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12 Essential Things to Do in San Gimignano, Italy

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I recently spent several days in Tuscany, and returning to this region is always a gem. I’ve spent plenty of time here, and it never gets old. These are my favorite things to do in San Gimignano to make the most of your trip.

Exploring the streets of San Gimignano today feels like stepping back in time, as the town has remained largely unchanged since the Middle Ages. The city’s architecture, layout, and atmosphere are beautifully preserved, offering a rare glimpse into the past and allowing visitors to immerse themselves in the rich history of this enchanting Tuscan gem.

What is San Gimignano Known for?

Twilight at Piazza della Cisterna, San Gimignano
Kyle Kroeger / ViaTravelers

San Gimignano, a charming medieval town nestled in the heart of Tuscany, is renowned for its rich history and unique architectural features. During the Middle Ages, San Gimignano flourished due to its strategic location along the Via Francigena, a major pilgrimage route, and its proximity to another important route leading to the harbor of Pisa.

Pisa, a maritime republic at the time, was one of the most significant ports in the Mediterranean region, and San Gimignano benefited greatly from its trade connections.

The town is famous not only for its stunning tower houses, which have earned it the nickname “Medieval Manhattan,” but also for its exceptional local products and handicrafts. The golden era of San Gimignano’s prosperity spanned from the 11th to the 14th century, but the town’s fortunes dramatically turned in 1348 when the Black Plague struck.

A significant portion of the population perished, and just three years later, Florence conquered San Gimignano, stripping the town of its independence and marking the beginning of a steep decline.

1. Visit the Piazza del Duomo

Christmas tree lights up medieval San Gimignano square
Kyle Kroeger / ViaTravelers

At the heart of the medieval tapestry that is San Gimignano is the Piazza del Duomo – a captivating tableau of historical and architectural grandeur. Enveloped by the towering façades of centuries-old structures, it’s a testament to the wealth and power of this once-flourishing city-state. It’s a great place to start your adventure or find a place to eat.

But it’s also a great photo op and an essential stop for history nerds. The Duomo (or Cathedral) is a real treat, showcasing Italian Medieval architecture and beautifully frescoed walls and brickwork. While the building is nearly 900 years old, most of the art is from the Renaissance. Some of the paintings are wonderfully vivid, making it a fantastic thing to do on a day trip.

2. Visit the Palazzo Comunale, Pinacoteca, and Torre Grossa

Twilight over cobblestoned San Gimignano, medieval towers rising against the Italian sky
Kyle Kroeger / ViaTravelers

The Palazzo Comunale (or Municipal Palace) is another key feature of Piazza del Duomo and San Gimignano’s skyline. Within this medieval palace, the revered Pinacoteca Gallery hosts a collection of masterpieces and a considerable collection of Italian Renaissance artwork.

The palace is also adjoined by the stately Torre Grossa (the Great Tower), which commands the skyline and can be toured. At over 177 feet or around 54 meters, it’s the tallest tower in the city and one of the best-known medieval towers in Tuscany. Reaching the top reveals a breathtaking panorama of the city and surrounding countryside.

See Related: UNESCO World Heritage Sites in Europe You’ll Want to Visit

3. Visit the Torre Chigi

Christmas tree lighting at dusk in San Gimignano, Italy
Kyle Kroeger / ViaTravelers

From the tallest tower to one of the shortest, the rectangular Torre Chigi can also be found on Piazza del Duomo. You can easily forgive its relative stumpiness compared to the city’s 13 other towers, mostly because it’s arguably the most beautiful of all San Gimignano’s towers.

Made from different colored stones, this 13th-century tower was built as a private castle and essentially still is, as people do indeed live there. While tours are all but impossible, it’s a wonderful photo op. Alright, let’s move on to more fortifications!

4. Porta delle Fonti

View of Porta delle Fonti in San Gimignano
gaspa / Wikimedia Commons, CC BY 2.0

History buffs, keep walking a little further off the beaten path and head towards one of the gates in San Gimignano’s city walls — the Porta delle Fonti. This relatively secluded spot is in good condition and an interesting example of medieval architecture.

The outside of the gate features a Sienese-style arch, typical of many town gates in Tuscany, but inside, it features a taller, rounded arch. Once you exit the gate, you’ll wander down a steep hill to our next attraction.

5. Visit the Fonti Medievali: Wondrous Waters Enveloped by Nature’s Embrace

The wall of Fonti Medievali in San Gimignano
gaspa / Wikimedia Commons, CC BY-SA 2.0

History nerds will also get a kick out of this next one, the Fonti Medievali, a medieval fountain, and a legit hidden gem. Nestled in a blanket of greenery, bearing centuries of scars, tranquility echoes through the weathered stone wells. This secluded sanctuary invites you to indulge in a restorative pause on your journey through San Gimignano’s historical marvels.

See Related: Most Beautiful Towns in Europe to Visit

6. Visit the Parco della Rocca

Door at Parco della Rocca in San Gimignano
Sonja / Adobe Stock

Next up is Parco della Rocca, a pretty unique spin on a public park, considering it’s located within the grounds of a ruined medieval fortress – the Rocca of Montestaffoli. Passing through its crumbling stone gates, each step along the cobblestone pathways offers sweeping views of Tuscany’s hills and San Gimignano.

The remnants of the once-formidable fortress blend seamlessly with the natural beauty, providing a beautiful tableau for photographers. Whether you’re a history buff picking apart the fortress ruins or picnicking in the shade of olive groves, this park is one of a kind and the perfect place to appreciate the allure of San Gimignano.

7. Visit the SanGimignano1300: An Unforgettable Journey Through Time

San Gimignano 1300 museum display
JESUS SOLERO / TripAdvisor

Historically, San Gimignano was a medieval powerhouse; you can learn all about it at San Gimignano 1300. This marvelous multimedia medieval museum presents a window into the past, showing what life was like in San Gimignano in 1300.

It’s particularly well known for its famous miniature ceramic recreation of San Gimignano. I love a miniature village, and this one is simply exceptional, providing a glimpse of life as a tradesman, merchant, and nobility in beautiful detail. This is another top stop for the historically inclined and an ideal activity for the bambinos.

8. Piazza della Cisterna

Twilight at Piazza della Cisterna, San Gimignano
Kyle Kroeger / ViaTravelers

Okay, we’ve gone far too long without mentioning another tower. So let’s go to the Piazza della Cisterna and see if we can find a bite while we’re at it. With terracotta tiles underfoot, this gently sloping square takes its name from the cistern where locals could draw water.

It’s also surrounded by five of the city’s 14 towers and beautiful architecture from the Middle Ages to the 18th century. If you need some retail therapy, you can find a few boutiques and stalls in and around the square, not to mention places to grab a hot lunch, espresso, or gelato. Once you’re fueled up, it’s time to move on to the next tower!

9. Torre dei Cugnanesi

Torre dei Cugnanesi structure  and skyline in Torre dei Cugnanesi, San Gimignano, Italy
H-AB Photography / Adobe Stock

The Torre dei Cugnanesi on the Piazza della Cisterna is another one of the city’s tallest towers. It starkly contrasts some of the others on this list, somewhat menacing in its height and simplicity. Almost resembling a square stone smokestack, this 13th-century tower is another historic part of the city’s defensive network of walls, gates, and other towers.

See Related: ​​Best Museums in Europe to Visit

10. Torre and Casa Campatelli

Torre and Casa Campatelli in San Gimignano
Marco Giovannelli / TripAdvisor

Just take a quick walk from Torre dei Cugnanesi, and you’ll find yourself at the Torre and Casa Campatelli. The Torre Campatelli is one of the widest towers in town, built in the 12th Century. Following a recent restoration, you can actually tour this tower, and you can also tour the 18th-century family home of the entrepreneurial Campatelli family, who gave this squat tower its current name.

Housing a wealth of familial legacies within its robust, frescoed walls, this palazzo-house museum presents a fusion of art, culture, and history, filled with stunning 19th and 20th-century art and furnishings.

11. Try World Champion Gelato at Gelateria Dondoli

Authentic Italian gelato selection at World Famous Gelateria Dondoli in San Gimignano
Kyle Kroeger / ViaTravelers

In recent years, San Gimignano has gained recognition for yet another delightful treat – gelato. Gelateria Dondoli, located in the town’s main square, has twice been awarded the prestigious title of “Best Gelato in the World,” drawing food enthusiasts from far and wide to savor its creamy delights.

Enjoying Gelateria Dondoli gelato at night in San Gimignano Piazza
Kyle Kroeger / ViaTravelers

It’s a must-visit and very reasonably priced. Just get there early so you can avoid the long lines.

12. Shop for Local Artisanal Products and Wine

Wine Grapes Maturing in a Glass Box
Kyle Kroeger / ViaTravelers

San Gimignano is celebrated for its fine ceramics, high-quality leather goods, and the precious saffron, once used as a valuable pigment during the Middle Ages before its culinary potential was discovered. Today, saffron is a prized ingredient, often adoring dishes like risotto. Perhaps one of San Gimignano’s most notable claims of fame is its white wine, Vernaccia di San Gimignano.

This wine, made from the ancient Vernaccia grape variety, believed to be the ancestor of Pinot Gris, was the first white wine in Italy to receive the coveted DOCG (Denominazione di Origine Controllata e Garantita) status. The production of Vernaccia wine is strictly limited to the hills surrounding the town, ensuring its authenticity and quality.

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