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The Ultimate Travel Guide to San Gimignano, Italy

San Gimignano is one of those places that feels like it was made for wandering. Perched on a hill in the heart of Tuscany, this walled medieval town is famous for its skyline of stone towers—and yeah, it really does look like a fairytale. I went as a day trip and honestly, by the time I was leaving, I was already thinking about when I could come back. They call it “The Manhattan of the Middle Ages,” and once you see those towers, you’ll get why. It’s small, super walkable, and packed with charm around every corner. Whether you’re into history, scenic views, delicious food, or just want to soak up that dreamy Tuscan vibe, San Gimignano has a way of pulling you in.


Getting to San Gimignano, Italy

San Gimignano doesn’t have a train station, but it’s easy to reach with a little planning.


By Car:

Driving is by far the easiest way to get there—and the most scenic. I rented a car from Florence and the drive through the Tuscan countryside took just over an hour. I booked through SIXT, and they made the whole process super smooth, from pickup to drop-off. Of course, you can go with any rental company you prefer—just make sure to book in advance, especially in high season. You’ll park outside the city walls—Parcheggio Montemaggio is a great option and only a short walk into the center.




Tip: Download your offline map in advance, especially if you're driving through rural areas—cell service can be spotty in the countryside!


By Bus:

If you’re not driving, taking the bus is still a great and budget-friendly way to reach San Gimignano. From Florence, you’ll take a bus to Poggibonsi, and then transfer to a local bus that takes you directly into San Gimignano. The whole trip takes about 1.5 to 2 hours, and the final stop drops you off just outside the city gate—super convenient. For planning and real-time updates, I recommend using the official Busitalia apps to check routes, schedules, and ticket availability. You can also use the Omio app—which I’ve personally used for train travel in Italy. It also works really well for booking buses and comparing schedules between different carriers.







Tip: Try to leave Florence early so you can enjoy a full day in San Gimignano without feeling rushed.



Things to Do in San Gimignano, Italy

This town might be small, but it’s full of character and history. Whether you’re into panoramic views, quiet little piazzas, or old churches with a story to tell, here’s everything you’ll want to see while you’re in San Gimignano:


Torre Grossa

If you’re only going to climb one thing while you’re in San Gimignano, let it be this. It’s the tallest tower in town and the only one open to the public for climbing. I’ll be honest—the staircase is steep and narrow in parts, but once you get to the top, it’s so worth it. You’re rewarded with this incredible view of the town’s rooftops, the surrounding countryside, and those iconic rolling Tuscan hills that go on forever. There’s something special about seeing San Gimignano from above—it gives you a whole new appreciation for how unique and well-preserved it is. And since the town isn’t too big, the climb doesn’t take long. Just make sure to wear comfy shoes and bring your camera—it’s a view you’ll want to remember.




Piazza della Cisterna

When I visited, it was drizzling, and honestly? That made it even better. The rain gave the stone buildings this soft glow, the square was quieter than usual, and it felt like I had a little moment of calm right in the middle of town. I grabbed a cone from the famous Gelateria Dondoli (yes, even in the rain—worth it), found a dry spot under an archway, and just watched people pass by with umbrellas and warm drinks in hand. Even with the weather, the square had this cozy, storybook feel. The medieval buildings, the little artisan shops, the sound of footsteps on wet cobblestone—it all just added to the charm.



Duomo di Santa Maria Assunta

From the outside, it’s easy to overlook—it’s simple and blends right into the town’s medieval vibe. But the moment you walk inside, it’s a whole other world. The walls are completely covered in frescoes that bring scenes from the Old and New Testaments to life. Every inch tells a story, and the colors and detail are seriously stunning. Even if you're not big on religious art, there’s something about the atmosphere that pulls you in. I found myself just standing there, slowly looking around, trying to take it all in. It’s peaceful, a little overwhelming in the best way, and definitely one of those “wow” moments in San Gimignano.






Rocca di Montestaffoli

This old fortress might mostly be ruins now, but the walk up is totally worth it. Even on a rainy day, the views over the Tuscan countryside were beautiful—misty hills, quiet olive groves, and that peaceful stillness that comes with gray skies. It wasn’t crowded at all when I went, which made it feel like a little hidden escape from the busy town below. The mix of old stone walls and open skies gives it this calm, grounded energy. Definitely a spot to take your time with.


SanGimignano1300 Museum

This spot totally surprised me. It’s a detailed ceramic model of what San Gimignano looked like back in the year 1300, and it’s way more impressive than it sounds. The craftsmanship is incredible—every little street, tower, and building is carefully recreated. It gives you such a cool perspective on how the town was laid out and how much of it has been preserved. It’s a quick stop, but a really interesting one—especially if you’re into history or love seeing how places looked centuries ago.



Fonti Medievali

Tucked just outside the main part of town, these medieval stone fountains were once where locals came to wash clothes and collect water. Standing there, it’s easy to imagine what daily life looked like centuries ago. It’s a quiet, peaceful spot surrounded by greenery and stone—easy to miss if you’re not looking for it, but worth the detour. There’s something really grounding about being in a place that’s been part of everyday life for so long.


Historic Centre of San Gimignano

You’ll find yourself walking through the historic center all day without even trying. It’s a UNESCO World Heritage Site, and once you’re there, it’s easy to see why. The tall stone towers, narrow cobblestone lanes, and open piazzas feel like stepping straight into another time. Every corner has something to look at—old archways, hanging laundry, little shops tucked into centuries-old buildings. It’s the kind of place where you don’t need a plan—just wander and let the town unfold around you.



Piazza Pecori

Just around the corner from the Duomo, this little piazza is a quiet spot to take a breather. It’s smaller and less crowded than the main squares, which makes it perfect for sitting with a coffee and just enjoying the moment. I stopped here for a quick break, and it felt like such a peaceful pause—no rush, just the sound of footsteps and clinking cups from the nearby café. If you need a moment to reset while exploring, this is a great place to do it.


Porta San Matteo & Porta San Giovanni

These two gates were once the main entrances into San Gimignano, and both are still standing strong. Porta San Giovanni is the busier one—it’s the main entrance most people walk through, lined with shops and a steady flow of visitors. It has that lively, welcome-to-town kind of energy. Porta San Matteo, on the other hand, is quieter and more peaceful. Fewer crowds, slower pace, and a great spot to start or end a more relaxed walk through town. Both gates give you a little glimpse into the town’s past, and each has its own vibe worth experiencing.


Chiesa di Sant'Agostino

This church doesn’t get as much attention as the Duomo, but it’s absolutely worth a visit. The inside is peaceful and beautiful, with soft light, detailed frescoes, and a quiet, reverent feel that makes you want to just sit for a while and take it all in. Right outside, the little square has benches and a calm vibe—perfect for resting your feet or enjoying a snack in between exploring. It’s one of those spots that feels tucked away, even though it’s right there in town.



Piazza Sant'Agostino

Just outside the church, this square has a totally different feel from the busier parts of town. It’s quieter, more local, and has this relaxed charm that makes you want to slow down. Kids play, locals chat, and there's plenty of space to sit and take it all in. It’s a great spot to catch your breath, enjoy the surroundings, and see a different, more laid-back side of San Gimignano—still full of character, just without the crowds.


Torre dei Cugnanesi & Torre dei Becci

These are two of the original medieval towers you’ll probably pass while wandering through town. You can’t climb them, but seeing them up close is still pretty special. The stonework, the height, and just knowing they’ve been standing there for centuries—it really gives you a sense of how impressive San Gimignano must’ve looked back in the day. They’re easy to spot and worth pausing for as you explore—little reminders of the town’s rich, layered history everywhere you turn.



Where to Eat in San Gimignano, Italy

Tuscany never disappoints when it comes to food, and San Gimignano is no exception. Tucked into its winding medieval streets are some truly great spots to eat—whether you’re craving a long, cozy dinner or just something quick and local. Here are a few favorites to check out:


Cum Quibus

This place is small and intimate, with the kind of warm, welcoming vibe that makes you want to linger. The seasonal tasting menu is incredibly thoughtful—each dish feels like a little work of art—and everything pairs beautifully with local wines. It’s one of those meals you remember long after it’s over. If you’re looking for something special, this is it.




Trattoria Chiribiri

This spot is cozy, unpretentious, and full of heart. It feels like the kind of place locals actually eat at, which is always a good sign. The ribollita is rich and comforting, and the pici with wild boar is everything you want from a Tuscan meal—hearty, flavorful, and satisfying. Perfect if you’re craving something warm and traditional.



La Mandragola

Tucked away from the busier streets, this spot has a charming little garden that’s perfect for a relaxed lunch. The menu offers fresh, creative twists on classic Tuscan dishes—still true to tradition but with a bit of flair. It’s peaceful, pretty, and just a really lovely place to take a break and enjoy a good meal.




Osteria delle Catene

This place is as local and no-frills as it gets, and that’s exactly what makes it so good. The pasta is homemade and full of flavor—simple, honest food that hits the spot. It has that warm, homey feel, like you’re having lunch at a friend’s house who just happens to be an amazing cook.




Best Coffee & Gelato in San Gimignano


Gelateria Dondoli

World-famous for a reason. The gelato here is seriously good, and they offer some unique local flavors—like saffron and pine nut—that you won’t find just anywhere. I went with one of their seasonal picks and it did not disappoint. There’s usually a line, but it moves fast, and it’s totally worth the stop.


Caffè Giardino

Just outside the town walls, this cozy café is a great little escape. They serve solid espresso, and the terrace has beautiful views of the surrounding hills. It’s a perfect spot to take a breather away from the busier parts of town.


La Vecchia Lira

It’s a full-on restaurant, but their coffee alone is worth a visit. I grabbed a cappuccino in the morning and sat outside in the piazza—such a peaceful way to ease into the day before diving back into sightseeing.


Where to Stay in San Gimignano, Italy

If you can, stay overnight—it completely changes the vibe once the day-trippers clear out. The streets get quieter, the light softens, and the town feels even more magical.


Hotel L'Antico Pozzo

Elegant, historic, and located right in the heart of San Gimignano. It’s got that classic charm with a touch of luxury—perfect if you want to be surrounded by beauty and history.


Leon Bianco

Sitting right on Piazza della Cisterna, this place is warm, welcoming, and incredibly convenient. You wake up with the town at your doorstep, which is such a nice way to start the day.



Hotel Bel Soggiorno

Technically still in the city center, this one offers spacious rooms and a restaurant serving traditional Tuscan dishes. Cozy and authentic.


Hotel Sovestro

About a mile from the town walls, this hotel has two pools, a small gym, and a great restaurant on-site. It’s a great option if you’re looking for a bit more space and don’t mind a short walk or drive into town.


Best Time to Visit San Gimignano, Italy

I visited San Gimignano in April, and while it was rainy during my trip, it honestly added to the charm. The misty hills, the quiet streets, and the sound of rain on the old stone—it gave everything this calm, moody vibe that made the town feel even more magical. San Gimignano is beautiful year-round, but the experience definitely changes with the seasons: Spring (March–June): Blooming hillsides, mild temps, and fewer crowds. Even with a bit of rain, it’s a lovely time to explore. Summer (July–August): Warm, lively, and full of energy—but also the most crowded. Book ahead and expect the heat.Fall (September–October): That perfect golden light, grape harvest season, and postcard-worthy views everywhere. Winter (December–February): Quiet and peaceful with hardly any tourists around, though some shops and restaurants may close early or take a break for the season.



San Gimignano is proof that small towns can leave the biggest impression. Whether you’re coming for the towers, the wine, the food, or just to feel like you’ve stepped back in time, this place is something special. I loved every minute of wandering those stone streets, even in the rain, and taking in the soft, dreamy views of the Tuscan countryside.

Have you been to San Gimignano? I’d love to hear what spots you loved most!


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