Tuscany Bike Tour

Seven nights; six 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. Pickup available at Poggibonsi train terminal, 16:00. Please contact us to arrange alternate plans.

Finish: Chiusi train terminal near Montepulciano, 10:00, day eight.

Day 1


Pick-up at the Siena train station at 15:00, or contact us for pickup at Poggibonsi train station at 16:00, for a transfer to your idyllic hideaway in the Rennaissance gem of San Gimignano – town of medieval towers, high in the Chianti hills. D (Meal inclusions provided for guided trips. Self-guided trips include breakfast only)
Hotel La Cisterna, or

Hotel L’Antico Pozzo; San Gimignano

Day 2

Ride one of three loop options ~30km, 52km, or 62km

This is a wonderful introduction to the Tuscan countryside, with opportunities for wine tasting, idyllic picnics, and such an abundance of intriguing smells that your head will reel with delight. BL
Same lodging

Day 3


An exhilarating ride through forest and field on some of the least traveled roads in the region. You will ride through quiet villages, each with its share of history, character and charm, unique to this corner of the world. Linari and Piazza are two of the smaller villages often missed - you may visit both on your way to Radda in Chianti. BLD
Relais Fattoria Vignale, Radda in Chianti

Day 4


A loop ride in the delightful hills of Chianti, with choices about whether you go to the highest point in Chianti at Monte Luco, or a more leisurely pedal through vineyards and olive groves, followed by a visit to Castelli di Brolio, one of the most respected wine producers of the area. Wine tasting, lunch, and a short ride back to your inn await you. BL
Same lodging

Day 5


A challenging ride along the ridge road to Asciano, then through gentle cypress-lined lanes to the southern Tuscan hills finishing just outside Montepulciano and Pienza. In this area, you’ll have chances to try the famous Vino Nobile di Montepulciano, famous as far back as the year 790! The '97 and '98 vintages are said to be the best in over 50 years! You will stop for lunch near the Abbaie di Monte Oliveto Maggiore, where you can visit renaissance frescoes, the cloisters, and bask in the mid-day peacefulness. BLD
Locanda La Costa, or

Hotel La Chiusa; Montefollonico

Day 6


A loop ride through some of the finest hill towns of Southern Tuscany. You’ll visit Montefollonico, Monticchiello, Castellúccio, and a village where much of the English Patient was filmed. While in Montepulciano you’ll have the opportunity to visit the little 18th century church of San Bernardo, Palazo Bucelli, with its Etruscan and Latin inscriptions in the lower walls and, the famous Montepulciano Piazza Grande which is surrounded by 14th and 15th century buildings. You’ll also have the opportunity to explore Pienza, which served as the set of Zefferelli's Romeo and Juliet. This ideal town was a dream of Pope Pius II, who died before its completion. However, despite the passage of time the harmony he felt has not been disturbed. BL
Relais Il Chiostro di Pienza, Pienza; or

Podere Dionora, Montepulciano

Day 7


You’ll follow a delightfully quiet route as you make your way to the Roman Baths of Bagno Vignoni, where the Town Square is a thermal spring. You’ll then cross the hilly Val d’Orcia, stopping to reflect upon life at the abbey in San Ántimo, where you may hear the monks sing Gregorian chants. You can stop for a walk and lunch in Montalcino, buy some wine and honey at the castle, then ride downhill toward San Quirico d’Orcia and back to your hotel to prepare for our final feast together. BD
Same lodging

Day 8


Following your breakfast, there is a morning transfer to Chiusi-Chianciano train terminal (a stop on all major Florence-Rome lines). B


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. Beginning near Florence with a pickup at Poggibonsi or Siena, you will spend the first two nights in spectacular San Gimignano, famous for its abundance of stone towers. You will then cross the Chiantigiana route through the premier wine region of Chianti. On your way toward the hills of Southern Tuscany, you will have ample opportunity to sample wine, honey and olive oil, as well as being fuelled by the gastronomic indulgence of some of the region’s finest chefs. You will repose in small inns known for their character and charm, and will fall, if you have not already done so, in love with the area which D.H. Lawrence referred to as "the perfect center of man's universe". After visiting Montepulciano and Montalcino, tasting what are perhaps Italy's most complex wines - the Vino Nobile and Brunello di Montalcino, and stopping to listen to the Gregorian monks chanting in an awe-inspiring cathedral, you will enjoy the evening ambience of your peaceful hotel in Pienza. 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.

Maps & Elevations

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 3575 C 3995

(per person, includes 8 days, 7 nights, 7 breakfasts, 5 light picnic lunches, 4 dinners, guide and van support, maps and route notes, luggage handling, taxes)

US 3095 C 3495

(per person, includes 8 days, 7 nights, 7 breakfasts, maps and route notes, luggage transfers, 2 required transfers, taxes)

Single Occupancy

US 895 C 995

Bicycle Rental

Hybrid: US 175 C 195
Full Carbon Racing: US 355 C 395

All details and pricing are subject to change without notice.