Exploring the Medieval Manhattan: San Gimignano

During the summer, the old town is quite a tourist hotspot in the middle of the day with day trippers but from five in the afternoon, it is free and beautiful once again. Take a stroll through town stopping at the various ceramic, linen and pecorino shops, help yourself to an aperitivo in the Duomo square or Piazza della Cisterna. Make sure to then climb up the Duomo tower for a surreal view (and to help make space for more food).

Also worth visiting in town are the fortress and Galleria Continua, the contemporary art museum.

Day Trips

Having a car or driver will give you access to other local gems in the area. Here are a few that should be on everyone's Tuscan bucket list:

Siena: Gorgeous Siena is, in my opinion, the most beautiful “city” of central Toscana. A small but (for some) better version of Firenze.

Volterra: Just the winding, picturesque drive up to Volterra should be enough to justify a visit to this unique gem.

Cortona: Close to the Umbrian border, in the province of Arezzo lies Cortona, one of the most charming towns in Toscana. It overlooks the Lago Trasimeno and is where the film Under The Tuscan Sun (with Diane Liane and Raoul Bova) was filmed.

Monteriggioni: If you are feeling touristy, stop here halfway through your drive on the superstrada between San Gimignano and Siena. It is the Tuscan version of a Game of Thrones town.

• Osteria del Carcere: a true taste of San Gimignano. Tell Elena and Riva that I sent you, sit back and enjoy a place which takes pride in shooing away tourists that ask for pizza and pasta. Make sure to accompany your dinner with a bottle of the finest white Vernaccia di San Gimignano.

• La Mandragola: Run by Nicola and his son, La Mandragola serves up the finest local food on a terrace in the middle of town.

• Ristorante Fuoriluogo: A nice restaurant, not afraid of experimenting with the finer side of cuisine, where the local San Gimignanesi routinely flock to.

• Fattoria Poggio Alloro: It is a short drive toward Ulignano to find this old school agriturismo where you will eat only produce grown directly on their farm!

• Enjoy: Toscana is not known for its pizza but if you are craving it, book a table here. Arrive before sunset for a magnificent view while you sip on an Aperol Spritz. My wife and I held the welcome drink for our wedding here.

• Gelateria Dondoli: Of course, any stop in SG must include stopping by the two time Gelato World Cup winner (yes, it's a real thing) in Piazza della Cisterna. (BE CAREFUL: it's NOT the one across the square, which has a big wooden sign saying THE BEST ICE CREAM IN THE WORLD, that one instead is the great great Nonna of all tourist traps!)

• Il Criollo: The local bakery that made my wife and I a divine cheesecake with pistachio crumble for our wedding. Il Criollo is an elite, cosmopolitan bakery that just happens to be located in the heart of the Tuscan countryside. A perfect place for colazione with spremuta e cornetto or for a mid-afternoon indulgence.

• If you like the Vernaccia wine, stop by Enoteca Antica Latteria, say hi to Maurizio and Tiziana and buy a bottle (or case) of Vernaccia.