Perched on a hill between Florence and Siena, watching over the fields and vineyards, San Gimignano is the perfect medieval town.

Piazza-Cisterna-San-Gimignano

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10 Things You Absolutely MUST Do In San Gimignano

1. Visit the Duomo.

the view from my apartment window, looking over the Duomo

The Duomo is in the heart of town, so you can’t miss it. It is world famous for it’s spectacular fresco cycles dating back to the 13th century, with works from Domenico Ghirlandaio, Benozzo Gozzoli, Taddeo di Bartolo, Lippo Memmi and Bartolo di Fredi. The basilica is located within the UNESCO World Heritage Site of the “Historic Centre of San Gimignano”, with its frescos being described by UNESCO as “works of outstanding beauty”.^[2]

2. Eat an artisanal gelato.

Late night gelato in Piazza Cisterna, San Gimignano

The gelato store in the neighboring Piazza Cisterna makes fresh gelato each day in a variety of sensational flavors. Try raspberry with rosemary, or any flavor with lavender. Actually, it’s probably impossible to find a flavor that isn’t fantastic. Sometimes there are lines across the piazza with locals waiting to get a scoop or two of this delicious homemade gelato.

Wander back through to Piazza Duomo and sit on the steps while you eat your gelato. Look up and you will see my apartment looking right back at you!

3. Walk down to the medieval font.

one of my travelers in June 2016 exploring the font on a rainy day

The history of this idyllic mountain town is just wonderful and there is just so much to see! Most people don’t make it down to the font. Everytime I have wandered down there we (whoever is with me) are the only people there having a look. I think most people don’t even realize its there.

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4. Take a stroll.

You can walk around San Gimignano forever and not get bored. The light hits the walls and the towers differently every minute of the day, so it always looks new.

Wander through the medieval arches and alleyways, explore the little piazze, window shop and walk from one end of town to the other. Meander off the main shopping streets and explore ll the little neighborhoods. San Gimignano is just beautiful!

wander around in the evening for a different view of the town.

5. Walk the wall.

walking along the wall in San Gimignano, summer 2016

The views from the walls of San Gimi are absolutely breathtaking. A glass of local Sangiovese in the late afternoon at one of the little restaurants along the wall, with a view of endless vineyards, olive groves and fields that have been farmed by the inhabitants of this town for centuries. The view is so lovely it will stay with you forever…

late afternoon glass of wine along the wall, taking in the view in San Gimignano

6. Visit iSculpture San Gimignano

This one is a fantastic find in a region full of historical sculpture my friends Francesca and Patrick have built a tremendous business and a wonderful gallery featuring only contemporary art created by Italian artists.

The works are fresh and exciting and new, and make for an all encompassing experience housed in an ancient, historical building. The gallery is deceptively huge, and is the perfect showcase for both small and gigantic pieces. It’s one of those places that keeps drawing you back in.

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7. Climb the rock at sunset.

The highest point of town at the San Matteo end affords you the craziest, most sensational views as the sun goes down. Climb the stairs up to the top of the fortress and take in the absolute splendor of Tuscany, as far as the eye can see. Walk the inner wall at the bottom of the steps and look through the window-slits where for centuries local soldiers guarded the town and fired arrows at attackers. You can imagine them sitting watch, taking in the sunset, and wondering if they would be under siege this night.

8. Eat Pizza at Il Trovatore

Summer evenings spent on the patio at Il Trovatore with pizzas cooked in their giant wood burning oven and jugs of local wine just cannot be beaten.

Tuscan pizza is nothing like American pizza. It is fresh and light and explodes with flavor. Don’t expect it to be drenched in tomato sauce and wallowing in melted cheese – this is pizza the way it was meant to be eaten!

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9. Enjoy Prosecco in the Piazza

late afternoon spritz and prosecco in the Piazza Cisterna, San Gimignano

My favorite time of day is “prosecco o’clock” in the piazza. The late afternoon/early evenng glass of prosecco that you enjoy sitting at one of the outdoor restaurants that line the piazza, watching the early evening light hit the walls of the palazzi, as the tourists leave and the locals come out.

Its absolute magic.

10. Be there for market day

buying fresh local cheeses and prosciutto at the San Gimignano market

Every Thursday morning San Gimignano wakes up to market day. The market takes up all of Piazza Duomo and Piazza Cisterna.

the local ladies buying their fruit and vegetables at the weekly market

From local cheeses and meats, to fruits and vegetables, from Italian leather handbags and belts to clothes and shoes, from fabulous Italian linen tablecloths and napkins to housewares, there is so much to look at and buy!

Plan on  buying lunch from one of the food trucks and eat it sitting on the Duomo steps.

The leather handbags are the same as the ones you will find at the San Lorenzo Market in Florence. I have always found them to be cheaper at the san Gimignano market. Expect to pay between 35 and 50 euros for an incredible Italian leather handbag that will last a lifetime.

I hope you take time to go visit San Gimignano – it is so lovely!

Need help planning your trip to Italy? Check out my international best selling books Glam Italia! How To Travel Italy (Secrets To Glamorous Travel On A Not So Glamorous Budget) and Glam Italia! 101 Fabulous Things To Do In Rome. Both books are available worldwide on Amazon.

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