Travelling from Florence, you can take a bus from SITA bus station and change at Poggibonsi to reach San Gimignano. The bus ride takes a total of around 1.5 hours. If you are covering Siena and San Gimignano on the same day, then take a bus from Siena, here again, you will have to change the bus at Poggibonsi. If you wish to skip the bus ride, then rent a car. From the bus station, it is a small walk to the beautifully preserved walled medieval hill town of Tuscany—San Gimignano. People often refer to it as the ‘Manhattan of Tuscany’ owing to its numerous medieval towers and not because it has skyscrapers like the real Manhattan. It is a lively hill town village with beautiful medieval towers and structures amidst vineyards growing in all directions.

A small walk through the beautiful narrow alleys will lead you to Piazza della Cisterna, which is the most beautiful and frequently visited ‘triangular shaped square’ in San Gimignano. The piazza gets its name from the underground cistern, which is postcard worthy, and you might have seen it in many of the artworks, postcards and framed photos. There is a gelateria near the cistern by the name Gelateria Dondoli, which you will never miss due to the long queues and crowd outside it. ‘Great gelato’, ‘the world’s best gelateria, ‘the best in Italy’, ‘visited by celebrities’ are only some of the many things that you will hear about this gelateria. All said and done, you cannot proceed until you have at least one gelato here. Now that you have enjoyed the world’s best gelato, walk towards the trapezoid-shaped Piazza del Duomo that will be crowded by tourists during the daytime. Once inside, you will time travel to the medieval era!

While exploring the beautiful medieval hill town further, shop for souvenirs, locally made white wine, photos and postcards. Foto Fontanelli is a photo-shop with exquisite collections of Tuscany as well as the entire Italy. You can find photos and postcards in various sizes, which will be an excellent gift option, and something that you can put up on the wall of your home. Keep moving uphill until you reach the castle Rocca di Montestaffoli, which was built in 1353. The castle is not as impressive as the breathtaking views of Tuscany vineyards and the town of San Gimignano that you get from here.

San Gimignano is abuzz with tourists during the day while nights are quieter. If you want to enjoy the quietude of this beautiful medieval town at night then overnight stay is required and for this you will have to make prior arrangements as options to stay in San Gimignano are relatively limited.