Hiking Around San Gimignano: A Search for the Best Views

Once upon a time, the small town of San Gimignano had as many as 72 towers standing to defend the city.

It’s hard to imagine now, when just 14 towers remain. Even with only a fraction of the town’s original towers still standing, San Gimignano feels like it’s full of towers.

When I visited San Gimignano one August, a primary goal for me was getting far enough away from town to get some great views of these towers and understand the place of the town within its surroundings.

To do that, I went on a lengthy hike through vineyards and fields and forests. Did I find those great views? You tell me!

In this post, learn all about my San Gimignano hike — including where I found my favorite views — and how to do it yourself.

Know Before You Go

The basis for my hiking route was this loop on 10Adventures. I followed it, for the most part — I did miss a turn and briefly went off in the wrong direction.

If you’d like to take this same hike, you can use the map on 10Adventures or follow the exact route I took, which is set out on the map below (though I recommend ignoring the weird little offshoot I took when I went the wrong way in the southeast corner!).

This hike does not follow an official trail of any kind — there are certainly no signs pointing the way at any moment — so it definitely is important to download (or otherwise be sure you have access to) one of these maps before you head out!

TIP: This map contains the hiking route discussed in this blog post. To save it to your own Google Maps account, click the star next to the map’s name. You can then find and use the map from your Google Maps app by going to “Saved,” then “Maps.”

Hiking Around San Gimignano

Here was my experience hiking out into the Tuscan countryside from San Gimignano.

Leaving San Gimignano

I set out from my lodging (outside the northern end of the walled city) a little before 7 am and walked through the quiet town, which would be full of tourists (and a few locals) within hours.

Just past the Porta San Giovanni on the southern end of the walled city, I found a small area with incredible views of the countryside surrounding the city. It was all I had ever dreamed Tuscany could be: rolling hills as far as the eye could see, with trees and stately old homes all glowing in the early morning light.

I turned left to head east at the first available opportunity, and started walking down a hill. As I journeyed down this road, I kept turning around because there were wonderful views of the town just behind me.

This was, by the way, the last half-decent lighting I had during my entire hike. As the sun quickly rose in the sky, the town was bathed in super harsh lighting. (This was more of a problem for photography and video than for my in-person experience; editing my photos from this hike was a difficult and atypically unpleasant task!)

Walking Away from Town

In order to get a good look at San Gimignano from afar, I had to walk a decent distance directly away from the town. So, after those initial great views of San Gimignano, I spent a few miles walking along roads (mostly quiet gravel roads, but some busy roads) and within trees with nothing interesting to see.

Through the Vineyards

Eventually, I stopped walking east and turned north. I began climbing a hill and found myself on a path along the top of a vineyard. Below and beside me were rows and rows of grape vines — and to my left, now several miles in the distance, was San Gimignano.

From here, I could see how San Gimignano is situated within its Tuscan surroundings — the towers scattered throughout the walled city, the sprawl of the town’s buildings around them, the small ridge behind the town, and the rolling hills below it, covered in lush trees and green and brown fields.

As I walked along the vineyards, I continued to admire this view, which shifted in small but noticeable ways as my position to the city changed.

Soon, I turned left onto the Localita Montefalconi road, and began to walk northwest. Here, in many places, the road had more open views in a variety of directions, which meant that I had good views not just of San Gimignano, but also of hilltop villas, more vineyards, and other beautiful aspects of the area’s surroundings. I also encountered farmers caring for their fields in tractors and and some people on ladders, harvesting crops from trees.

After 15 or 20 more minutes along this road, I had walked downhill enough that I could no longer see the hill that had previously served as a backdrop for San Gimignano. Now, the city’s towers stood tall and stark against a blue sky alone. These beautiful views of the town continued as I walked toward the northernmost point in my route.

Turning Back Toward San Gimignano

When I reached the SP127 road, I turned left and then headed southwest, back toward San Gimignano.

Along the way, I encountered a group riding horses — which, I admit, seemed more enjoyable than what I was doing at that moment (climbing up a hill in the late-morning August heat) — and got a few last glimpses at San Gimignano from a distance before I made my way back into town.

Final Thoughts

Oh man, I loved this hike.

Was every bit of it wonderful? No — most of it was along roads, and while they mostly weren’t busy roads, hiking beside cars is pretty much never great.

But were the views worth it? Absolutely. By getting some distance from San Gimignano, I could truly appreciate its hilltop position, its density of towers, and its incredible Tuscan setting.

pin this post