10 Things To Do In San Gimignano

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




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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Corinna B’s World Goes To San Gimignano ~ The Glam Italia Tour

San Gimignano, Tuscany

 San Gimignano is my home in Italy.
Nestled on a hilltop between Florence and Siena, this little, walled, medieval town is known as the “Town Of Fine Towers”, due to the unforgettable skyline created by the remaining 14 towers that proudly watch over the neighboring hills and vineyards stretching their way across Tuscany. At one time there were more than 70 towers in this tiny town, playing an architectural game of “my one’s bigger than yours”.



 I just adore this beautiful place.






Buy local olive oils and cheeses in San Gimignano



At home in America when my crazy life gets too stressful, when I can’t sleep at night, or when life gets too complicated, I close my eyes and make the drive from Poggibonsi, through all the roundabouts, and up the winding hill, past the olive oil stand and the wineries, and in to San Gimignano.

My parking spot sits beside a giant nespole tree which bares the most beautiful fruit.

From there in my mind I walk to the Porta San Matteo and take in every store and coffee shop along the via San Matteo, sometimes stopping at Lucia and Maria’s for my daily caffe and slice of Mandorlata, sometimes just walking straight to the lovely Piazza Duomo and my beautiful attic apartment.
It is the quintessential de-stresser.

Grab a caffee and a slice of panforte at Lucia and Maria’s on via San Matteo


Thursday morning market in San Gimignano


Market day in San Gimignano, Tuscany

I love the Thursday morning market in Piazza Duomo and Piazza Cisterna



Enjoy a prosecco in Piazza Cisterna after the tourists have gone for the day
Enjoy a gelato or just chill at Piazza Cisterna, The cisterna was built in 1287

Take time to look inside the cisterna, There are deep grooves in the stone rim from centuries of ropes hauling up buckets of water.


Make sure you explore the back streets of San Gimignano

If you ever come to  San Gimignano, make sure you stay until after all the tourist buses leave at 5pm. Enjoy an early evening Prosecco in the Piazza Cisterna and take a sunset walk along the top of the walls that encircle the town. Take in the view, and breathe in the magical air of one of the loveliest places I know.


Piazza Cisterna in San Gimignano before the tour buses arrive in the morning



Via San Matteo in San Gimignano before the tour buses arrive


San Gimignano is magic at the end of the day when the tourists are gone
Stroll along the walls when all the tourists have left for the day

All images are my own. Please do not use without my written permission.

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10 Things You Absolutely MUST Do In San Gimignano

Where To Stay In Tuscany

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Where To Stay Under The Tuscan Sun

Thinking about spending some time under the Tuscan sun??

Podere Cunina standing watch over the Val D’Orcia

Every year I like to spend a few weeks in Italy.
Actually I would like to spend endless months there, but have to settle for weeks instead.
Tuscany has become my home away from home.

People always ask me where to stay in Tuscany, especially if they are not seeking out an overly homogenized hotel experience.
Personally I love to rent an apartment, rent a car and drive around Tuscany, finding endless spectacular towns and villages that aren’t in the guide books.

Podere Cunina, Buonconvento, Tuscany

I like to be super close to Florence, and not too far from Rome. In a country with such a fantastic rail system, I like to be close enough to a train station that it’s easy to make a last minute day trip to Venice, or maybe Pompei – wherever feels like fun that day.

one of the patios at Podere Cunina, Buonconvento, Tuscany

I like to chill out in the piazza, drink cappuccinos and watch the world go by. Shop at local markets for fresh produce,all grown inside a 10 mile radius and picked to be sold today, with flavor that just explodes in your mouth. (Unlike the flavorless factory farmed produce here in the US)
There’s nothing quite like having a local vendor choose items for you, and tell you how to prepare them the way generations of their families have been doing for centuries, and then going home to your gorgeous Tuscan apartment, throwing it together and enjoying it, truly enjoying it with a local Sangiovese, or maybe a Brunello, living the luxe life.

I love filling my Italian apartment with freshly picked wildflowers and sprigs of fresh rosemary, the combined olfactory delight of which tells my brain I’m really, truly here.

My dear friend Silvana is living the life I dream of.
Together with her husband Piergiorgio she bought an old, run down farmhouse on a little hill overlooking the spectacular Val D’Orcia. They rebuilt, refurbished and restored it using traditional materials, creating a home that at the same time is visually mesmerizing, maintains historical truth but is equipped with all the modern conveniences. Its called Podere Cunina.

Beautiful Podere Cunina in Buonconvento Tuscany

The stonework, the iron work, the colors are achingly beautiful.

Part of the restoration project involved creating 7 apartments to rent to vacationers.

One of the apartments at Podere Cunina, Tuscany

Apartment at Podere Cunina, Tuscany

Apartment at Podere Cunina, outside Buonconvento Tuscany

Apartment at Podere Cunina

 There are 2 two bedroom apartments and 5 one bedroom apartments, each of which is just gorgeous.

Apartment at Podere Cunina, Tuscany

Podere Cunina is located 3 kms outside of Buonconvento, near Siena. An easy drive from either Rome or Florence it places you in the ideal location from which to drive around Tuscany and really experience the majesty of this amazing part of the world.

After a long day of enjoying yourself it is just lovely to sit out on the patio area and have a prosecco as you watch the sun set over neighboring Montalcino (one of my favorite villages in all of Italy).

The pool at Podere Cunina, near Buonconvento, Tuscany

 Wine lovers adore the region, as it is home to the Brunello, one of my all time favorite reds.

Prosecco time at Podere Cunina as the Tuscan Sun sets

Silvana is the ultimate host. She always has loads of ideas of great places to go see and experience. She always tells me about fabulous villages that the tour buses (thankfully) don’t know about, is endlessly knowledgeable about where the best local markets are and when, which restaurants and cafe’s you mustn’t miss, and has the most wonderful stories about this spectacular slice of the world.

Lovers of Frances Mayes’ Under The Tuscan Sun, and her subsequent tomes about her life in Tuscany will love driving to Cortona, which is not too far away, and spending the day walking through every moment in her delicious Tuscan world. (I think at this point I probably know her books by heart)

3 million years ago the Val D’Orcia was under the ocean, which is no doubt why the hills have the most beautiful undulating roll to them. A couple of years ago some guests were walking through the fields on the beautiful Podere Cunina property and picked up a perfectly formed shark’s tooth, that scientists later dated as being 3 million years old.
You just never know what you’re going to find in this wonderful place!

Summer is not the only time to enjoy Tuscany. Spring and autumn are beautiful, and this year if everything goes as planned we are hoping to touch down in Tuscany over the winter too.

If staying on a glamorous little farm is a bit to rural for you, Silvana also rents out an apartment in beautiful San Gimignano, which is my Italian home, and which I can never go a single day without thinking about.

If you would like to know more about Podere Cunina or about vacation rental in Tuscany, click this link:
 Agriturismo Podere Cunina