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Tuscany is an iconic name, symbolizing the good life - a vacation to enjoy all that is good: food, sun, lifestyle, wine, amusement, and relaxation. The culture of the region adds charm, and you can indulge yourself in this opulent way because you will cycle the famous undulating countryside. This Tuscany cycling tour starts in Pienza, and makes its way to Florence, where along the way you will visit the villages that have made Tuscany famous. You can enjoy very charming 3/4 star accommodations and devour your choice of divine mediterranean cuisine. The hilly terrain makes this tour somewhat challenging!
Enjoy deluxe 3/4 star lodging while discovering all the charms of Tuscany on a self guided bicycle tour.
Duration: 5 days & 4 nights. Note that we can accommodate custom requests for Tuscany and Umbria including villa stays.
Dates : March 15-November 15. This is self-guided touring and offers total freedom of dates - you can choose whatever dates you wish. We can accomodate small parties of 2 persons up to large groups. Custom guided groups are possible for groups of 6 or more; please inquire.
Level 3 - Consistently hilly countryside with mostly hilltop finishes; challenging terrain can be moderated or made more challenging by daily mileage. This is a self guided tour - see what all that includes!
Options
Ride options - longer/shorter
Florence/Rome addons
Custom tours for groups
Villa stays - with custom riding; for groups, (1 week minimums)
Marco and Giuliana are our local experts; they live in Tuscany and will meet you for orientation on arrival day as well as provide emergency support throughout your trip.
"I wanted to write and let you know how marvelous out trip to Tuscany was and thank you for arranging such a wonderful biking tour. Giuliana and Marco were terrific and made sure we had everything we needed. The route maps were easy to follow, our hotels were terrific and the bikes satisfactory for our Tuscany adventure!! "
- Julie S./USA
Click on a day to see that days itinerary.
DAY 1 DAY 2 DAY 3 DAY 4 DAY 5
Day 1 | Arrival Day
We'll meet you at Pienza, the purest Renaissance town in the world (you will arrive by the train to Chiusi-Chianciano station, a major stop on all the Rome-Florence lines). Your charming hotel overlooks the val d'orcia. Pienza is a rare masterpiece: entirely rebuilt between 1459 and 1462, it was the brainstorm of Pope Pius II and today is memorable not only for its architectural purity but also for its exquisite food shops. As you stroll through the pristine streets, you might decide to stock up on truffle-flavoured cheese, wild herbs or other delicacies to take home or to use for an informal dinner with a bottle of Chianti wine. Or maybe you'd rather reward yourself with some ice cream at our favorite gelateria. Dinner on your own. Some foods to try in Italy.
Corso Rossellino, 26
Relais Chiostro di Pienza is situated in the heart of Pienza, a Renaissance city planned by Rosselli...
Day 2 | Ride Day
Your tour starts with a circular ride from Pienza. Be sure to stop along the way to visit the remote convent where parts of The English Patient were filmed, and in the enchanting little hamlet of Castelmuzio. By lunchtime you'll come to Montepulciano, the jewel of southern Tuscany. After relaxing a while, return to Pienza with a stop in the village of Monticchiello, the quintessential Tuscan hill town. Overnight at the same hotel; dinner on your own again. Level: Moderate to easy Distance: 50 km. (Breakfast included)
Corso Rossellino, 26
Relais Chiostro di Pienza is situated in the heart of Pienza, a Renaissance city planned by Rosselli...
Day 3 | Ride Day
Ride from Pienza to Montalcino, with a pause in fairy-tale Bagno Vignoni, a miniature spa that is among the most unique towns in Europe. You can have lunch in Castiglione d'Orcia, then push on to the monastery of Sant'Antimo, where you might catch one of several vesper services performed each day by the monks. The famed wine town of Montalcino is your destination. Visit the fortress to see a breathtaking view of the entire valley you've just biked, then reward yourself with dinner at our favourite wine cellar. Accommodations are at a panoramic three-star hotel. Dinner on your own. Level: Moderate to strenuous. Distance: 46 km. (B)
Montalcino
A charming retreat in the heart of Montalcino, a family-run Hotel in a warm and quiet building, faci...
Day 4 | Ride Day
Ride from Montalcino to Siena. On the way you'll coast along the forested crest of a ridge, home to the famed Monte Oliveto Maggiore monastery. Stop here to visit the beautiful buildings and perhaps have lunch at the restaurant. Afterwards, you'll travel through the fascinating area called Le Crete, Tuscany's answer to the Badlands. Late afternoon arrival in Siena. You will stay in a historic four-star hotel right in the center of town. Dinner on your own. Level: Moderate to strenuous Distance: 60 km. (B)
Siena, Toscana, Italia
Il Chiostro del Carmine is a restored 14th-century monastery, with great views of the countryside. I...
Day 5 | Departure Day
Departure after breakfast, at your leisure. If you want to go on to Florence, we can arrange transportation and hotels. Trains, car rentals can be arranged as well additional stays throughout Italy. (B)
Deluxe lodging 3 and 4 stars - double room with private bath, buffet breakfast daily, all luggage transfers from hotel to hotel, local emergency support throughout your tour during daylight riding hours, arrival orientation and bike set up, route maps, route cue sheets with suggestions for visitation and site information, all pre and post travel planning services and a package of pre-travel documents sent electronically to help you prepare for your trip. Bike rental is not included but available for a small supplement; we highly recommend our rentals; see the bike tab for details.
There is an upgrade option available for this tour as well with upgraded hotels or upgraded rooms; please see the price section. All hotels in either the 3 and 4 star version or upgraded 4 star are superior hotels with excellent locations and amenities. See the information shown for each day in the Itinerary tab.
Lodging on this tour is the same as that found in guided group tours costing $3000 and more!
Cycling in Tuscany is one of the best ways to experience this famously romantic countryside. Traveling from one famous village to another along small country roads, this bicycle tour can be adapted to your needs.
Accommodation: [Virtual Hotel Tour] 4 nights in deluxe hotels: Pienza - Piccolo hotel La valle or Il Chiostro, Montalcino- Il Giglio or Hotel dei capitani, Siena-Hotel Chiostro del Carmine. These properties are all excellent hotels offering views, and charming typical Tuscan ambiance. They are also in demand, so last minute requests can be difficult. In case of no availability; we will check equivalent alternative hotels that may require a change in price.
See the list of hotels in the Itinerary tab for the most up to date hotel information.Options
Ride options - longer/shorter
Florence/Rome addons
Custom tours for groups
Hybrid Bike Rentals are available for a supplement of 95 euros, please see the Bike Rental tab for all details about the bikes we offer. Road bikes are also available for 140 euros.
Private transfer Chiusi to Montepulciano or Pienza: 67 euros up to 4 persons.

Bike rentals are available for every tour. We offer top quality custom built hybrid and road bikes.
Note: pedals are flat or with clips; if you bring your own clipless pedals and shoes we can install them.
Bike: [Click for image and more details ] Custom hybrid; aluminum frame with carbon fork, Shimano Ultegra or Deore; 3x9. Bikes come equipped with handlebar bag, lock, water bottle, gel saddle, tire repair kit, cycle computer. Hybrids are fitted with thin tires for better road performance. Rental rate is 95 euros for the tour.
Racing models also available see details . Rental rate is 140 euros for the tour.
Hilly terrain, rated as intermediate to advanced. All towns where lodging is located are perched hilltop villages.
A Cannondale tandem is also available for experienced tandem riders. Persons from 5 ft to 6-5 can be accommodated. Bike quality is top; averaging $1500 each retail.