! I can't think of a better way to immerse myself in the Italian culture in the Tuscany region than with Backroads. The scenery, wonderful local towns/bastions, the food (off the charts), gracious people, the great leaders and people on the trip exceeded my expectations once again. We ate like kings (peasants technically), stayed in wonderful accommodations complete with their own great views, sampled the wine like royalty, the pizza and sorbet we gorged on were out of this world, and we biked some of the most beautiful countryside I have traveled. Time will tell where Backroads will lead me next...- Annapolis, MD More about this Trip All Guest Reviews
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Tuscany Biking
MEDIEVAL MODERNITY: Casual Inns
Osteria dell'Orcia
Castiglione d'Orcia (2 nights) Set in the Tuscan countryside, this post station from the 1600s has been lovingly restored into a beautiful four-star hotel.
Villa Curina Resort
Castelnuovo Berardenga (1 night) A restored 16th-century villa, this resort features traditional and modern furnishings, a large swimming pool, a solarium and tennis court.
Belvedere di San Leonino
San Leonino (2 nights) Surrounded by vineyards and cypress trees, this hotel offers rustic Tuscan-style furnishings, a beautiful garden and panoramic views of Siena.
Tuscany Biking
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 |
|---|---|---|---|
| 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
- 21 miles
- 1200 feet elevation gain
Day 2
- Levels 1 to 5 4 Route Options Available
- 20, 35, 48, 60 miles
- 1400 - 4700 feet elevation gain
Day 3
- Levels 2 to 5 3 Route Options Available
- 30, 53, 74 miles
- 2800 - 4900 feet elevation gain
Day 4
- Levels 2 to 3 3 Route Options Available
- 26, 38, 40 miles
- 2700 - 3800 feet elevation gain
Day 5
- Levels 2 to 5 3 Route Options Available
- 29, 46, 59 miles
- 1900 - 5000 feet elevation gain
Day 6
- Level 1 1 Route Option Available
- 12 miles
- 800 feet elevation gain