GemmaSan Gimignano. The medieval jewel of Tuscany. The town of towers. A place where history whispers from every cobblestone and gelato might just change your life. If you’re planning a day trip here, you’re in for a mix of awe-inspiring architecture, charming streets, and yes, some serious food indulgence. From my own personal experience, a day in San Gimignano is like stepping into a living postcard—you might find yourself wandering around, camera in hand, smiling like a tourist cliché, and loving every second of it.
Whether you’re a history buff, a foodie, or just someone who loves a good view, this guide will take you through 10 things you absolutely must do in San Gimignano. Let’s dive in.
1. Climb the Torre Grossa
If you’re wondering which tower to climb among the 14 that still stand, Torre Grossa is your answer. At 54 meters, it’s the tallest tower in San Gimignano, and climbing it gives you a 360-degree view of the town and the rolling Tuscan countryside beyond.
From my own personal experience, the climb is a workout. But trust me, the view is worth it. You’ll see the red-tiled roofs, the surrounding vineyards, and on a clear day, the countryside stretches as far as the eye can see. Take your time at the top, soak it all in, and maybe try to spot where your lunch will be later.
Pro tip: Go early in the morning to avoid the crowds and capture the soft, golden light over the towers.
2. Wander the Piazza della Cisterna
The heart of San Gimignano beats strongest in Piazza della Cisterna. This triangular square is lined with medieval buildings, boutique shops, and cafes. It’s perfect for people-watching and just soaking up the ambiance.
Make sure to check out the well in the middle—the Cisterna—dating back to the 13th century. It’s not just decorative; it was essential for providing water to the townspeople. If the square looks lively, it’s because locals and tourists mingle here constantly, creating a vibrant, almost cinematic atmosphere.
Tip: Stop for a coffee or gelato at one of the cafes surrounding the square. Watching the world go by from a shaded terrace is one of those simple pleasures that makes a day in San Gimignano feel timeless.
3. Taste the World-Famous Gelato at Gelateria Dondoli
Gelato isn’t just a treat in San Gimignano—it’s practically a religion. And if you want the best, Gelateria Dondoli is where you need to go. This gelateria has won multiple awards, and from my own personal experience, the flavors are mind-blowing.
Try the saffron or the Vernaccia wine gelato—unique flavors you won’t find anywhere else. The lines might be long, but patience is rewarded with creamy, rich, perfectly balanced gelato that melts in your mouth.
Pro tip: If you’re indecisive (and who isn’t when faced with dozens of options), go for the “tasting cup” and sample three flavors at once. Your taste buds will thank you.
4. Explore the Collegiata di Santa Maria Assunta
This 12th-century church is not just an architectural marvel—it’s a treasure trove of medieval art. Its frescoes depict biblical scenes in a way that’s both detailed and surprisingly expressive.
Walking inside, you’ll notice the quiet, almost reverent atmosphere. Take your time to study the frescoes and notice the attention to detail in each figure. From my overall experience, visiting this church gives you a sense of how deeply history and religion were intertwined in the daily lives of San Gimignano’s citizens.
Tip: Don’t rush through. Sometimes the best experiences are the quiet ones, standing in a centuries-old church and imagining what life was like back then.
5. Stroll Along Via San Giovanni
This street is the main artery of the old town, and walking here is like traveling back in time. Lined with shops selling everything from leather goods to local wines, Via San Giovanni is perfect for picking up souvenirs or just window-shopping.
Pay attention to the small details—the carved stone facades, the wooden shutters, and the hidden courtyards. From my personal experience, it’s these little streets that capture the essence of San Gimignano more than the major attractions ever could.
Tip: Don’t be afraid to explore side streets. Some of the best shops and quiet spots are tucked away from the main thoroughfare.
6. Visit the Museo Civico
If you love history, the Museo Civico is a must-see. Located in the Palazzo Comunale, the museum houses a fascinating collection of medieval art, manuscripts, and historical artifacts. You’ll get a deeper understanding of San Gimignano’s rise as a wealthy medieval town.
Highlights include original frescoes and ancient documents that detail the town’s political and economic history. It’s surprisingly engaging, especially if you take the time to read the descriptions.
Tip: Combine your museum visit with climbing Torre Grossa—it’s in the same building, so you can admire art and then take in the panoramic view in one trip.
7. Sip Vernaccia di San Gimignano
No visit to San Gimignano is complete without tasting the local wine, Vernaccia di San Gimignano. This white wine is crisp, fresh, and perfect for sipping on a sunny afternoon.
There are several wine shops and tasting rooms in the town, many of which offer tastings at a very reasonable price. From my own personal experience, even if you’re not a wine connoisseur, a glass of Vernaccia enhances the charm of your day, especially when paired with some local cheese or a slice of pecorino.
Tip: Ask the staff for pairing suggestions. They’re usually happy to share their favorite combinations with you.
8. Discover Hidden Courtyards and Gardens
San Gimignano isn’t just about towers and squares—it has charming courtyards and gardens tucked behind its historic walls. Wander away from the main streets, and you’ll find peaceful spots that feel like secret escapes.
These hidden spaces often feature old stone fountains, flowering plants, and benches where you can take a quiet break. From my overall experience, finding one of these quiet corners makes you appreciate the town even more—it’s like discovering a private side of history.
Tip: Keep your eyes open for small gates or archways. They often lead to these magical hidden gems.
9. Shop for Local Products
If you’re looking to take a piece of San Gimignano home, you’ll be spoiled for choice. Leather goods, handmade ceramics, saffron, honey, and local wines make excellent souvenirs.
From my own personal experience, the best finds are often from small shops tucked away in the side streets rather than the ones in the main squares. You’ll also have a more personal interaction with shopkeepers, who are often happy to tell you the story behind their products.
Tip: Don’t forget to try some local sweets. Panforte and ricciarelli are traditional Tuscan treats that pair beautifully with coffee or wine.
10. End Your Day with a Sunset View
As your day in San Gimignano winds down, find a spot to watch the sunset. The town’s elevated position provides stunning views over the surrounding Tuscan hills, and the light at sunset is simply magical.
From my overall experience, this is the perfect way to end your visit. The sky turns shades of pink, orange, and purple, the towers cast long shadows, and the streets gradually quiet down. It’s a moment that makes you pause, breathe, and just appreciate the beauty of where you are.
Tip: Bring a camera, but also take a few minutes to enjoy it without any filters. Sometimes, the real view is better than any photo.
San Gimignano is more than just a day trip—it’s an experience that stays with you. From wandering medieval streets and climbing towers to tasting world-class gelato and sipping local wine, every moment in this town feels special.
Planning your visit carefully allows you to see the must-see sights, explore hidden corners, and truly connect with the charm and history that make San Gimignano one of Tuscany’s most beloved towns. Whether you’re traveling solo, with friends, or with family, these 10 activities ensure a full, memorable, and delightful day.
From my own personal experience, the best advice I can give is to take it slow. Don’t rush. Let the town reveal itself to you, one cobblestone street, one hidden courtyard, and one gelato at a time. San Gimignano is a place that rewards curiosity, patience, and a willingness to get lost in its charm.
So pack your walking shoes, bring your appetite, and prepare for a day that you’ll remember long after you leave.
I’m Gemma, a passionate lifestyle blogger sharing my creative world with you. Gemitaliano.com is my little corner of the internet, glad you’re here.