San Gimignano is Italy’s Medieval Manhattan with its skyline of fourteen stone towers rising dramatically from the Tuscan countryside. Originally there were 72 towers, some as tall as 50 meters, each built by San Gimignano’s patriarch families in a competition and display of their wealth. Seven of the remaining towers stretch up under the Tuscan sun around Piazza del Duomo. So what is there to do in Medieval Manhattan? Here’s our list of 7 things to do in San Gimignano:
A harpist plays at La Rocca
1. Explore La Rocca di Montestaffoli
Walk up the hill from Piazza delle Erbe to La Rocca di Montestaffoli, the ruins of the 14th century fortress above the town. Lovely olive groves provide a bit of shade from the sun and a great place to enjoy salami on a baguette while taking in the views of the rolling Tuscan hills and the towers rising from the town center. Roving musicians like the harpist pluck out classical tunes while artists set up their easels and paint. In summer, there is an outdoor cinema and you can learn more about Tuscany’s best known white wines at the Museo del Vino (Wine Museum).
Museo del Vino: open April to October Thursdays – Mondays 11am to 7pm and Wednesdays 3pm – 7pm. Admission is free and wine tasting is available for a small charge.
2. Climb the Torre Grossa
Torre Gross, the tallest tower at 54 meters (177 feet) in height and dating from 1298, is the only tower open to the public. Climb to the top for views over the picturesque countryside.
Admission is €5 and is included with the combo ticket for the Museo Civico.
Panorama viewpoint
3. Drink Vernaccia di San Gimignano
When you think of Tuscany, you probably think of Chianti. But the vineyards around San Gimignano produce the white wine grape Vernaccia, so famous it was even mentioned in Dante’s Inferno! Vernaccia di San Gimignano is a crisp white wine with citrus fruit flavors. Enotecas dot the medieval streets and you can even get a plastic glass to go, which you can take to one of the many panorama viewpoints to enjoy while gazing over the stone Tuscan farm houses and rolling green hills.
Piazza della Cisterna
4. Cool off with gelato
The world-famous Gelateria di Piazza is right in the center of Piazza della Cisterna and has a variety of creative flavors like saffron or pink grapefruit with sparkling wine. You’ll easily recognize it because there is always a line out the door.
5. Window shop
Shops and boutiques built right into the stone walls line the alleys of San Gimignano. You’ll find specialty food, wine, leather, and ceramic shops. Fine Italian leather can be found for much less than in nearby Volterra or Florence. Window shopping might tempt you to make a purchase and come home with two new leather bags like I did.
6. Buy wild boar salami
Gourmet shops all throughout San Gimignano sell local wild boar sausage. It even comes with red wine, truffles, fennel, or pine seeds and is thinly sliced and served on a crusty baguette drizzled with olive oil. Grab a salami baguette and a bottle of Vernaccia and head up to La Rocca for a picnic lunch.
7. Have dinner overlooking San Gimignano
Agriturismo Taverna di Bibbiano looks directly at San Gimignano and there is hardly a more romantic spot to sip on wine and have dinner while watching the sun set over the towers. The menu changes regularly based upon what ingredients are in season as everything comes fresh from the farm.
What are you favorite things to do in San Gimignano?
You can see all the UNESCO World Heritage Sites we’ve visited here. (Coming soon)
Jennifer Dombrowski
Jennifer Dombrowski is a location independent globe trotter and bases herself in Prata di Pordenone, Italy. She works as a social media and innovation strategist in higher education and is a regular contributor on johnnyjet.com. Her website, jdombstravels.com, is the 2012 Destinology Travel Bloggy Best Newcomer award winner. Google+
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We’re Jennifer and Tim and we love traveling! We are just one ordinary couple who have found that travel brought us closer together, taught us patience, the art of compromise, and how to truly appreciate the diversity of this extraordinary world. So far, we've visited 37 countries, lived in the United States and Italy, and Tim has lived in Korea. And we do it all while both holding down full time jobs. 
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Andrea
March 2, 2013 at 5:21 pm (UTC 2) Link to this comment
Mmmm – love wild boar!
Andrea recently posted..Arrival On the Antarctic Mainland
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Jennifer Dombrowski Reply:
March 4th, 2013 at 2:26 pm
Wild boar is definitely delicious in any form!
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Shalu Sharma
March 3, 2013 at 4:35 pm (UTC 2) Link to this comment
San Gimignano seems absolutely stunning. These pictures speak for themselves. I like the idea of cooling off with gelato. The name of the shop Mela House is interesting. Mela in Hindi means crowds, maybe there is some sort of similarity.
Shalu Sharma recently posted..Holi – Festival of Colors
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Jennifer Dombrowski Reply:
March 4th, 2013 at 2:27 pm
I think so, Shalu! One tip I should have included in hindsight is to visit San Gimignano in the morning because the afternoon brought hoards of tourists on tour buses. It would have quickly become crowded.
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Ali
March 3, 2013 at 10:55 pm (UTC 2) Link to this comment
Eat gelato is one of the best things to do anywhere in Italy! This looks gorgeous, but then I think I’d struggle to find a part of Italy that isn’t beautiful.
Ali recently posted..The Documents of Travel
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Jennifer Dombrowski Reply:
March 4th, 2013 at 2:31 pm
Audrey Hepburn should have said “Gelato is always a good idea!” Italy is indeed beautiful and we hope to be back to San Gimignano to explore the wine road when the wineries are open. They close up from November – April!
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Natalie
March 4, 2013 at 2:15 am (UTC 2) Link to this comment
Love these photos! Definitely makes me want to get back to Italy as quickly as possible!
Natalie recently posted..Eat: Sprinkles Cupcakes
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Jennifer Dombrowski Reply:
March 4th, 2013 at 2:32 pm
We hope you do come back for another visit and can explore more of Italy! Tuscany will be a must on your next visit.
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Wine Wednesday: Chianti Colli Senesi - Jdomb's Travels
March 27, 2013 at 10:25 am (UTC 2) Link to this comment
[...] vines for as far as the eye could see. We were in Strove, in the heart of Tuscany between Siena and San Gimignano, in the Chianti Colli Senesi wine [...]
Five Free Things to Do in Volterra, Italy - Jdomb's Travels
April 4, 2013 at 8:12 am (UTC 2) Link to this comment
[...] best preserved in all of Italy.Even still, Volterra is visited by far fewer tourists than nearby San Gimignano and worth a day trip when visiting Tuscany. Here’s our recommendations for five free things [...]