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San Gimignano Loop Walk

· 3 reviews · Hiking route · Italy
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  • Views of San Gimignano as you leave for today's walk
    Views of San Gimignano as you leave for today's walk
    Photo: Sally Thompson, Macs Adventure
m 300 200 100 14 12 10 8 6 4 2 km
Venture out of San Gimignano into the patchwork landscape of vineyards and woodland for a rewarding loop walk.
Distance 15.7 km
5:00 h
451 m
451 m
332 m
98 m

Vineyards as far as the eye can see on this beautiful walk with almost immediate stunning views of San Gimignano as you descend out of the town into the surrounding countryside. Walk through small residential hamlets before coming to a wine shop. After this enter deep into wine country with quiet country roads meandering through picturesque vineyards and even passing part of the ‘Strada del Vino Vernaccia di San Gimignano’, an area which produces the famous ‘Vernaccia’ dry white wine.


Author’s recommendation

Do not miss a visit to the Geografico wine shop. Hopefully it will be open the day you are there. Here you can not only sample the wine but also purchase some should you wish. In particular try the Vernaccia white wine which is famous in this area.
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Macs Adventure
Update: September 26, 2022
Highest point
332 m
Lowest point
98 m
Best time of year

Track types

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Safety information

You will be walking along rural roads and trails. The rural roads are quiet but nevertheless, please be careful to take care of any traffic that may pass by.

Tips and hints


Food & Drink ...

A lovely place to stop for a ‘light lunch’ is the rural farmhouse at Fattoria Poggio Alloro. Relax and soak up the views of San Gimignano from the terrace as you feast on bruschetta, pasta, fresh green salad, pecorino cheese, prosciutto, salami, red and white wine, rounding off with a  sweet taste of vin santo and cantuccini biscuits. (Please check opening /closing times)  Take your time winding the 5km back to San Gimignano.

Alternatively you can purchase provisions for a picnic lunch in San Ginignano before you leave should this fattoria not be open on the day you are there.


Some useful links ...


Strada del Vino Vernaccia di San Gimignano:  This is a non- profit organisation that was founded in 1999 by local wine producers and enthusiasts to promote the local white wine producing territory in tourism as well as to protect the quality and integrity of the vernaccia wine of San Gimignano. This is a wine road which simply means the area has a high concentration of vineyards producing a particular kind of wine. In this case it is Vernaccia- a famous and protected dry white wine which can be a nice change for white wine fans amongst all the Chianti red wine mania of Tuscany!


 (This route is used in the following itineraries: WItSClass)



San Gimignano Tourist Information Centre (332 m)
43.467674, 11.043203
43°28'03.6"N 11°02'35.5"E
32T 665271 4814779


San Gimignano Tourist Information Centre

Turn-by-turn directions

0.00km - START POINT: Tourist Information Centre. With the Tourist Information centre directly behind you head right and then TURN RIGHT onto Piazza della Cisterna.Continue STRAIGHT ON walking onto Via San Giovanni descending.

0.50km - Exit Historic Centre through Porta San Giovanni. BEAR LEFT onto pavement. There is a nice bakery here which is an ideal spot to pick up some lunch for the day ahead.

0.65km - BEAR LEFT down stone steps leaving main road and the Piazzale on your right. Join pavement BEARING LEFT. Ignore sign on your right for Via Francigena. Continue to BEAR LEFT onto Via Vecchio, a small asphalt road. 

0.85km - The road soon changes from asphalt to gravel; continue on STRAIGHT ON  descending slightly. You will be passing private houses and small guesthouses. There are stunning views of San Gimignano to your left. 

2.30km - Pass sign and road on right for Agriturismo Sovestro. Ignore and continue on main gravel road BEARING LEFT and descending.

2.75km - Arrive at Junction. TURN LEFT onto main road and walk alongside road on grassy bank where possible. Take care as this road is quite busy. 

3.00km - After approx. 250m, TURN LEFT again onto small gravel road leaving the main road behind you. You will see a road sign for P. Della Costa. Ascend steeply. 

3.60km - Ignore guesthouse signage and continue STRAIGHT ON  on main gravel road ascending and following the hairpin bends.

4.00km - BEAR LEFT on main gravel road, ignoring faint grassy path on right. Continue STRAIGHT ON  ascending. After approx. 10m, come to a junction. Ignore road on right signposted for La Paternita. Continue to BEAR LEFT. Almost immediately after, arrive at another junction and TURN RIGHT.

4.70km - BEAR LEFT and ignore road on right signposted for F. Pietrafitta. Descend passing building ruins on your left. 

5.50km - Continue STRAIGHT ON descending and ignoring small road on right. There is a vineyard to your right.

5.90km - Come to junction, TURN LEFT onto main asphalt road and walk alongside road. Take care as it can be quite busy.  

6.50km - BEAR LEFT and come off main road at winery/wine shop ‘Geografico’. Join smaller asphalt road here and continue STRAIGHT ON. After about 20 meters and at the end of the small asphalt road, TURN LEFT, walk around gate onto gravel track, you will have a ruined building in front of you. Continue on narrow dirt track with the ruined building now on your right.

7.00km - After crossing small bridge continue BEARING LEFT on dirt track, leaving small allotment on your behind left.

7.50km - BEAR RIGHT at fork in dirt track, ascending towards tree line. Ignore track straight ahead. 

8.00km - Come out of wooded section on track and BEAR RIGHT with a vineyard on your right. Continue on dirt track ascending. After a few meters ignore faint grassy path bearing right and continue STRAIGHT ON now with vineyard and views to San Gimignano to your left.

8.50km - Ignore faint grassy path on left and BEAR RIGHT continuing on path and ascending.

8.60km -  At top of hill, come to junction. TURN LEFT onto small gravel road.

8.90km -  Arrive at another junction. There is a villa directly in front of you. BEAR LEFT and continue, the road here is asphalt for a short stretch. Pass a small church on your left and descend on gravel path.

9.50km - Ignore small gravel path bearing left and remain on gravel road following as it meanders and descends. Ignore any small side paths and remain on this gravel road as it meanders and undulates for just over 3 kilometres.

12.90km - Arrive at a junction, you will see a road sign for San Gimignano. TURN LEFT. Follow faint grassy path adjacent to road with vineyard on your left.  

13.20km - Come to end of faint path and TURN LEFT onto small asphalt road descending, following the sign for Ponte a Ronoldino.  

14.00km - BEAR RIGHT onto now gravel road ignoring gravel road on left. There is a modern warehouse on your left. Shortly after, cross small bridge and BEAR LEFT, continuing on gravel road and ascending steeply.

15.20km - Arrive at a junction. Join main asphalt road at junction and BEAR LEFT. The road is not too busy but there are some cars so do take care. Before doing so, there is a nice wine shop/vineyard on your right that offer free wine tasting and the staff here are very informative. It is an ideal place to pick up a bottle or two as you are nearing the end of your walk.

16.30km - Arrive at busy junction. Cross very carefully and continue STRAIGHT ON  onto small asphalt road (Via Garibaldo Cepperelli- you are now in the suburban area of San Gimignano). Shortly after, come to small roundabout with large tree and stone in the centre. TURN LEFT onto Via Vincenzo Tamagni, then LEFT AGAIN to continue on Via Vincenzo Tamagni. Shortly after this, come to a junction, cross road on zebra crossing. Take care as this is a busy road. Join path and TURN RIGHT to have the city walls on your left.  

16.90km - BEAR LEFT and enter the historic centre through the Porta San Matteo, continue on Via San Matteo ascending gently. At top of Via San Matteo, come into Piazza del Duomo. Walk across the square to return to your start point: the Tourist Info centre. 

17.20km - FINISH POINT: Tourist Information Centre.


all notes on protected areas


43.467674, 11.043203
43°28'03.6"N 11°02'35.5"E
32T 665271 4814779
Arrival by train, car, foot or bike


Please be prepared by taking all necessary items. For example, proper rain gear (jacket and pants) and a sun hat and sunscreen (particularly essential during the hotter months).

Questions and answers

Question from Becca Blacknell · February 02, 2020 · Community
Hello, would it be possible to do this tour via bicycle?
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Answered by Emmerentia De Goede · February 03, 2020 · Community
Hi there, I am not an expert cyclist, but there is about a 2 km uphill, very sandy, single tract part of the road which would be impossible to cycle, in my humble opinion.


Thorsten Smija
November 03, 2022 · Community
Wenn Sie wissen wollen, wieso die Autos in der Toskana immer so staubig sind, nach dieser Tour wissen sie es. Einfallslose Wanderung entlang der staubigen Zufahrtsstraßen diverser Agritourismus-Unterkünfte. Nicht zu empfehlen.
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When did you do this route? October 31, 2022
Nicole Weisenberger
April 25, 2018 · Community
Tolle Wanderung. Schöne Wege auch mal kurz auf Staatsstrassen. Ansonsten wunderschöne Landschaft. Dank GPS kein Problem den Weg zu finden. Wir sind in San Gimingiano am oberen Tor losgelaufen weil da ein Parkplatz ist.
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Mittwoch, 25. April 2018 21:11:41
Photo: Nicole Weisenberger, Community
Mittwoch, 25. April 2018 21:12:36
Photo: Nicole Weisenberger, Community
Mittwoch, 25. April 2018 21:13:25
Photo: Nicole Weisenberger, Community
Mittwoch, 25. April 2018 21:14:19
Photo: Nicole Weisenberger, Community

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+ 6

15.7 km
5:00 h
451 m
451 m
Highest point
332 m
Lowest point
98 m
Circular route Scenic Refreshment stops available Cultural/historical interest


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