Gaiole Loop

Route Description for Gaiole Loop

Start on the pedestrian-only Via Bettino Ricasoli in Gaiole and walk roughly north, past the Co-op. Take your first right onto Via Baccio Bandinelli. At the T-intersection, go right. Go left at the second T-intersection. It’s a steep climb and the blood will get moving and you’ll heat up quickly.

Go up and over the first hill and down and up another. Ignore markings that may indicate taking a road on the right. Along the way you’ll pass the turn off for Riecine Winery, where you can book a tour. Riecine is a great stop for Sangiovese lovers, with a recent Chianti Classico receiving a 94 rating from James Suckling. As you climb you will pass olive groves and vineyards.

After about 2.0 km and a lot of uphill, you will come to an old brick and stone building. Don’t be surprised if you’re pretty tired by the steep uphill.

After a 3.3 km grind from start, you will come to a paved road. Go right and stay on this road for 140 meters then take the first left, signed to Badia Coltibuono. Immediately take a right and head down this road for 800 m. Do not take the dirt road on the right.

Badia a Colitbuono is a stunning 1,000-year-old abbey. It has cooking classes as well as wine and olive oil tastings. Check times and book in advance if you want a tour. Go to the far end of Bada a Colitbuono to get in.

Retrace your steps back to the main road and then immediately go across the larger road, onto a paved road heading uphill - Strada di Montigrossi.

At 5.7 km you will pass some abandoned red brick buildings. Soon after, look up to your left for another abandoned building, Castello di Montegrossi. From here you will quickly come to the cute little town of Montegrossi. Stay on the same road, all the way through town and it will turn back to gravel. At the first junction take the left-hand path, and then the next right at the next junction, signed for Montelucci.

At the third junction go right again. The gravel road feels tremendously remote here. Almost no sound and just peaceful tranquility.

At 8.3 km ignore the trail going up off the right. Stay on this trail named Barbischio Ensoli. 350 m later you will come to a T-junction, go right. Where the road splits 400 m, go right again, onto Via G Marconi. Continue along this road back into Gaiole and all the way back to the pedestrianized street, now a perfect place for a coffee or a glass of Chianti Classico.

Insider Hints for Gaiole Loop

• Gaiole is a pretty little town, though not very touristy. It’s a fun place to be based for a night.
• Gaiole is famous for the L’Eroica bike race, a 209.0 km bike race with almost 4,000 m of elevation gain. Most competitors usually take 15 hours to complete this challenging race.