Anxieties will fade away as you drive through Tuscany, your eyes sweeping over the emerald rolling hills, covered with fields of olive groves and vineyards. You can almost taste the fine olive oil and smell the high-quality wine as you make your way to San Gimignano: Tuscany’s town of fine towers.

After a half hour of driving from Gambassi Terme, our GPS told us we had reached our destination. Good thing I had seen pictures of San Gimignano’s towers because we were in the wrong town. Oops!

Small Town Travel Tip: always put the postal code into your GPS to find your destination. The foreign street names are killer to enter correctly.

Let’s try this again… a different address entered in the GPS and another half hour drive through Tuscany and we arrived at San Gimignano. There are paid parking lots outside the town walls. Save yourself the trouble and park in the first lot where you can find a space. We continued to drive and ended up inside the town on streets too narrow for a car to fit. It was a challenge to get turned around and back to where we were supposed to be.

History of San Gimignano

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Stepping onto the streets of San Gimignano is like stepping into a picture-perfect medieval postcard. A UNESCO World Heritage Site since 1990, the town is famous for its vast number of towers that reach above the skyline. As many as 72 towers hovered over the town in its heyday with 13 towers remaining today. Standing at 54 metres, Torre Grossa is the tallest of the towers. The tower has been unchanged since its construction in 1311.

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San Gimignano was settled during the 3^rd century BC. By the 10^th century AD, San Gimignano had become a town. The hilltop location was a strategic choice for protection. With a population of 13,000, San Gimignano had become a thriving stop for trade and pilgrims travelling to Rome. The plague hit in 1348 and decimated two-thirds of the population. Hence, the beginning of the decline of San Gimignano.

The town was not going to give in to demise; however, and during the 18^th century, things began to turn around for San Gimignano. Agriculture increased the population and cultural tourism began to bring visitors to the town of towers once again. As a result, millions of people a year now visit San Gimignano, so it is no longer a sleepy destination. The streets are busy and there are a lot of tourists.

8 Things to Do in San Gimignano

1. Walk Along the City Walls

Not only the town is stunning with its medieval architecture, but the views of Tuscany are outstanding. Make sure to make your way to the top of the town where the Vernaccia Wine Museum is located, stand on the walls of this ancient town and enjoy the view. Take lots of pictures!

2. Wander the Side Streets

Get off the main streets laden with tourists and walk down the medieval paths where there is literally nobody but you. It is easy to take yourself back to medieval times away from the hustle and bustle of the town. If you don’t like getting “lost”, take a map from tourist information so you can find your way around the town.

3. Stroll Down to the Medieval Fountain

It is a long walk down so remember it is also a long walk up! Consequently, there are little or no tourists at this contemplative spot. Le fonti medievali is where the medieval people drew water and washed their clothes. The fountains date to the 14th century and boast Roman arches.

4. Sant’Agostino Church

Chiesa Sant’Agostino is located at the northern tip of the village. The church is in a quieter section of town. Construction of the ancient structure began in 1280. The frescos in this church are exceptional and depict life in the town during medieval times. Entrance into Sant’Agostino is free.

5. Piazza Sant’Agostino

If you want to escape the busier streets, take your time and enjoy Piazza Sant’Agostino. This quiet plaza is a place where you can relax or grab a bite to eat. It is a good place to stop after visiting Chiesa Sant’Agostino.

6. Visit the Duomo

The Duomo is in, you guessed it, Duomo Square (Piazza Duomo). The Duomo is both a temple of faith and art. The inside is fully-frescoed and has never required restoration. The colours you see are the original ones painted in the 1300’s. There is a charge to enter the Duomo.

7. View the Towers in Piazza Duomo

This square is a popular must-see attraction. Here you can view towers from ground level. There are also places to stop and eat, or just hang out and people watch.

8. Visit the Vernaccia Wine Museum

Here is where you will also see the most stunning views of the countryside. Visit the museum for free. Before you leave, sip a glass of Vernaccia di San Gimignano, the white wine of Tuscany. Tastings with expert sommeliers are available for a cost.

Find and book Tuscany tours and activities on Viator.com. Book ahead to save time and money!

Where to Eat in San Gimignano

We opted to have lunch at Locanda di Sant’Agostino, located in the Piazza Sant’Agostino. This restaurant has been family-run for 22 years and offers a delightful, covered patio on the square. It was quiet since it is not a touristy area of the town. The food is purchased locally and is preferably organic. It is a little expensive and the portions are not large but it is worth it for handmade pasta. The gnocchi and boar’s ribs were cooked perfectly, complimented by a delicate sauce. “Everything you see I owe to pasta.” – Sophia Loren

Tuscany’s Town of Fine Towers

San Gimignano is beautifully preserved considering it was bombed during World War II. Visiting medieval towns will get you hooked on experiencing more of these historical attractions. San Gimignano was a day trip for us but it is easily a destination worthy of more time. There are enticements for everyone in this famous medieval town from restaurants to shopping to enchanting bygone charms. Don’t miss this incredible travel destination and all it has to offer.

All pictures in this post are taken by Charlotte, yours truly, as always, unless otherwise stated.