Tuscan Roadtrip: San Gimignano - Thyme for Motherhood

The pint-sized medieval hilltop town of San Gimignano is the perfect introduction to all the beauty of Tuscany.

Most people make a beeline to see the famous Leaning Tower of Pisa, but we went to San Gimignano instead. This won’t be our last trip to Pisa Airport as it is a gateway to other destinations such as Cinque Terre. We’ll be sure to put Torre di Pisa on the list next time. First stop on our Tuscan road trip: San Gimignano!

Things to Do in San Gimignano

UNESCO World Heritage Site since 1990, San Gimignano or “Town of Five Towers,” is a picturesque walled medieval hill town. A wonderfully preserved town surrounded by bucolic countryside, San Gimignano is the perfect introduction to all the beauty, architecture, and rich history of Tuscany. Due to its compact size, San Gimignano is perfect as a day trip. You can easily spend the day exploring narrow alleyways, marvel at the stunning buildings, and enjoy the views.

Piazza del Duomo

As you stroll through the main thoroughfare in San Gimignano, be sure to visit some artisan shops. There are plenty of cafes, delis, and boutiques to spend your hard earned pound (or dollar). You’ll eventually find yourself at Piazza del Duomo and the town’s Romanesque cathedral. Inside the Duomo, there are fourteen travertine stone columns with archways in traditional Tuscan striped motif. Adorning the walls is a series of Renaissance frescoes depicting stories from the Bible with hues of blue across the ceiling.

Torre Grossa

Originally built in the 12th and 13th centuries as defensive structures, there are some 70+ towers in San Gimignano hence the nickname “Medieval Manhattan.” Today there are 14 remaining including the Devil’s Tower, Torre Grossa and Rognosa. The tallest and most famous among them is Torre Grossa with some 200 steps to reach the top.

Piazza della Cisterna

Another historic landmark in San Gimignano with its distinctive triangular shape, owing its name from the main public cistern. Known as the heart of San Gimignano, Piazza della Cisterna hosts regular markets, events and festivals. Surrounding the square are numerous wine bars and home of the famous Gelateria Dondoli. Vinaio di San Gimignano is a great spot to pick up local Italian sandwiches.

View Points

Meandering through the narrow alleyways and the mediaeval wall, you are bound to find a lovely view point overlooking the gorgeous countryside. Find a cute cafe and enjoy an espresso and biscotti with a view of the Tuscan countryside.

Sadly we had to be one our way to Montepulciano, our base for the next three nights. Whilst our stop in San Gimignano was short and sweet, it was worth the detour if only to marvel at the architectural wonder of “medieval Manhattan.”