San Gimignano Loop

Difficulty
This reflects the 10Adventures difficulty rating for each route. We aim to keep ratings consistent across regions.
Moderate
Duration
This reflects the estimated time the majority of users will take on this trail. If you are slower, add time to the top-end figure. If you are fast, then you may complete this route faster than this time range.
4.5-6h
Distance
This reflects the return distance of this route as measured by the GPS file.
17.0 km
Elevation
This reflects the total elevation gained throughout this route as measured by the GPS file. This includes all ascents and descents, and is higher than what is quoted in most route guides, which simply measure the distance between the starting-point and high-point of the route.
464 m
User Ratings
These ratings are completed by users who have completed this trail and not subject to reviews by 10Adventures.
Overall Rating
This is the average user-submitted overall rating on a scale of 1 to 10, with 10 being the highest.
9.8
Physical Difficulty
This is the average user-submitted rating on the physical difficulty of this route. In general, green is beginner, blue is intermediate, black is advanced/most difficult and double-black is expert-only. It is recommended that users build up to black and double-black routes.
Easy (Circle)
Suitable for beginners, families, young children, and those looking for a casual adventure.
Technical Difficulty
This is the average user-submitted rating on the technical difficulty of this route. In general, green is beginner, blue is intermediate, black is advanced/most difficult and double-black is expert-only. It is recommended that users build up to black and double-black routes.
Easy (Circle)
Suitable for beginners, families, young children, and those looking for a casual adventure.
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Directions to Trailhead
Beautiful architecture of San Gimignano on San Gimignano Loop Hike in Tuscany

The San Gimignano Loop is a quintessential walk through the Tuscan countryside. Walk through olive groves and past wineries, with stunning views all around. The San Gimignano Loop is a beautiful day out in Tuscany.

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Route Description for San Gimignano Loop

The San Gimignano walk is tricky, as there are no markings to help you find your way. This route has a lot of subtle turns, and it’s actually quite hard to follow with a text description alone. We suggest you have the GPS file downloaded and/or have a map on your smartphone that shows your position on this route.

Before starting, enjoy some time in San Gimignano. Stop for a cappuccino or a cornetto at one of the many cafés lining the street out of town. If you stand at the bar, a cappuccino is very cheap.

From Piazza della Cisterna take Via S. Matteo north out of town. Continue along this road until you cross SP1 to Via Niccolo Cannicci and then take a quick right on to Via Cepparelli. The walk out of town has amazing views of San Gimignano to the left side with vineyards in foreground.

Continue along this road until it becomes SP127. Stay on SP 127 until you reach a fork and take the road that veers to the right, getting off SP127 (do not take Via Cortennano which is a right turn). Continue on this road for roughly 1 km where you will come upon the Teruzzi Winery. You can get a guided tour of the winery, which includes a fine tasting.

Pass the winery and continue along Localita Casale for roughly 650 m as it curves to the right and you will once again approach SP127. Walk along the SP 127 for roughly 30 m then turn right onto Via Sant’ Andrea. Follow along this road for 1.5 km as it twists and winds through groves and forests. At this point there is an intersecting road to the right. Continue straight but the road name will change to Localita Montefalconi.

Continue along Localita Montefalconi for roughly 1.5 km. It will wind its way through several BnBs and the lovely Tuscan countryside. Just before the 1.5 km mark you will pass a good place to stop for a bite if it is that time of day - La Grotto di Fulignano. Enjoy a great meal with fantastic views of the Tuscan countryside.

From La Grotto di Fulignano, you will come to a small settlement where Localita Montefalconi will continue curving to the left, but you will take the road to the right at a T - junction. Follow this road for roughly 246 m and then there will be a small dirt path to your right. Go right here and continue along this unnamed road until you reach a T-junction, here turn left. After following this road for 450 m take a right. This will take you around the side of Geografico Wine Shop, a popular place to buy wines, olive oil, balsamic vinegar and meats.

At the next road take a right and it will bring you to the front of the shop and straight on to SP1, a fairly busy road. Continue along SP1 to The Pietrafitta Wine Shop and then veer to the small road on the right, getting off the busy SP1.

Follow along this road as it hugs the trees and passes olive groves. After about 1 km you will come to a fork in the road, continue hugging the trees to the right and you will curve around the main buildings of the Pietrafitta winery. At the next intersection, go left and then a quick right. Continue along this road until you are once again back on the SP1.

Take a right on the SP1 and then the next right on to Via Vecchia per Poggibonsi (this is across the street from the Ai Vecchi Tempi restaurant). This road will wind past a few restaurants, houses, B&B’s, and eventually back into San Gimignano.

Once you are back in San Gimignano, you can either follow the road back into the small streets of the town, or take the pedestrian staircase that leads to Piazzale Monternaggio and then into San Gimignano via the gate and onto Via San Giovanni. Continue on this road until you are back at the Piazza Della Cisterna, where you can return to Siena on the bus or keep exploring San Gimignano.

Insider Hints for San Gimignano Loop

  • San Gimignano is very busy between 9am and 5pm, get there early to beat the heat and the crowds.
  • This trail doesn't have any signs or waypoints on it, be sure to take a map and instructions with you. Part of this route is on busy roads, so be careful anytime you’re walking.
  • Staying in San Gimignano is beautiful, and should definitely be in your plans for one night at least.

Getting to the San Gimignano Loop Trailhead

Make your way to San Gimignano. From Siena it's around 50 min drive. Another option, you can take the bus nr. 130 from Siena to San Gimignano.

Route Information

  • When to do

    April - October

  • Backcountry Campsites

    No

  • Pets allowed

    Yes - On Leash

  • Family friendly

    Older Children only

  • Route Signage

    Poor

  • Crowd Levels

    Moderate

  • Route Type

    Loop

San Gimignano Loop Elevation Graph

Weather Forecast

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San Gimignano Loop Reviews

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