Tuscany Biking
A Taste of Tuscany in Chianti Classico
To D.H. Lawrence, Tuscany was "the perfect centre of man's universe." Poet Shelley called the region a "paradise for exiles." Dante, a Tuscan native, more than likely called it "divine." You'll undoubtedly conjure up a few superlatives of your own as you pedal from one unbelievable view to the next, gaze in awe at incredible Renaissance art and architecture, and savor delicious pecorino cheese, homemade pasta, fruity olive oils and celebrated Chianti and Brunello di Montalcino wines. Few things in this world live up to the hype. We're delighted to report that everything you've ever heard about Tuscany is true.
- 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
Day 1 A quintessential Tuscan experience from south to north 
Kick things off with 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.
Day 2 Before a dinner of local specialties, taste fine wines with a sommelier
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 Explore some of the region's most celebrated towns, including Siena and Radda in Chianti 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.
Day 4 Spin through rolling hills past Brunello, Chianti Classico and Sangiovese vineyards You'll love visiting some of Chianti's most adored towns, such as Gaiole, Radda and Castellina Author Dario Castagno joins us for an engaging Q & A session Explore Siena on your own.
Days 5-6 Relax at day's end in cozy historic hotels, all with swimming pools Spin past Sangiovese vineyards to Greve, where you can sample local wines or sip a cappuccino in the lively piazza Cap off your trip with a final loop ride from San Leonino to atmospheric Monteriggione.
- 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!
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
For 32 years, Backroads has been perfecting the art of active travel. We are the tour experts. To see all our biking tours click here. For our selection of award-winning walking and hiking tours click here. For our selection of award-winning multisport tours click here.
Tuscany Biking
Casual Inns
Osteria dell'Orcia
Castiglione d'Orcia (2 nights) A beautifully restored 17th-century post station set in the Tuscan countryside.
Villa Curina Resort
Castelnuovo Berardenga (1 night) A tranquil 16th-century villa with wooded grounds, an Italian-style garden and a small church with frescoes by Arcangelo Salimbeni. (pool, tennis, solarium)
Belvedere di San Leonino
San Leonino (2 nights) Surrounded by vineyards and cypress trees, this hotel offers panoramic views of Siena.
Tuscany Biking
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
- 21 miles
- 1200 feet elevation gain
Day 2
- Levels 1 to 5 4 Route Options Available
- 20, 35, 48, 60 miles
- 1400 - 4710 feet elevation gain
Day 3
- Levels 2 to 5 3 Route Options Available
- 30, 53, 74 miles
- 2810 - 4910 feet elevation gain
Day 4
- Levels 2 to 3 3 Route Options Available
- 26, 38, 40 miles
- 2690 - 3750 feet elevation gain
Day 5
- Levels 2 to 5 3 Route Options Available
- 29, 46, 59 miles
- 1930 - 5050 feet elevation gain
Day 6
- Level 1 1 Route Option Available
- 12 miles
- 780 feet elevation gain