Tuscany Biking
- A quintessential Tuscan experience from south to north
- Sample fine wines before dining on local specialties
- Relax at day’s end in cozy historic hotels, all with swimming pools
- Explore some of the region’s most celebrated towns, including Pienza, Montalcino, Siena and Radda in Chianti
- Pedal rolling hills past Brunello, Chianti Classico and Sangiovese vineyards
A Taste of Tuscany from Pienza to Siena & Chianti
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.
Days 1-2 Explore some of the region's most celebrated towns, including Pienza, famous for pecorino cheese, exquisite ceramics and Renaissance architecture 
After savoring Tuscan treats overlooking the Val d'Orcia, pedal cypress-lined roads through southern Tuscany's open undulating terrain Montepulciano, with its winding streets and hidden squares, invites a stroll Visit Abbazia di Sant'Antimo, a stunning Romanesque church overlooking grape vines and forests.
Day 3 Bike past exposed chalk hills of the Crete Senesi, often depicted in 14th- and 15th-century Florentine and Sienese paintings Climb through a sea of vineyards to the wine village of Montalcino, where enoteche pour samples and remarkable views reach as far as Siena on a clear day Check out Abbazia di Monte Oliveto Maggiore, the region’s most notable monastery.
Day 4 Engaging Q&A session with Dario Castagno, author of Too Much Tuscan Sun Sun-baked pastures dotted with sheep and crumbling stone farmhouses make way for oak woodland and olive groves Explore Siena on your own.
Days 5-6 Pedal rolling hills alongside Chianti Classico and Sangiovese vineyards
Get to know ridgetop Radda, the center of Chianti wine production, and Castellina, a medieval village with a unique arcaded passageway Looking for a gift? Family-owned Ceramiche Rampini offers ceramics hand-painted in the Renaissance tradition.
Guests Reviews About This Trip
I came in to this trip with very high expectations. Usually when that happens, you can only be disappointed. I was not disappointed. Everything, and I do mean everything, was absolutely fantastic. I was enthralled. Everything about this trip was so far above my expectations that I was stunned...the rooms, the biking, the leaders, all of it, just amazing. It was the best trip that I've had in 22 years.- Pleasanton, CA
I can see how these trips can become addicting. This was the BEST way to experience Tuscany. You are encouraged to be in the moment, focusing only on the road in front of you, the beauty that surrounds you and the food you will indulge in when you reach your destination.- Westport, CT
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
Casual Inns
Albergo le Terme
Bagno Vignoni (2 nights) This charming family-owned hotel overlooks the town's central piazza, whose ancient pool is fed by underground thermal springs. (pool, spa)
Borgo Casabianca
Asciano (1 night) A warm welcome awaits at this agricultural estate standing on a high ridge between the Chiana Valley and the famed Crete Senesi. (pool, tennis)
Villa Curina Resort
Curina (2 nights) A tranquil 16th-century villa with wooded grounds, an Italian-style garden and a small church with frescoes by Arcangelo Salimbeni. (pool, tennis)
Puglia Biking
Italy's Sun-Drenched Adriatic Coast
Classic:
Singles+Solos:
This Trip Is Rated Level 2-5
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 | Road Bike Average | Mountain Bike Average* | Walk & Hike Average |
|---|---|---|---|---|
| Level 1 | 2-3 hours | 10-20 miles | 10-15 miles | 2-5 miles |
| Level 2 | 2-4 hours | 21-30 miles | 16-20 miles | 5-7 miles |
| Level 3 | 3-5 hours | 31-40 miles | 21-25 miles | 7-9 miles |
| Level 4 | 4-6 hours | 41-55 miles | 26-30 miles | 9-11 miles |
| Level 5 | 5-7+ hours | 56-75+ miles | 31+ miles | 11-13+ miles |
*Mountain bikes are used in locations where the best riding is on a combination of dirt and paved roads. View trip locations
Daily Mileage Options & Cumulative Elevation Gain
Day 1
- Level 2 1 Route Option Available
- 23 miles
- 1800 feet elevation gain
Day 2
- Levels 2 to 4 3 Route Options Available
- 25, 35, 45 miles
- 1570 - 2570 feet elevation gain
Day 3
- Levels 2 to 5 3 Route Options Available
- 22, 42, 57 miles
- 1550 - 4070 feet elevation gain
Day 4
- Levels 3 to 4 2 Route Options Available
- 33, 50 miles
- 1270 - 2310 feet elevation gain
Day 5
- Levels 2 to 5 3 Route Options Available
- 23, 53, 64 miles
- 1880 - 4750 feet elevation gain
Day 6
- Level 1 1 Route Option Available
- 13 miles
- 670 feet elevation gain
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For 33 years, Backroads has been perfecting the art of active travel. We are the Tuscany tour experts. See our award-winning Europe Italy biking tours, Europe Italy walking and hiking tours and Europe Italy multisport tours.
