Tuscany Bike Tour

Six nights; seven days of classic bicycle touring in the hills of Chianti and Southern Tuscany.
“Scenery was fantastic, everywhere I looked it was another postcard shot!” – Kay P.


Start: Siena train terminal 15:00, day one. Please contact us to arrange alternate plans.

Finish: Siena train terminal 14:00, day seven.

Day 1


Meet at Siena late in the afternoon to experience what many believe to be Italy’s loveliest medieval city. Stroll along red brick lanes, visit the cathedral and art and history museums, and linger in the centuries-old Piazza del Campo before unwinding in your inn’s garden terrace. D (Meal inclusions provided for guided trips. Self-guided trips include breakfast only)
Albergo Chiusarelli, Siena

Day 2

Monteriggioni Loop 46km or 61.3km

Enjoy a loop ride through the countryside surrounding Siena, including a visit to the fortified town of Monteriggioni. The ride today is predominantly paved but there are some gravel sections, and one significant climb of approximately 300 meters over 4 ½ km; a pleasant warm up ride for the days to come. Return to Siena with time for independent evening explorations. BL
Same lodging

Day 3

Siena to Sant’Angelo in Colle 54.6km

Begin with some easy cycling, following paved and gravel roads from Siena through the Crete Senesi. The final 20km of the ride includes a steady climb as you skirt the cities of Buonconvento and Montalcino on your way to the village of Sant’Angelo in Colle. Today’s route takes you into the heart of Tuscany’s most well-known wine growing regions. You will cycle past vast vineyards of Sangiovese, which in Latin means, “the blood of Jupiter”; these grapes have been used in the Brunello di Montalcino since the 14th century. BLD
Castel Brunello, Sant’Angelo in Colle

Day 4

Montalcino Loop 38km

A short loop ride through vineyards and countryside of the Val d’Orcia to Montalcino allows for an early stop at the Romanesque Abbey of Sant’Antimo. Set among ancient olive groves and fields of wheat, the resident Gregorian monks gather seven times a day to chant their prayers; they also produce a unique selection of artisanal tonics and tinctures available at their pharmacy. Continue to the medieval hilltop gem of Montalcino, a good spot to explore before lunch. The return ride to Sant’Angelo in Colle travels through oak forests and along ridge roads with vast views of the surrounding vineyards and fields. B
Same lodging

Day 5

Sant’Angello in Colle to Rapolano Terme 54.4km

Ride north through the Senesi, passing Montalcino on your way to Rapolano Terme where the healing thermal baths of San Giovanni and terme Antica await. Along the way, visit large renaissance fresco paintings at the Abbazia di Monte Oliveto Maggiore, a large Benedictine monastery that was founded in 1320. Continue cycling through the ancient village of Asciano to Rapolano Terme, stopping in Serre to see the Old Grange and Olive Oil Museum. The thermal waters flowing from the springs at Rapolano have been easing sore muscles and stressed minds since Roman times. BLD
Castello delle Serre, or upgrade

Terme San Giovanni, Rapolano Terme

Day 6

Rapolano to Radda in Chianti 52.3km

Today you will ride through the gentle hills and valleys of Il Chianti. This region is renowned for its olive groves and vineyards which produce some of Italy’s finest oils and wines, including the esteemed Classico easily identified by the iconic black rooster brand. Your route will take you past the historic Castello di Brolio, a huge medieval estate and home of the oldest winery in Italy. BLD
Relais Vignale, Radda in Chianti

Day 7

Radda in Chianti to Siena 42km

Your final ride follows a mix of gravel and paved roads back to Siena where your tour concludes in the early afternoon. On the way, you’ll visit the monument at Montaperti, which signifies the site of Italy’s bloodiest medieval battle. It is now a peacefully, quiet place and provides an ideal backdrop to contemplate the past weeks escapades. You may choose to spend more time in Siena or proceed to Florence or other nearby destinations. BL


Note about the route:

Most of the route is well paved, but there are a couple of short gravel stretches. There are lots of hills. This trip is best suited to experienced cyclists, and although relaxed riders are welcome to guided trips, they will require van support on longer climbs and distances.

Tuscany straddles the Apennine hills in the heart of Italy, where cypress trees, olive groves, vineyards, and soft, verdant hills create a landscape reminiscent of Renaissance paintings. Giotto, Michelangelo, and Leonardo da Vinci traveled these same landscapes centuries ago, and fortunately, not much has changed. Their influence is evident in many towns and villages along the route, and as you ride quiet routes along sun-drenched ridges, you will enjoy expansive views over the landscape of their inspiration. If you can spare some extra time, we recommend that you plan to spend a day or more in Siena or Florence before or after your Freewheeling Adventure, to see the riches these ancient cities have on display.

Map & Elevations

Click here for the elevation profile
Day # Daily distance
  Siena exploration
46km or 61.3km

Learn more

Spend a week before or after you tour exploring other parts of Italy and Western Europe.

Join one of our Eastern European tours.

Spend some extra time in Venice or Rome.


US 3765 C 4295 (per person, double occupancy)

Includes 7 days, 6 nights, 6 breakfasts, 5 lunches, 4 dinners, guide and van support, maps and route instructions, luggage handling, taxes

US 2885 C 3295 (per person, double occupancy)

Includes 7 days, 6 nights, 6 breakfasts, maps, route instructins, inn to inn luggage transfers, essential transfers, taxes

Single room

US 955 C 1095


Hybrid: US 225 C 265
Gravel: US 330 C 395
Electric Assist: US 330 C 395

All details and pricing are subject to change without notice.