Are you interested in cycling in Tuscany?
Cycling in Tuscany is a joy with great scenery, food, wine, and the people you meet. Bike tours in Tuscany will have you riding on quiet roads in the countryside flanked by wildflowers, vineyards, olive groves, and stately trees. Stay in a villa or quaint hotel in a walled medieval village with pedestrian-friendly streets.
I have been cycling in Italy for years, including Tuscany, and it is always a special ride. Use my helpful guide to learn more about this journey.
The quiet roads I was cycling were lined by cypress and olive groves, vineyards too, and there were long winding hilly climbs that led to wonderful stone villages. Italian drivers all seem to think this is a Formula One race route and drive fast, yet are generally gentle around cyclists, as there are many riders on the roads, so I never felt this was an issue.
As there are no signed bicycle routes in Tuscany, you definitely need a guide like this to navigate the backroads. One thing I liked was that although there were no bike route signs, frequent road signs were pointing to the next town, so navigation was not an issue.
No, it was not a dream and really exists. Read about my great experiences bicycle touring in Italy, including Tuscany, which will help you plan your tour, whatever your level of experience. There are several districts where you can take bike tours in Tuscany, which may be combined to form journeys of long distances.
Bike Touring in Southern Tuscany
Cycling from Chiusi
Our small group started our cycle touring in southern Tuscany on our first day in the town of Chiusi, a hilltop village with sweeping views of the area. It is located on the direct main train route from Rome’s Fiumicino Airport (with ample time for a connection at Termini Station) for easy access, and we had no problems putting our bicycles on the train.
Although the train station was in a valley, the town itself and our hotel were 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 shopkeeper will get it for you and place it in a bag. Not sure what was said to us in Italian, but we got the message that you just don’t pick up an item like you would in North America.
You can take your Tuscany bicycle tour northward to Cortona, made famous in many movies and television shows, and a great overnight location; however, we felt there was a better way and headed in a different direction to the west.
Along the paved roads, there was little traffic, and the scenery was just what you would expect with tall, narrow trees, hilltop houses, and olive trees as we cycled over the rolling hills. I expect you will fall in love with the scenic landscape covered with red poppies in the spring or sunflowers in the autumn, much as I did.
Montepulciano, Pienza & San Quirico d’Orcia
Our cycle vacation continued riding over a few rolling hills to Montepulciano, our first stop and home to great wines and many historic buildings, long winding streets, and our lunch stop. One thing you can do is enjoy an exclusive wine tasting combined with a typical Tuscan lunch in an ancient wine cellar in the heart of Montepulciano.
Then it was down a hill (okay, we stopped for pictures), and we continued the ride to Pienza.
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, many drivers had stopped for pictures, so we did as well, standing in a field of red poppies that bloomed everywhere during May. Later in the year, you might see sunflower fields.
Some easy cycling over the rolling countryside brought us later to San Quirico d’Orcia, very quiet but worth a short stop to investigate. 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
Your bicycle tour then brings you to Montalcino, after a long 6 km climb to the top of a hill. But once you arrive, stop here for a night or two to explore the amazing castle and many streets.
We spent two nights in the walled town of Montalcino, with one morning spent exploring Spalti Fortezza Montalcino (medieval 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.
Our hotel, the Bellaria, was just over a kilometer from town, so if I went in the future, I would stay closer to the center with restaurant options.
You can take a winery and tasting tour in the area. 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; 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 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 a restaurant open for lunch and some great food near the small village of 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.
Cycle Touring in Central Tuscany
Siena
This is the center of the Tuscan region. The main street of Siena within the city walls is a meandering and wonderful pedestrian walkway flanked by shops that open up into the City Hall and Piazza del Campo. The tower at City Hall is worth the half hour it takes to climb for outstanding views of the region, as is the adjoining plaza for some snacks and wine tasting.
Most Tuscany cycling tours visit this city, and we did as well. 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 and the fountains, and have a leisurely lunch at one of the many cafes.
Do walk the city streets (no cars) and also visit the grand Duomo (cathedral). There are a lot of churches in Europe with outstanding architecture, and this is one that you should visit. Get a ticket so you can observe the ornate decorations adorning the interior of the Duomo, and admire Pinturicchio’s frescoes in the Piccolomini Library.
You may wish to join a Siena walking tour during your time in the city.
The weekly market is absolutely huge, with everything from shoes to food for sale. covering several streets. Markets are common in Tuscany, moving from town to town each day, but this was one of the largest we encountered.
It can be difficult to locate accommodation in Siena, so check out your options with VRBO, with many apartments plus B&Bs in the city.
Siena is most famous for its medieval horse races, called Il Palio, around the city square during the summer months.
Cycling from Siena to San Gimignano
There was no traffic as we headed north out of Siena, most likely because 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.
Several tourists were exploring the shops in this quaint walled town, and one provided us with restaurant tips for our next stop.
Insider Tip: Your cycling vacation in Tuscany now takes you north to Monteriggioni, an impressive hilltop fortress where we stopped for lunch (recommended).
Then, 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.
San Gimignano
I can’t say enough good things about San Gimignano, which was to be our home for four nights, and we settled in at the 14th-century Hotel La Cisterna right on the main square with excellent views of the town and Le Terrazze restaurant with superb food.
San Gimignano is a medieval town that does not permit cars on its streets and receives plenty of daytime visitors, invading the shops. However, the evening is quiet as the day visitors have left, so we spent it seeing the stone buildings night-lit, as we seem to have the town to ourselves.
Today, 13 towers 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 pilgrimage 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 for panoramic views.
See the Town Hall, use your admission tickets to the Duomo to discover beautiful medieval art, and climb up the Torre Grossa for breathtaking views.
During the day do visit the weekly market in the main square, the churches, the town wall, and various shops and museums. This town has some amazing restaurants tucked away along the pedestrian-only alleys. You can also take a Tuscan Farmhouse cooking class while in San Gimignano.
Certaldo
From San Gimignano, you can make a hilly day trip to the Roman city of Volterra (worth the effort), the site of the Roman Forum, and other historic ruins. We did a short ride to Certaldo to enjoy pizza, which only the Italians can make on a terrace overlooking the valley, before riding back. The pizza here is thin crust and wonderful, as was the wine.
Cycling from San Gimignano to Greve in Chianti
Leaving San Gimignano, we soon encountered a long downhill forever (or so it seemed) before crossing a bridge over the expressway and then an equally impressive and long ascent to Castellina in Chianti, our lunch stop. This is where you can purchase the famous Chianti Classico wine as well, and many visitors do when on a wine tour.
About to leave Castellina in Chianti, we encountered the Miglia 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. Passing several Chianti vineyards, we took a break in Panzano before proceeding to our accommodation in Greve.
Greve
Next, we cycled through the vine-covered Tuscan hills to Greve, where we rented a villa, actually more of an apartment, at a working winery for a week. We decided to stay in Greve as it is located halfway between Florence and Siena.
During our one-week stay, we rotated between Greve restaurants and cooking in the apartment. We were also sure to visit the weekly market in the town square.
Fattoria Viticcio is a working winery, surrounded by vineyards, a short bike ride, and a 20-minute walk from Greve, which offers a Coop supermarket and weekly market around the main square.
Each of the 4 apartments features several bedrooms, a full kitchen, a patio with views of the vineyards, a swimming pool, and daily visits from the owners’ 2 dogs and a cat who seemed to approve of our small party.
Another advantage is that the owner does not sell directly to the public but does offer guests the opportunity to purchase great wine; you just need to call him when you need a bottle.
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. Life was good. Breakfast for the week was always at the apartment, while dinners were split between restaurants in town and cooking for ourselves.
VRBO also has plenty of apartments and cottages in the area.
Chianti Cycling
With no shortage of scenic routes, daily day trips throughout the Chianti Region were the order of the day, with our first to nearby Panzano and later 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 trouble finding scenic routes to explore in the surrounding hills. One day, we even took a walk to the neighboring historic village of Montefioralle with its stone houses crowding the alleys.
One member of our small group had mechanical issues with their road bike, so we were fortunate that there was a bike shop in town that was able to fix the issue.
Florence
Of course, most Tuscany bike tours include Florence, and you will want to visit the city as well. To reach Florence, we took inexpensive and frequent 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.
Consider the Skip the Line of Uffizi and Accademia Small Group Hidden Highlights Walking Tour to save time. Also popular is the Florence Sunset Walking Tour with Wine & Food Tasting (pasta).
This is a great day because, of course, you will also want to visit the Uffizi Gallery, Duomo, and Ponte Vecchio (bridge) 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, and you want to keep things lightweight.
Bicycle Touring in Northern Tuscany
An early morning departure from Greve (or Florence) for the final stage was a long 100 km on your cycle tour of Tuscany, which was easier than the arrival, as it was along quiet roads.
On our morning ride, we headed west, which started with some hills, 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
For the best experience, we spent a few nights in Lucca, the gem of the region, with walls so wide there is a bicycle route around the top creating a 44-kilometer loop (2.5 miles) around the city. Our comfortable room was near the city walls, which made exploring easy.
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 (2.5 miles) around the top of this historic city, looking in at the many churches and historic buildings.
This is so popular that there are several bicycle rental outlets at the base of the walls. In the evening, go for a walk along the tree-lined walls, which are well-lit and are popular with local residents as well.
Inside is a medieval city with shops, restaurants, and churches. We went to visit the unique Ginigui Palace, which has a tree growing at the top of its tall tower, the Plaza Anfiteatro for some great gelato, the Cathedral of San Martino, the 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.
Discover the secrets to turning out fresh pasta and classic tiramisù like a real Italian ‘mamma’ with a home cooking class.
Insider Tip: Although not as well known as its neighbor, Pisa, for cyclists, it is more interesting to stay in Lucca.
Pisa
Our ride finishes on a short 29 km (18 miles) cycle over to the famous Pisa on your Tuscany bike tour, if you have enough free time to see the tower and duomo (cathedral) inside the city walls.
The road route is lined with cypress trees, but it does feature a 950-meter tunnel (very scary), although you have a nice descent once you are through it. There is also a bicycle path for part of the distance from Lucca to Pisa. We then headed for the train station, heading back to Rome.
From Pisa, we took the train back to Rome along the Tuscan coast, but others may want to continue their bicycle tour north along the Mediterranean coast to the home of Pinocchio.
Where to stay in Tuscany & Resources
This is where we stayed during our bicycle tour in Tuscany, and you can use Expedia or booking.com to book your accommodation:
La Sfinge, Chiusi – not a lot of choices in this small town, but this worked out well
Hotel Bellaria, Montalcino – a little out of town but a nice small hotel with a pool, although on future trips I would likely stay in the town close to restaurants. May not be available, so try booking.com
B & B Villa Fiorita, Siena – a nice place located just outside the walls and an easy walk everywhere. Also easy to store our bicycles.
Hotel La Cisterna, San Gimignano – strongly recommended, right in the main square
Fattico Viticcio, Greve – working winery with apartments, can walk to town
Hotel Bernardino, Lucca – very basic accommodation, just outside the town walls, I would consider another option.
Other Resources
Travel Insurance – during your visit to Italy
Trip.com – for train connections to and from Tuscany
Tuscany Cycling Tours
Taste of Tuscany – 8-day tour from Exodus
Classic Tuscany – cycling from Florence to Pisa self-guided tour
Southern Tuscany – self-guided tour including Siena, Cortona, & Montalcino
FAQs: Bike Tours in Tuscany
When is the best time to cycle in Tuscany?
The months of May, June, September, and October are best as it is not as hot and there are not as many tourists.
Is Tuscany good for cycling?
Yes, with the historic towns, wine, good food, beautiful landscapes, and patient drivers, Tuscany is great for cycle tours. But much of the terrain is very hilly.
Is Tuscany very hilly?
Tuscany is very hilly with numerous gradual hills; 6 km is not uncommon. Many villages with a name starting with “Mont” were placed on hilltops in the Middle Ages for defense, but these are what you want to visit.
Are there any EuroVelo routes in Tuscany?
The EuroVelo 7 Sun Route and the EuroVelo 5 Via Romea (Fracigena) cycle routes go through the heart of Tuscany.
Looking for more information on cycling in Italy?
If you’re planning a trip to Italy and looking for more information, consider reading some of my other posts:
- Cycling in the Venice region includes Venice, Padua, and other historic cities
- Riding from Austria to Verona along the Adige Cycle Path
- Other rides in Italy can be found in the 8 Bicycle Touring Regions of Italy
- 13 Easy European Bicycle touring routes are a great way to see the area
- Finding Bicycle Friendly Accommodation in Europe can help with your planning
Final Thoughts: Bike tour in Tuscany
Tuscany has always been a popular destination and with good reason – numerous historical sights, hilltop towns, excellent food and wine, and great weather. Do not forget to take a Tuscany cycling guide, as there are a few signed routes. Your bike tours in Tuscany will be the envy of your friends.
