Best Bike Trips in Tuscany
Credit: Alamy

The absolute best way to see Tuscany is on foot because you don’t miss even a step of the beauty. The second best is by bicycle. Riding a bike in Tuscany—as many things in Italy—is an exercise in yin and yang: the best with the worst. If you’re a mountain biker it’s all yin: the terrain is hilly enough to be fun but not so steep as to blow up your lungs. Plus, the most beautiful parts of Tuscany are its completely deserted back roads, most of them unpaved but perfect for wide tires.

If you’re a road biker—with thin, racing wheels—things get a bit yang-y. On the yin side, bicycle racing and road touring is Italy’s favorite sport (after calico, soccer), meaning that drivers of cars are very used to sharing the road with bikes. On the yang side, I’m not sure Italians have ever heard of bike lanes—if they had, they made damned sure they forgot about it at once. This is not a problem on deserted back roads, but not very calming when you’re sharing a steep main road with cars and your heart is beating at 200 rpm.

So there you have it.

As for how you travel—completely on your own or with an organized tour—that’s a personal choice. You should not fear getting lost as long as you have a good map and compass because signs are everywhere, and every farmhouse has a name that’s indicated on hiking maps. The drawback of being on your own is—that unless you do daily out-and-return trips—you’ll have to lug all your worldly possessions with you. This is where the tours come in handy. They organize your hotels, meals, sightseeing, and wine tasting, but, more importantly, they move your stuff from place to place while you ride around happily with only the sun on your back.

For these reasons, I broke the 5 tips into two groups: one is the tours offered; the other is two of my favorite day trips where you can easily—meaning little traffic and no heart attacks—bike on your own.

DuVine Tuscany Bike Tour

This is an international company that coddles you through a six-day, five-night bike tour of the most gorgeous parts of Tuscany. The level is active, with average day rides of about 25 miles. They not only move your stuff and put you up at first and luxury-class hotels, but also take you to the best sights, restaurants, and even wine tasting. You’ll cover the medieval hill towns: Pienza, Montepulciano, Petroio, Montalcino, Siena, and all the amazing countryside in between, as well as a day in the Chianti region. Pricey, but unforgettable.

Tuscany Bike Tours

This tour company, covering Florence and the nearby Chianti hills, offers one-day bike tours that are the ultimate in luxurious sightseeing. Only thirteen miles in seven hours (although there is one loooong hill climb), they take you to wine tasting, olive oil tasting, and a visit to a castle with a real-life count and countess.

They also offer three-hour tours, morning or evening, of Florence and its surrounding hills (about eight miles). Lastly, they offer unaccompanied bike rentals—three-speed, comfy seats, by the hour, day or week—so you can peddle around Florence to your heart’s content. Florence does have some bike lanes, so you won’t feel like a gladiator.

I Bike Tuscany

A company started ten years ago by passionate bike racer Marco Vignoli, I Bike Tuscany offers tours around Florence and the Tuscan hillside but with a wonderful on-demand twist: electric bikes. If you haven’t tried one, they are a riot. At normal peddling, it’s a bike, then when you start to struggle, wham, the little motor kicks in and you’re off. This is most handy in the hilly terrain of Tuscany. And they are flexible. They offer carbon-fiber road bikes or twenty-four-speed mountain bikes. Plus, they’ll arrange the tour wherever you want, including pickup and drop-off at the places of your choice. The guides are personable and enjoying-life friendly.

True Tuscany

If I had one last bike trip to take, this would be it. It’s mostly empty, unpaved roads with unlimited views, and stops at castles, a monastery, and Tuscany’s best medieval town. You can start this loop anywhere but I’ll go from San Quirico d’Orcia. Follow the Old Cassia road north (paved), toward Torrenieri. After 1.86 miles, turn right at the sign for Cosona. The road is unpaved from here for quite a while. After a short climb, you’ll have a breathtaking view on your right of the entire Val D’Orcia (a World Heritage region) with the great volcano beyond. Bike on to Castello di Cosona and feel free to walk around. A couple hundred yards past the castle, turn off and walk out past the ruin and a pond to another ruin with the world’s best view. Back on the main dirt road for a little over 3 miles, you hit paved road. Turn left for about ½ mile to the medieval monastery of Sant’Anna in Camprena where The English Patient was filmed. Ogle. Backtrack on the paved road all the way to Pienza (most beautiful medieval town). Take the back road to the cemetery, join the main road toward San Quirico d’Orcia. Descend beyond the left hairpin turn, then at the bottom of your descent, where the paved road straightens to the right, turn off left onto a dirt road. Follow a dirt road back to San Quirico.

True Tuscany

A beautiful loop with lots of worthwhile stops in tiny medieval towns. From San Quirico, take Old Cassia road to Torrenieri. Go on to San Giovanni D’Asso, a charming tiny town with an old section and a small Romanesque church. Head back down the hill, then turn left to Montisi. After a bit of a climb, you’re on a gorgeous ridge with views on both sides. From Montisi, go to Castelmuzio (great lunch in town’s piazza). From here, you can take an eight-kilometer side trip to another medieval town, Petroio and back, or go towards Pienza, with a stop at the monastery of Sant’Anna in Camprena. From Sant’Anna, on to Pienza, and from Pienza, back to San Quirico.