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Self-Guided Bicycle Tours in Italy: Bicycle Cortona, Montepulciano and Montalcino in Southern Tuscany

The Facts | Full Itinerary | Interactive Map

This self-guided tour of Tuscany covers a small but stunning part of Tuscany near the border with Umbria. Discover the beauty of Montepulciano, Cortona, Pienza, the Val d'Orcia, Montalcino and its famous Brunello wine, and Siena. This is a relaxed tour with two three-night stays so you are not always packing. If you wish to take a day off, two of your hotels have pools (available in season). The tour ends in Siena where you may wish to spend an extra day or two. Of course, food and wine also play an important role on this tour; you'll taste homemade pasta, local cheese, and typical soups of Tuscany, so Buon Appetito!
Highlights Montepulciano, Montalcino, Siena and its beautiful town center, Rolling hills of Tuscany
Includes 7 nights in 3 or 4 star hotels; 7 breakfasts; 6 dinners (drinks excluded); use of a quality 24-27 speed racing or hybrid bicycle); detailed route descriptions; map; optional rides daily; suggestions for last dinner and lunches; luggage transfers
Countries Italy
Begin/End Chiusi-Chianciano/Siena
Arrive/Depart Rome Fiumicino (FCO), Florence Airport (FLR) or Bologna Guglielmo Marconi Airport (BLQ)
Total Distance 366 - 500 km (227 - 311 miles); 3 night stays allow for rest days for those who wish
Daily Distance 0 - 80 km (0 - 50 miles); additional mileage is always available
What to Expect Hill and ridge rides in one of the world's most stunning landscapes. Easy loop rides for those who prefer to spend time by the pool (depending on the season)
Rating 301
The beauty of multiple-night stays is you can take long or short rides at your pleasure. Each day involves some hills but you decide how far and how many.
Notes Any variation to the tour including hotel upgrades and itinerary modifications will incur a 150 Euro fee
Terms Terms & Conditions


Click to view a map for this tour.
Click here to view a map of this tour.

Dates & Prices

Dates Price Single Supplement*Next Step
Tour departs every day. €1445300 Euros (singles traveling with others pay a 250 euro supplement)Request space on this tour now!