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San Gimignano – The Manhattan of Tuscany

  • 29/08/2021
  • Eric Whitehead
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Being unable to travel and enjoy different parts of the world has been very difficult. It is discouraging that it doesn’t seem to be getting better anytime soon but we live in hope that someday in the not too distant future it will be safe and possible once more. In the meantime my wife and I are fortunate to have a long list of stories from past travels. With that in mind we turn the clock back…

The drive from Siena to San Gimignano was very relaxing though not overly scenic and only about 40 kilometers. My first view of San Gimignano in the distance made me feel like a kid at Christmas. Oh how this awesome town beckoned me!

Once again, finding the town was not difficult, thanks to Gianni’s tip at Monteriggioni; finding the hotel, well that’s different. Thank goodness Karen has a knack for getting through to people for directions no matter what the language.

The hotel we selected was just three kilometres from San Gimignano, a UNESCO World Heritage site since 1990. Nestled in the Tuscan countryside among centuries-old woods, olive groves and vineyards, it never ceased to provide us with a stunning view of the city on the hill from our top floor room. The hotel was created through the renovation of a Tuscan farmhouse complete with an ancient watchtower. Though rural in its features it was very modern in its comforts.

In Medieval times San Gimignano boasted 72 towers. Ancient wars resulted in the destruction of some, and the fact that some were higher than the church steeples necessitated that they be razed to the ground, leaving 14 standing today. It is a truly awesome sight and one can easily see how the nickname “Manhattan of Tuscany” came about.

The city sits on the ridge of a hill and is encircled by three walls with the ruins of a fortress at its highest point. The eight entrances into the city are set into the second wall which dates from the 12th and 13th centuries. San Gimignano certainly maintains its medieval appearance and almost allows you to walk back in time on a visit.

After our effort in Siena we just had to climb La Torre Grande for the supreme view of San Gimignano. The climb was not as difficult as the one in Siena. The passageways were a little wider but still a tight fit for my Michelin frame.

Sunrise over San Gimignano pretty much made up our minds that we would stay another day and return to the city. Before heading into the city we took some time to just stroll around the grounds of the hotel. It really is a lovely place. We ventured into the vini on site. The old fella was happy to see us, to see anyone I think. I guess it’s a little slow here in the shoulder season. I have no idea what he said to us but I believe it had something to do with the fact that the bottle of wine I bought was from his vineyard. I’ve sampled many wines on this trip and it has all been wonderful. I favour the reds but Vernaccia di San Gimignano is one of Tuscany’s oldest and noblest white wines.

On our return to San Gimignano, as was the case in Siena, we saw a lot more the second time around. I had read that the view from the fortress is not to be missed. So, we climbed the hill behind the Duomo to see what the fuss was all about. Well worth the effort. In this town, different angles on the towers yield very different results.

The Duomo, which is present in every Italian town, is usually the centre piece of the town. I love them because they’re all different and all fascinating. Sadly one thing that is not different is that many of them are being renovated and the surrounding construction does not compliment any photos. Nevertheless, a last stroll through the town confirmed we really did love it. This is one of the most unique towns you will ever see.

We returned to the hotel in time to relax before dinner. For me, relaxing entailed sitting on the balcony with a bottle of wine, writing my journal and gazing longingly at the city on the hill.

Before going to dinner we tried to find a grocery store. A fruitless pursuit; I believe the Coop sign we saw refered to a store in Switzerland. On our return we were stopped by La Policia. I have no idea why. He pulled me over with the wave of a small sign. Was I speeding, breathalyzer, what? I said, “Hello. How ya doin’” He had that “Forget it, I can’t be bothered with this” look on his face and waved me on through.

Our final dinner in San Gimignano was out of this world. The food in Tuscany has been amazing; both Karen and I raved at how awesome it was. She had the bread soup with vegetables and I had tortellini with meat sauce (rapidly becoming my favourite dish), steak, thinly sliced in Tuscan sauce, then pan fried in olive oil, then served with onions, peppers, tomatoes and lemon. An absolutely incredible meal supplemented by a mandatory glass of San Gimignano vino rossi.

We decided to leave San Gimignano even though I could have sat on the balcony and stared at the view for another week. You can get everywhere we’ve been and then some in two hours or less from San Gimignano. It truly is the heart of paradise in Tuscany. We will return someday – for that view alone.

Much more travel writing by this author in his book, That Road Trip Book.

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