Bicycle touring Tuscany

Cycling in Tuscany


Bicycle Touring Tuscany

Cycling in Tuscany is a joy with great scenery, food, wine and the people you meet. You will be riding on quiet roads in the countryside flanked by wild flowers or vineyards and stately trees. Stay in a villa or quaint hotel in walled medieval villages with pedestrian friendly streets. No, it is not a dream and really exists, read about my bicycle touring experiences of Tuscany and which will help you plan your own tour whatever your level of experience.

With any bicycle touring pack lightweight with the proper cycling clothing for a more comfortable ride. This page is based on a self guided bicycle tour of Tuscany, although many of the guided tours include many of the same routes. We started in the south at Chiusi and rode north to Lucca and Pisa as these towns offer direct train service to Rome.

Starting in Chiusi and heading to Montalcino

Tuscany Cycling
Cycling near Chiusi

We started our bicycle touring of Southern Tuscany in the town of Chiusi as there was direct railway service from Rome and we have brought on own bicycles.

And although the train station was in a valley the town itself and our hotel was up a hill, perhaps a glimpse of things to come. Chiusi provides car free streets to explore and excellent views of the surrounding countryside. We headed to a local store to pick up lunch for the next day of riding. Apparently, it is the custom to just point to the item you want and the shop keeper will get it for you and place it in a bag. Not sure what was said to use in Italian but we got the message that you just don’t pick up an item like you would in North America.

The next morning we headed south a short distance in the direction of Cortona, before turning to the west. A popular route is to continue to Cortona but we had elected to head towards Siena. Along the paved roads there was little traffic and the scenery was just what you would expect – tall narrow trees, hilltop houses, olive trees and we cycled over the rolling hills.


Before long we arrived in Montepulciano, well known for its wines and stopped to explore the long winding streets and have lunch. Then it was down a hill (okay we stopped for pictures) and we continued the ride to Pienza. Along the way many people were stopping to also take a picture in the fields of poppies so we did too.

In Pienza, again we stopped and joined other visitors as they explored the church and narrow streets. We also met members of an Italian bike club out for a day ride who were kind enough to give us a gift of club jerseys. People everywhere were respectful of cyclists and we saw a lot of cyclists, mostly from local bike clubs. Just past Pienza along on one of the many hills we stopped for pictures, standing in a field of red poppies which bloomed everywhere during May.

San Quirico d’Orcia is very quiet but worth a brief stop before moving on. We arrived at a never ending hill (or it seemed that way) as we climbed up to Montalcino. We now know that any town with “Mont” in the name means a climb, at least it was gradual.

Montalcino, Italy

We spent two nights in the walled town of Montalcino, with one morning spent exploring Spalti Fortezza Montalcino (castle) and another the shops along pedestrian friendly streets. There seemed to be some sort of festival taking place as the streets were draped with flags and balloons. Meanwhile one member of our group wishing for some extra riding took a day trip south to the medieval hill town of Sassofortino.

Riding from Montalcino to Siena

Leaving Montalcino was harder than expected. Although a long, long descent we were riding on loaded bicycles and were not quite used to riding with the added weight, but it did get easier throughout the trip. The temperatures in May were 30 to 35 C (86 – 95 F) in the shade so stops for frequent water breaks were the normal.

Although there are no signed bicycle routes the local road signs made finding our way easy as we cycled the hills of the Tuscan countryside. We stopped in the little historic town of Murlo for a brief visit and discovered that in Tuscany everything closes from 1 p.m to 4 p.m. We did however find find a restaurant open for lunch near Grotti. Normally we would have just enjoyed a picnic lunch but it was so hot we needed to get indoors for a brief break and as we were the only customers we got excellent service.


Continuing we encountered the only busy roads of the entire trip with a lot of traffic as we got into Siena. We spent a few nights in this walled city which is not as touristy as Florence. Each morning just head to the Piazza del Campo in the city center to watch the people, the fountains, have a leisurely lunch at one of the many cafes or climb the tower at the town hall for views. Do wall the city streets (no cars) and do visit the grand Duomo (catherdral). There was a weekly market covering several streets well worth visiting. Markets are common in Tuscany, moving from town to town each day, but this was one of the largest we encountered. Siena is most famous for its medieval horse races, called Il Palio, around the city square during the summer.

On to San Gimignano

Bicycle touring clothing
Bicycle touring in Tuscany

There was no traffic as we headed north out of Siena, most likely as all the cars were on the nearby expressway. None of the travel guides mentioned this route but it turned out to be quite nice. As we were cycling along we noticed the hilltop town of Monteriggioni built in 1203, a slight detour to the right and well worth the stop. A number of tourists were exploring the shops in this quaint walled town and one provided us restaurants tips for our next stop.

San Gimignano
San Gimignano

Continuing our ride we encountered the only rain of the trip, so we stopped for about an hour in a cafe in the town of Colle di Val d’Elsa. We could see San Gimignano in the distance on a hill with its many towers. It was a long climb up, although the hill is gradual, and the first person up was standing next to a gelato store just outside the town walls when I arrived.

I can’t say enough good things about San Gimignano, which was to be our home for four nights and we settled in at an historic hotel right on the main square. No cars are permitted in the town center and during the day tourists invaded the many shops that crowded the streets. In the evening we seemed to have the town to ourselves. During the day do visit the weekly market, the churches, various shops and museums. This towns has some amazing restaurants tucked away along the pedestrian only alleys.

Today there are 13 towers that dominate the skyline of the walled hilltop town. They were built by nobles in the 12th and 13th centuries as this was on a major pilgrim route of the time. One of the towers is still open for visiting and you can also walk along a short section of the town walls on the western side.

Certaldo, Tuscany
Day ride to Certaldo

However, we also had other plans using San Gimignano as a base for taking a hilly day ride to the Roman city of Volterra to view the forum and other historic ruins. On another day we cycled to the town of Certaldo stopping for lunch on a patio restaurant, for a pizza of course. The pizza here is thin crust and wonderful as was the wine.

From San Gimignano to Greve in Chianti

Departing San Gimignano it was down downhill forever (or so it seemed) before crossing the bridge over the main expressway and starting a long, long climb to Castellina in Chianti. At least is was shaded most of the way. This town is famous for its wines so we had to stop for lunch and explore.

About to leave Castellina in Chianti we encountered the Migilia 1000 which is a vintage car rally throughout Italy and the roads were closed. However, much to our surprise the police waved our group of four cyclists through and we cycled the roads with spectators cheering us on as we rode this very hilly section of about 20 km. Fortunately for us the vintage cars seemed to travel in groups of about 25 cars so whenever a group came by we would stop and watch them before proceeding. We took a break in Panzano before proceeding to our accommodation in Greve.

Greve, Tuscany

We had decided to stay in Greve as it is located half way between Florence and Siena. You can rent a villa or apartment for the week and out choice was the Fattoria Viticcio, actually more of a apartment than a villa.

Fattoria Viticcio is a working winery, surrounded by vineyards a short bike ride and 20 minute walk from Greve which offers a Coop supermarket and weekly market around the main square. Our apartment featured several bedrooms, a full kitchen, patio with views of the vineyards, a swimming pool and daily visits from the owners 2 dogs and cat who seemed to approve of our small party.

Fattoria Viticcio,, Greve, Tuscany
Fattoria-Viticcio, our accommodation in Greve

Another advantage is that the owner does not sell directly to the public but does offer guests the opportunity to purchase great wine. As this family owned winery only features a few apartments it was very quiet as we sat on the patio sipping our excellent wine and taking in the view. Breakfast for the week was always at the apartment while dinners were split between restaurants in town and cooking for ourselves.

Chianti Cycling

Our first day ride took us to Panzano and through a scenic shaded valley and up a hill (of course) to Radda in Chianti, a walled town you just must explore. We really had no troubles finding roads to explore in the surrounding hills. On one day we even took a walk to the neighboring historic village of Montefioralle.

Ponte Vecchio, Florence
Ponte Vecchio, Florence

To reach Florence we took inexpensive local buses to avoid the heavy traffic on all roads around this very popular, but touristy city. When you arrive immediately walk over to The Accademia, as the line to see the Statue of David isn’t so bad first thing in the morning. Of course you will also want to visit the Uffizi Gallery, Duomo and Ponte Vecchio for a picture of the famous bridge across the river. That is not the place to buy souvenirs as things can get a little expensive by the bridge and remember whatever you purchase you will have to carry on your bicycle.

Cycling in Northern Tuscany

We left Greve for the long cycle of over 100 km to Lucca. The first part was very hilly, while the middle section around Empoli got very flat and was a little boring. However things picked up as we approached Lucca, the fields were lush, there were many canals and streams and it was quite scenic.

Lucca, Tuscany

Lucca, founded in 180 BC, should be on the must see list of everyone bicycle touring in Tuscany. The city walls are wide enough that you can even cycle for about 4 km around the top of this historic city looking in at the many churches and historic building. In fact this is so popular there are several bicycle rental outlets at the base of the walls. In the evening go for a walk along the tree lined walls are they are well lit and is popular with local residents as well.

Cycling in Lucca, Italy
Cycling atop walls of Lucca, Italy

Inside Lucca visit the unique Ginigui Palace which has a tree growing at the top of its tall tower, the Plaza Anfiteatro for some great gelato, Cathedral of San Martino, Church of San Michele In Foro and other interesting museums and palaces. A famous character known for his long wooden nose, Pinocchio, was first created in a nearby town so expect to see many souvenirs.

Leaning Tower of Pisa
Leaning Tower of Pisa

You can also cycle over to famous Pisa to see the tower and duomo (cathedral). The road route does feature 950 meter tunnel although you have a nice descent once you are through it. There is also a bicycle path part of the distance from Lucca to Pisa. We headed then headed for the train station heading back to Rome.


The months of May, June, September and October are best as it is not as hot and there are not as many tourists. Be sure to pack your short sleeve cycling jersey and shorts. Cycling in Tuscany is over hilly terrain but you are rewarded with great scenery, fine food and bicycle friendly local citizens.

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