San Gimignano sits high on a hilltop about 24 miles northwest of Siena surrounded by soaring medieval towers. The walls are tall, the streets narrow and very typical of Tuscan hill towns. It was first settled in the 3rd century BC by the Etruscans and the buildings and city plan were based around 2 major streets with 4 main piazzas. Today 14 towers still remain but there were more than 70 at one time. These towers were constructed partly for defensive purposes and like in other towns we have visited were used for pouring boiling oil on attacking enemies. Ouch! They were very convenient, of course, for spotting marauders and were virtually impregnable. However, ego most likely played a role to own the highest tower and were a symbol of a family’s economic power in the city. The towers are visible from great distances, thus the name “Manhattan of Tuscany”.


The town is a very well preserved medieval town in close proximity to both Florence and Siena. Like Siena it was also devastated by the Black death of 1348 and then fell under Florentine control.  San Gimignano is a walled city and very touristry so expect lots of crowds.  The center is closed to traffic so you must park in an outer lot and walk in. Again a steep hilly town so wear comfy shoes!


The town’s main 12th century church is not an official Duomo because there is no bishop there. The facade is Romanesque and is filled with important frescoes covering the interior by Bartolo di Fredi and Ghirlandaio as well as two famous wooden statues by Jacopo Della Quercia.



Don’t miss the gelato at Gelateria Dondoli it is totally worth the wait!! They say the best in the world! You decide- we agreed! Enjoy your gelato in the piazza in the heart of San Gimignano.  There were several bands there on the evening we visited entertaining the crowds!


The evening is lovely when it gets a little quieter and be sure to enjoy the local white wine called Venaccia di San Gimignano produced here since 1276 and was mentioned by Dante in his ‘Divine Comedy’. It has a distinctive dry and sharp taste. Vernaccia di San Gimignano, normal and riserva is made from 85%-100% of Vernaccia di San Gimignano grapes and traditionally produced in the territory surrounding San Gimignano in the countryside of Siena in the Val D’Orcia.


For a lovely view walk up to Rocca di Montestaffoli  which was a 14th century fortress and is now a public garden with amazing views at the highest point of San Gimignano. From here you can see the towers and the entire countryside. In summer there is an outdoor cinema!


Make sure to also follow the signs that say “Vista Panoramica” that loops around the city for spectacular views all around the Tuscan landscape.


If you missed any of the other blogs on Tuscany here is a link to get you started: Siena