San Gimignano, home of medieval skyscrapers

A description of a short trip to San Gimignano in the Tuscany region of Italy.

When deciding where to visit on a trip to the Tuscany region of Italy, I had read a lot about San Gimignano. The words “over crowded” “disneyland-esque” “way too touristy” kept coming up in searches of previous visitors’ descriptions of the town. Other words were “magical” “must see” and “my favourite town of my trip”.

So I was conflicted. To go, or not to go …

After much debating, I decided I had to see the place for myself and the best way to see San Gimignano (as a whirlwind visit) would be to devote an evening to the hill town. The plan was to arrive after and leave before, the swarms of day trippers.

Even though it was out of the way (we were leaving Greve in Chianti, going to San Gimignano for a night and then turning around to go to Siena the next day), I thought the detour might be worth it. After all it was Italy, so how bad could it be?!

Arriving by car and finding a parking spot in one of the many parking lots (lots of spaces and this was in mid-September), we packed an overnight bag leaving most of our luggage in the car (NB: not recommended because of possible theft, but I was tired of carrying my big bag around by this point).

Finding the bus to the main gate (Porta San Giovanni) was easy and before we knew it, we were walking up the traffic-free main drag (Via San Giovanni) en route to our hotel for the night, Leon Bianco. I picked the hotel because I liked the idea of having a room overlooking the main piazza, Piazza della Cisterna. The Piazza gets its name from the underground Cisterna (cistern) that was built in 1287 that sits in the centre of the piazza. If you look up close, the sides of the cistern are worn out from hundreds of years of ropes wearing away at the stone from its use as a well. It’s hard not to get caught up in the history in a town like this one!

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Our room overlooked the Piazza della Cisterna

We loved our hotel (for the view, nothing overly special about the hotel itself), and the view overlooking the piazza. Though my favourite spot was sitting on the steps of the Cisterna, eating a gelato (more below) 🙂

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Piazza della Cisterna by day. The large crowd to the right is waiting in line for gelato at Gelateria Dondoli (the owner was a member of the two last teams to win the gelato world championship! Yes it’s worth the wait!). The Cisterna is just to the left.
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Eating the world famous gelato in front of the Cisterna. It doesn’t get any more San Gimignano than that! You can see the dimples on the rim of the cistern, worn down from the ropes used to gather water over hundreds of years.
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Three of the town’s remaining ‘skyscrapers’. The former wealthy families built large towers for their protection during raids and as a symbol of their wealth.
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Of the over 70 original towers, only 14 remain today. For being over 700 years old, they’ve stood the test of time fairly well.

In the evening, we walked up to a lovely park behind the Duomo following the signs to Rocca e Parco di Montestaffoli (stairs are to the right of the Duomo). At the far side of the park are (more) stairs to the top of a small tower which provides you will this view …

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San Gimignano at dusk = magical (in my humble opinion!)
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Another view of the town and neighbouring countryside
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Same view as above, but at dusk

For dinner we ate at Le Vecchie Mura, sitting outside on the terrace (we walked by earlier in the evening and made a booking for 8pm – the terrace was packed and we were happy we booked!). The meal was good, but not amazing, but the views more than make up for the food.

After dinner, we strolled the small town, at sat on the stairs of the Duomo, soaking in the beauty of the towers in the glow of the lights of the piazza. Blissful and the perfect end to a short, but awe-inspiring evening in the magical town of San Gimignano.

What are your thoughts on San Gimignano? Tourist trap or a favourite spot?

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