Working as a Backroads Trip Leader in Tuscany certainly has its perks. Besides the great food and wine, there is a fabulous cycling culture supported by an excellent infrastructure of well-paved and well-marked roads. Over the years I've created a list of my favorite rides in the region, some featured on our Backroads trips and others a combination of local favorites. Here are my top five bike rides that showcase the best of the idyllic and famous Italian region between Florence, Arezzo and Siena known as Tuscany.
1. Sette Ponti
Distance: 19 - 37 miles
Starting Point: Reggello
This ride is featured on our Chianti Bike Tour and is one of the gentler rides you can find in hilly Tuscany. It takes place on a beautiful road that follows a rolling ridge part way up the Pratomagno, a grassy stretch in the Apennine mountain range. The road is called Sette Ponti, which means Seven Bridges, in reference to the many streams that flow down from the mountains to the Arno River Valley below.
Start the ride in Reggello and head in the direction of Arezzo, staying on the Sette Ponti road (SP1) for as long as you wish. On our trips we ride to San Giustino Valdarno to stay at the magnificent Relais & Chateaux Il Borro, but you could ride this as an out and back or pedal all the way to Arezzo and take a train back. Along the way you can stop in Loro Ciuffena, a charming town that's often referred to as "one of the most beautiful villages in Italy." Feeling energetic? After Loro Ciuffena, turn left on a smaller road toward Faeto and enjoy a quiet climb with breathtaking views before descending down into San Giustino Valdarno.
2. Montefioralle Loop
Distance: 40 miles
Starting Point: Radda in Chianti
From the famous medieval town of Radda in Chianti, ride up to another Chianti League town, Castellina in Chianti. Enjoy the incredible views from a beautiful road on a rolling that ascends toward Panzano in Chianti. Just before reaching the town, turn off onto a road that narrows and becomes one of the true back roads of the famed Chianti area. Surrounded by olive orchards and sangiovese vineyards, challenge yourself to a series of short but steep ups and downs before reaching Montefioralle. Be sure to walk through the narrow cobblestone street that winds through town and spot Amerigo Vespucci's home with a 'V' above the door. Then enjoy the soaring downhill into the medieval market town of Greve in Chianti followed by a climb up to Panzano. On your way back to Radda, stop for lunch at Osteria Le Panzanelle in Lucarelli for an authentic Tuscan feast.
3. Epic Chianti Loop
Distance: 57 miles
Starting Point: Castelnuovo Berardenga
More than just a personal favorite, this is often a trip highlight for Backroads guests on our Tuscany Bike Tour. From Castelnuovo Berardenga, the town on the southernmost edge of the Chianti area, ride north and start the epic climb to Monteluco, through San Gusme. When you reach the top, consider stopping in the bar for an espresso or a shot of lacrime del cinghiale, a local liquor named after the local famed wild boar.
From there, descend through the picturesque village of Castagnoli and climb up to Radda in Chianti. You can stop here for lunch--Bar Dante is a local favorite. Or grab some Tuscan specialties at the Casa Porciatti deli and picnic in the park where you can refill your water bottles at the brass fountain. After lunch, continue on to Castellina in Chianti, where you can stop for a gelato if you'd like, before cruising south of town and turning off toward San Leonino--one of the sweetest downhills around! At the bottom of the hill, climb back up to Quercegrossa and enjoy some spectacular views of Siena before a nice rolling road back toward Castelnuovo Berardenga.
4. Crete Senesi
Distance: 26 miles
Starting Point: Castelnuovo Berardenga
Another ride featured on our Tuscany Bike Tour, with its sweeping views and sense of movement, is always a favorite of both Backroads Leaders and guests Start in Castelnuovo Berardenga where you descend through vineyards and olive orchards before rolling through Montaperti, a town known for a historic battle between the rival cities of Florence and Siena. Stop at Bar Ricci in Arbia for a quick espresso before embarking on the magnificent Crete Senesi road (SP 438) where you'll continue for about 12 gorgeous miles. Be sure to stop and take pictures - the city you can see in the distance is Siena!
At the end of this stretch lies the quaint town of Asciano where you can reward yourself with a well-earned gelato. From here continue on to Borgo Casabianca, once a self-sustaining village but now a charming countryside hotel. If you're on a Backroads Trip this incredible place will be your home for the night! Otherwise, pedal on to hilltop town of Sinalunga, where you can catch a train (even with your bike!).
5. Val d'Orcia Loop
Distance: 34 miles
Starting Point: Bagno Vignoni
This ride is also featured on our Tuscany Bike Tour and hits the highlights of the spectacular Val d'Orcia area, whose agrarian beauty has earned it UNESCO World Heritage status. From the thermal bath village of Bagno Vignoni, climb to Pienza, the architecturally famed home of Pope Pius II. Take in the sights as you stroll through the streets lined with shops selling pecorino cheese. You're in the Tuscan production hub of this sheep's milk cheese!
Climb up to the medieval town of Montepulciano and reward yourself with a glass of the famed vino nobile di Montepulciano and lunch with panoramic views at Caffe Poliziano. Close the loop by riding past Montichiello, keeping an eye out for the white chianina beef cattle as you soar down a curving, cypress-lined slope. Still have energy? Add a challenging extension by climbing up to Campiglia d'Orcia - taking you part of the way up the tallest peak in Tuscany, Monte Amiata!