How to Spend a Perfect Day in San Gimignano: A Curated Guide to Tuscany’s Tower Town
From exploring the charming cobbled streets and medieval towers to immersing yourself in the town's rich history, enjoying wine tastings, and indulging in world-famous gelato, these are the best things to do in San Gimignano, Italy
Rising from the Tuscan hills like a medieval mirage, San Gimignano feels impossibly dramatic.
Situated in a patchwork of fields, rolling hills, and vineyards in Tuscany, San Gimignano’s history is long, dating back to the Etruscans & Romans. However, it was during the town's golden age, characterised by intense rivalries between influential families, that an indelible mark was left on the town and the landscape.
Agricultural prosperity in the name of wine and saffron made local families immensely wealthy, and as a symbol of this power, each family strived to build taller and more impressive towers than the others. The result was a sort of “medieval Manhattan”, filled with towers up to 70m tall.
Despite the course of time, wars, plagues, and modernity, many of these towers remain, making San Gimignano one of Tuscany’s most important tourist attractions.
We’re ashamed to admit it, but we knew nothing of San Gimignano before we visited Florence & Tuscany. Nothing. Zilch. This “medieval Manhattan” of outrageous beauty had not so much as made it into our oversaturated Instagram feed.
It was only after we decided to extend a late summer Tuscan stay that we stumbled across it. Scandal.
As it turns out, we’re happy we did. This remarkably preserved UNESCO World Heritage-listed town stole our hearts.
Our time here was short but filled with endless memories of cobbled laneways, stunning views, and delightful food & wine.
San Gimignano offers the perfect day trip from Florence, and its iconic skyline, adorned with ancient towers, is just one part of the appeal. The narrow streets and alleyways hide exceptional restaurants and enotecas serving local delicacies straight from the land. Its piazzas offer the perfect opportunity to sit back and enjoy “la dolce far niente” - the sweetness of doing nothing. The surrounding countryside is home to some of the best wines you’ll ever sample.
But for those willing to stay a little longer, it offers the opportunity to live the Italian dream.
In this guide, you’ll find everything you need to know to enjoy your time in San Gimignano, from the best things to see and do, where to eat, drink and sleep, and how to get there from Florence, Siena and beyond.
Unlike any other village (borgo in Italian) you’ve ever seen, here’s our guide to San Gimignano.
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SAN GIMIGNANO SNAPSHOT
WHERE | San Gimignano, Tuscany
HOW TO GET THERE | Private tour, or car rental. Alternatively, public transport from Florence or Siena
WHAT TO DO | Get lost amongst the cobbled streets, Climb Torre Grosso, History + art at Palazzo Communale
WHERE TO STAY | Hotel La Collegiata, Hotel Leon Bianco, or Hotel San Michele
WHERE TO EAT | Le Vecchie Mura, Gelataria Dondoli & La Vecchia Nicchia di Alessandro Pieragnoli Enoteca
DAY TRIPS | A guided tour of San Gimignano
THE HISTORY OF SAN GIMIGNANO
To truly understand San Gimignano, we feel it’s important to first understand its history.
San Gimignano’s story begins with the Etruscans, who settled the hills long before Rome took an interest.
But it was during the Middle Ages that the town truly flourished, thanks to its strategic position along the Via Francigena, the famed pilgrimage route connecting Canterbury to Rome.
Merchants and travellers passed through in droves, bringing wealth, trade, and the resources to construct both civic buildings and powerful family homes.
By the 13th and 14th centuries, San Gimignano’s rival families were locked in an architectural arms race. Tower houses symbolised wealth and status, and at the peak of this frenzy, the town had more than 70 of them, each taller than the last.
Today, only 14 remain, but they still give San Gimignano its unmistakable, medieval Manhattan skyline.
Plague, political feuds, and the eventual absorption into Florentine rule slowed the town’s fortunes, effectively freezing it in time.
When 19th-century travellers and historians “rediscovered” it, San Gimignano became celebrated as one of Italy’s best-preserved medieval hill towns.
San Gimignano's historical significance and well-preserved medieval architecture led to its recognition as a UNESCO World Heritage Site in 1990.
THINGS TO DO IN SAN GIMIGNANO
GET LOST AMONGST THE COBBLED STREETS OF SAN GIMIGNANO
For long-time readers of The Common Wanderer, you’ll know there’s nothing we love more than getting lost amongst the old laneways and streets of a quaint European town. Such strolls help us discover a place with our own eyes and often lead to the most wonderful outcomes. And this is certainly the case in San Gimignano.
The labyrinth of narrow alleyways, stone arches, and hidden corners, tell a story of San Gimignano’s past.
The towering ochre-coloured buildings and towers, adorned with centuries-old coats of arms and family crests, evoke a sense of history that's almost palpable.
Around every corner, you'll discover inviting cafes, artisan shops, local wine sellers and local trattorias serving up the finest Tuscan dishes. It's a town where getting lost becomes an adventure.
Despite the town’s popularity, as you meander through these charming alleys, you'll often find yourself alone, allowing you to soak in the peaceful ambience and the secrets these streets hold - linen drying in the summer breeze, the sound of fresh pasta being rolled for dinner, the echoes of kids playing hide and seek.
It’s mesmerising.
We suggest starting your stroll along the main entrance to town, the 11th-century Porta San Giovanni, before slowly making your way up via S. Giovanni towards the town centre. From Piazza della Cisterna, the world is your oyster - simply choose a laneway, and follow it to wherever it may go.
Follow your nose and if you stumble across a picture-perfect restaurant or bar, stop, order a local vernaccia wine, and whisper a thank you to us.
WANDERER TIP | Staying in San Gimignano? Book accommodation in the centre of town and enjoy the old town ambience before/after the crowds arrive.
We recommend Fabio Apartments or Hotel Bel Soggiorno
LEARN ABOUT SAN GIMIGNANO’S HISTORY AT PALAZZO COMUNALE
If you’ve visited Florence, Siena, Montepulciano or beyond, you’ll know the region does grand civic architecture like nowhere else. San Gimignano is no exception.
Located on the gorgeous Piazza del Duomo, the grand 13th-century Palazzo Comunale (also known as Palazzo del Pópolo) is characterised by its medieval towers and red-stone facades, which hide grand interiors filled with Medieval and Renaissance frescoes, intricate cloisters, and the tallest tower in San Gimignano, Torre Grosso.
Today, the palazzo houses San Gimignano’s Civic Museum, a compact but fascinating collection that brings the town’s story to life and is absolutely worth a visit if you want to understand San Gimignano beyond its postcard looks.
On the first floor is the Sala del Consiglio (also called Sala Dante), the council chamber where none other than Dante Alighieri addressed the town’s leaders in 1299 as an ambassador of the Guelph League. The room is lined with vivid 13th-century frescoes, including Lippo Memmi’s celebrated “Maestà”, a jewel of Sienese Gothic art depicting the Madonna and Child surrounded by angels.
Continue upstairs to the Camera del Podestà, decorated with a wonderfully restored fresco cycle by Memmo di Filippuccio. These scenes, which show a married couple in bed and in the bath, are unusually intimate (and mildly scandalous) for the early 1300s, illustrating the domestic “pleasures” of married life.
Nearby, the Pinacoteca holds a small but charming selection of Renaissance works by artists such as Filippino Lippi, Pinturicchio, Benozzo Gozzoli, and Taddeo di Bartolo, showcasing various themes such as the Annunciation and the life of St. Gimignano.
Your visit naturally leads to Torre Grossa, the adjacent 54-metre tower, which offers the best panoramic views of the town's iconic towers and the surrounding Tuscan countryside (more on that below).
THE DETAILS
Where | Palazzo Comunale, Piazza del Duomo
Entrance Fee | Civic Museum + Torre Grossa combined ticket: €15 adults / €12 reduced (ages 6–17), Stand-alone museum ticket ~ €9
Opening Hours | April–October: 10:00–19:30 // November–March: 10:00–17:00
(Closed during council events, religious holidays, and select dates in Jan/Mar/Aug/Nov)
CLIMB SAN GIMIGNANO’S FAMOUS TOWERS
Seeing the soaring sentinels that dot San Gimignano’s skyline for the first time can feel a little overwhelming.
As you approach the town, you’ll see a group of red-brick towers reaching toward the sky, seemingly out of nowhere. They look horribly out of place against the backdrop of rolling hills and vineyards, but it’s this juxtaposition that makes San Gimignano’s towers all the more impressive. It’s little wonder, then, that San Gimignano holds UNESCO World Heritage status.
The iconic towers, often referred to as "Medieval Manhattan," were originally built in the 12th and 13th centuries by the town's wealthy families, not only as status symbols but also as defensive structures during times of political unrest in Tuscany.
At the height of San Gimignano's tower-building craze, there were reportedly 72 towers gracing the town's skyline (can you imagine?!), but today, only 14 remain.
The towers, some more than 700 years old, have seen the ebb and flow of history, and from their lofty summits, you can hear the whispers of the centuries - tales of traders, nobles, and everyday folk who walked these streets long ago.
Torre Grosso, the tallest and most impressive tower, sits alongside Palazzo Communale, and is the easiest to visit for day trippers, providing breathtaking panoramic views over the town and the surrounding Tuscan countryside.
As you ascend the 200 or so stairs, you'll wind your way through narrow stone staircases and cool, dimly lit chambers, some of which host exhibitions about the towers and the town's history. From the top, the views are breathtaking - below, town folk and tourists scamper between piazzas and attractions. In the distance, rolling hills dotted with vineyards mark the famous landscape - for photographers like us, it’s the ultimate subject.
Now for the practical information; there’s a fee of €9 which includes entrance to the town hall (Palazzo Communale), Gallery and Tower. We purchased our tickets in advance, which you can do here. It does get very very busy, so we recommend booking ahead to avoid issues.
In summer months, the tower is daily between 10.00 am - 7.30 pm.
Seeing San Gimignano’s skyline for the first time can feel strangely surreal.
As you approach the hill town, a cluster of slender stone towers rises abruptly from the landscape, a vertical forest of medieval ambition breaking through the soft lines of vineyards and rolling Tuscan hills.
This dramatic contrast is exactly why San Gimignano earned its UNESCO World Heritage status.
These towers, often nicknamed Tuscany’s “Medieval Manhattan,” were built in the 12th and 13th centuries by the town’s wealthiest families, part status symbol, part defensive structure during an era where political tensions simmered across the region.
At the height of the tower-building boom, San Gimignano boasted around 72 towers (imagine that skyline!). Today, 14 survive, each more than 700 years old and filled with the memories of merchants, nobles, pilgrims, and everyday townsfolk who once lived beneath their shadow.
The most commanding of them all is Torre Grossa, standing 54 metres high beside the Palazzo Comunale. It’s the easiest tower for visitors to climb, and the most rewarding.
The ascent winds through narrow medieval staircases and shadowy stone chambers (some housing small exhibits about the town).
Eventually, you emerge onto the rooftop terrace, where the views stretch for miles: terracotta rooftops below, the hum of piazzas drifting upward, and those classic Tuscan ridgelines rolling out in every direction. It’s pure magic, especially late afternoon when the light turns that Tuscan version of golden
For photographers, this is the moment. For everyone else, it’s simply unforgettable.
THE DETAILS
Where | Torre Grossa, located in Piazza del Duomo, the heart of San Gimignano
Entrance Fee | Combined Civic Museums + Torre Grossa: €15 adults | €12 (6–17 years), Stand-alone tower ticket is ~ €9–10 (as of 2025)
Opening Hours | 10.00 am - 7.30 pm in summer
WANDERER TIP | You can stay in one of the San Gimignano towers, which is all kinds of awesome. Book your stay at Torre Salvucci Maggiore here
BOOK | Torre Grosso + Duomo ticket
ENJOY A WINE TASTING
One of the simple joys of being in Tuscany, and Italy in general, is that good wine is never far away.
It’s always delicious, always affordable, and somehow always feels appropriate, no matter the time of day. San Gimignano is no exception.
Beyond its skyline of medieval towers, the town is famous for Vernaccia di San Gimignano, a beautifully crisp white wine and Italy’s first-ever DOCG. Cultivated on these hillsides for centuries, Vernaccia is bright, mineral-driven, and exactly what you want on a warm Tuscan afternoon.
If climbing a tower is non-negotiable in San Gimignano, tasting Vernaccia should be too.
Fortunately, you don’t have to look far. The town is filled with wineries, cellar doors, and enoteche where you can sample the local drop, or simply order a glass and sit in the sun contemplating your excellent life choices.
Our favourite spot in town was La Vecchia Nicchia di Alessandro Pieragnoli Enoteca.
The name is a mouthful, but the wines are sublime - an exceptional little find tucked down a cobbled laneway near the edge of the walls. They pour an excellent range of Vernaccia alongside Chianti and Rosato, and their bruschetta is genuinely a work of art.
For a more casual option, La Fiaschetteria di Boboli is a delightful wine-and-deli hybrid offering panini, cheese, charcuterie, and takeaway glasses of wine you can wander with (responsibly, of course).
If you have time to venture beyond the walls, the vineyards surrounding San Gimignano are as beautiful as they are productive — rolling hills, geometric rows of vines, and sweeping views back toward the medieval skyline.
A few standout wineries nearby include::
Fattoria San Donato | A family-run favourite producing Vernaccia, Chianti, olive oil, and saffron. Their vineyard and cellar tours are relaxed and welcoming, and the views back to San Gimignano are spectacular
Poggio Alloro | A working farm and organic winery that nails the classic Tuscan experience. Expect vineyard tours, generous tastings, and a farm-to-table lunch that pairs perfectly with their wines
Tenuta Torciano | Just outside town, this long-standing family winery offers a diverse tasting lineup — from Vernaccia and Chianti to Super Tuscans — often paired with local specialties.
Fontaleoni | Just outside San Gimignano, it offers wonderful tastings in a picture-perfect setting. And if you’re keen to deep-dive into Vernaccia specifically, several dedicated tasting tours operate in the region.
To fully understand and enjoy the local wine scene, we suggest booking a wine-tasting tour at Fontaleoni, a picturesque winery just outside of San Gimignano. Or, if Vernaccia is more your vibe, this tour samples the best in the region.
THE DETAILS
Where | La Vecchia Nicchia di Alessandro Pieragnoli Enoteca
BOOK | This popular, romantic wine-tasting tour
STEP INSIDE DUOMO SAN GIMIGNANO, AND CHIESA DI SANT’AGOSTINO
In the heart of San Gimignano sits the 12th-century Duomo di San Gimignano, a church that looks deceptively plain from the outside.
Step through its doors, though, and you’re met with one of Tuscany’s most extraordinary frescoed interiors, a complete, wall-to-wall cycle of medieval art that feels almost untouched by time.
Also known as the Collegiate Church of Santa Maria Assunta, the Duomo’s interior glows with the rich polychrome decoration typical of the era: deep blue vaulted ceilings, patterned arches, and a striking black-and-white striping reminiscent of Siena’s cathedral.
The walls are entirely covered with frescoes depicting the Old and New Testaments, painted by some of the region’s most celebrated artists.
The standout is the Chapel of Santa Fina, where Domenico Ghirlandaio beautifully illustrates the life of San Gimignano’s beloved saint.
Her tomb carries a poetic inscription honouring her as the town’s “glory, example, and guardian,” guiding visitors to look not for miracles but for meaning in the vivid imagery around them.
At the rear of the church, you’ll also find Taddeo di Bartolo’s Last Judgment — dramatic, finely detailed, and impossible to miss.
A visit to the Duomo is short and sweet (20–30 minutes), but absolutely essential.
CHIESA DI SANT’AGOSTINO
On the quieter northern side of the walled town sits Chiesa di Sant’Agostino, a 13th-century Romanesque beauty that receives only a fraction of the crowds, despite being home to some of San Gimignano’s finest frescoes.
The façade is simple and calm, but the interior is rich with colour and detail. Many frescoes date back to the 14th and 15th centuries and remain surprisingly vivid.
The highlight is the cycle by Benozzo Gozzoli, whose scenes depicting the life of St Augustine in the Chapel of St Jerome are intimate, expressive, and worth the short stroll alone.
Controversial as it may be, we actually preferred Sant’Agostino to the Duomo — but both deserve a spot on your itinerary.
THE DETAILS
Where | Duomo San Gimignano & Chiesa di Sant’Agostino
Entrance fee | €5 for Duomo San Gimignano, free for Chiesa di Sant’Agostino
Opening hours | Mon to Fri 10 am – 7:30 pm, Sat 10 am – 5 pm, Sun 12:30 – 7:30 pm for Duomo San Gimignano
WORLD FAMOUS GELATO & PEOPLE WATCHING IN PIAZZA DELLA CISTERNA
You’ll spot it long before you taste it — the gently shuffling queue that spills out onto Piazza della Cisterna, snaking from a tiny doorway tucked beneath medieval stone. Ten, twenty people deep. All inching forward with a kind of quiet devotion towards one place: Gelateria Dondoli.
Our advice? Hit pause on whatever you’re doing, join the line, and prepare yourself. The pistachio alone is worth the wait.
Dondoli is the gelato institution in San Gimignano, a multi-time Gelato World Champion and a name locals say with genuine pride.
Everything is made in-house using natural, seasonal ingredients, and the flavours reflect that care: lavender that smells like the Tuscan countryside, saffron and pine nut (a nod to the region’s saffron history), even gorgonzola and walnut for the adventurous.
Inside, the real challenge begins: choosing. Mim stood mesmerised for a good five minutes before finally committing. We get it. It’s overwhelming in the best way.
If you love the classics, go straight for the pistachio. Creamy, nutty, and perfectly balanced, it’s one of the best scoops we’ve ever tasted — an instant reminder of why Italian gelato will ruin you for all others.
But honestly, half the joy lies in what happens after you get your cone.
Step back out into Piazza della Cisterna, San Gimignano’s largest and most beautiful square, a triangular space wrapped in medieval townhouses and bathed in warm, honeyed light. Grab a seat on the stone steps beside the 13th-century well (the piazza’s namesake) and just… be.
Watch day-trippers whirl past with their cones. See kids chase pigeons. Listen to conversations echo across the walls. Feel the hum of the town settle around you.
THE DETAILS
Where | Gelataria Dondoli, Piazza della Cisterna
Opening Hours | March to October, it is open every day from 10:00 a.m. to 1:00 p.m. and then again from 3:00 p.m. to 7:00 p.m
SOAK IN THE GORGEOUS TUSCAN VIEWS FROM PARCO DELLA ROCCA & CITADEL
San Gimignano has no shortage of beautiful viewpoints - climb Torre Grossa, and you’ll understand why photographers lose their minds here, but Parco della Rocca is its quieter, more contemplative counterpart.
Tucked behind the historic centre, this leafy park sits atop the ruins of a 14th-century fortress. The walls may be crumbling, but the atmosphere is pure magic: dappled shade, birdsong drifting through the trees, and those unmistakable towers rising behind you like something from a medieval daydream.
Wander the pathways, find a patch of sun (or cool stone wall in summer), and take in a panorama that rolls out in every direction - vineyards stitched across hillsides, olive groves catching the light, and San Gimignano’s skyline glowing above it all.
If you’re staying in town, come back for sunset. The whole landscape softens into warm golds and pinks, the silhouettes of the towers sharpen, and the crowds melt away.
And while you’re up here, it’s worth knowing that the Rocca also hosts the excellent Vernaccia di San Gimignano Wine Experience, a small tasting space dedicated to the town’s iconic white wine. A glass with that view? Yes, please.
THE DETAILS
Where | Parco della Rocca
TAKE A LONG LUNCH AT LE VECCHIE MURA
There are plenty of great places to eat in San Gimignano, but Le Vecchie Mura is the one we always find ourselves recommending - think excellent Tuscan cooking, generous pours of local wine, and a terrace view that stops you mid-sentence.
Perched along the medieval walls, the restaurant opens onto a sweeping panorama of rolling hills, vineyards, and quiet farmhouses scattered across the countryside. On a warm day, or as the sun begins to dip behind the Tuscan ridgelines, it’s outrageously beautiful. This is exactly the kind of setting you imagine when you picture long Italian lunches, and Le Vecchie Mura delivers on all of it.
Start with something simple and local: bruschetta drizzled liberally with Tuscan olive oil, or a board of pecorino with honey and walnuts.
Then dive into the regional dishes they do so well - pici with wild boar ragù, silky truffle fettuccine, or whatever homemade pasta is on special that day. The wine list leans heavily into local producers (as it should), and the tiramisu? Absolutely worth saving room for.
Just a heads-up: this is a popular spot for a reason, and the terrace books out fast.
Reserve ahead, especially in summer, and aim for an early evening sitting if you want the full golden-hour glow. It’s not the cheapest meal you’ll have in Italy, but it will be one of the most memorable.
THE DETAILS
Where | Le Vecchie Mura, San Gimignano
Cost | $$$
Opening Hours | 6 pm - 9:45 pm, closed Tuesdays
Bookings | To reserve a table, click here
EMBRACE MODERN ART AT GALLERIA GAGLIARDI
Italy is overflowing with Renaissance masterpieces — frescoes, Madonnas, saints, angels, all gazing down from gilded frames. They’re beautiful, yes… but after your fifteenth Annunciation in three days, it’s natural to start wondering where the nearest Aperol Spritz might be hiding.
That’s why Galleria Gagliardi is such a refreshing surprise.
Tucked into the heart of San Gimignano’s historic centre, this contemporary art gallery offers something completely different: an ever-evolving collection of modern works that sit in striking contrast to the medieval stone surrounding them. Step inside and you’ll find an eclectic mix of sculpture, painting, ceramics, photography, and mixed media, with each piece offering a glimpse into the minds and obsessions of today’s artists.
The curation is excellent, the space is calm and welcoming, and the range of styles is broad enough that something will inevitably stop you in your tracks.
Many works are available for purchase, too, if you’re in the market for a meaningful (or statement-making) piece to take home.
THE DETAILS
Where | Galleria Gagliardi, San Gimignano
Entrance Fee | Free (as of 2025)
Opening Hours | Daily, 11 am - 5 pm
WHERE TO STAY IN SAN GIMIGNANO
As mentioned above, we recommend extending your stay in San Gimignano and exploring more of the surrounding region.
When it comes to selecting accommodation in this captivating town, there is a delightful array of choices, from charming medieval inns and boutique hotels within the town's historic walls to rustic agriturismo (farm stays) set in the surrounding countryside.
Below are our top accommodation picks for each budget:
HOTEL LA COLLEGIATA // LUXURY
This luxurious boutique hotel, set in a beautifully restored 16th-century monastery just outside of town, offers an exquisite and romantic stay. Its location, overlooking the stunning Tuscan countryside, provides a serene and charming atmosphere. The rooms are large, styled in neo-renaissance finishings that exude old-world charm.
The best part, though, is the infinity pool with panoramic views of the countryside.
BOOK | Hotel La Collegiata
LEON BIANCO // MID-RANGE
It’s all about the location at Hotel Leon Bianco. Set on the medieval square of Piazza della Cisterna in the heart of San Gimignano's historic centre, the property retains the atmosphere of a traditional Tuscan inn while providing modern comfort.
The hotel is a 2-minute walk both from the Palazzo Comunale and from the Duomo di San Gimignano, and each room offers incredible views over the town.
BOOK | Hotel Leon Bianco
HOTEL SAN MICHELE // BUDGET
Hotel San Michele is an affordable and welcoming option for travellers on a budget. It's situated just steps from the town's iconic towers and offers clean and comfortable rooms.
However, the infinity pool elevates it above its competitors - expect exceptional Tuscan views while you enjoy an afternoon dip.
BOOK | Hotel San Michele
PLAN YOUR VISIT TO SAN GIMIGNANO
WHERE IS SAN GIMIGNANO, AND HOW TO GET THERE
San Gimignano is situated right in the heart of the province of Siena in the Tuscan region of central Italy. It lies approximately 56 km southwest of Florence and about 40 km northwest of Siena.
GUIDED TOUR
The most popular way to visit San Gimignano is via a guided tour, and there is a huge array of private tours from Florence & Siena that visit Pienza as part of a trip to Tuscany’s many Renaissance towns, including Montepulciano and Montalcino.
While tours are often fast-paced, they’re a great way to see many of Tuscany’s highlights while learning about the history, culture, and food/wine in the region.
Given the distances involved, we highly recommend a guided tour, and we’ve listed the best options below, which include transport and an English-speaking guide.
BOOK | A guided tour of San Gimignano and beyond
CAR RENTAL
If you like the freedom afforded by car rental, do as we did, and make your own way to San Gimignano
The highways & signage are well maintained, however, we still relied quite heavily on Google Maps.
FLORENCE | From Florence, the most convenient way to reach San Gimignano is by car (which you can rent in advance, here). The drive typically takes about an hour via the Siena-Florence highway.
Alternatively, if you wish to travel via public transport, take the 1hr Regional Express train to Poggibonsi, and then bus 130 to San Gimignano. The bus ride takes approximately 30 minutes.
If you’re planning a day trip, we’d highly recommend organising a guided tour like this one. It takes away the stress of driving/parking and will give you a wonderful insight into this part of the world.
SIENA | Siena is another major hub and popular day-trip starting point to San Gimignano. Again, we suggest hiring a car, in which the journey takes about an hour via the Via Cassia.
Alternatively, the quickest public transport option is via bus 130, which departs from Siena-Via Tozzi and takes around 1 hr.
BOOK | Book your car rental here
PARKING IN SAN GIMIGNANO
Parking in San Gimignano, as you could imagine for such a popular tourist attraction, is a bit of a nightmare if not planned (especially if you plan to arrive after 10 am).
Here are the best options for parking when visiting this historic Tuscan town.
Parcheggio Montemaggio | This is the main public parking lot for San Gimignano, and is located just outside the town's walls, about a 5-minute walk from the centre through Porta San Giovanni. It’s easy to find, and as you approach San Gimignano, you'll see signs directing you to Parcheggio Montemaggio. Expect to pay €2.50 for the first hour, and €2 for the second hour
Parcheggio Bagnaia Superiore | A quieter option for parking, located on the other side of town from Montemaggio. There are over 200 spaces, and the parking fee is much the same as above (€2.50 for the first hour, and €2 for the second hour). A good option in peak seasons.
Parcheggio Giubileo | An overflow carpark of sorts, Giubileo is a great alternative located around 7 minutes from the town walls. The fee is €1.50 per hour, or €6 per day, making it the cheapest carpark in town.
HOW LONG SHOULD YOU SPEND IN SAN GIMIGNANO?
San Gimignano is small and wonderfully walkable, which is why so many travellers slip in for a few hours and feel satisfied.
In a single day, you can wander the medieval centre, climb a tower or two, settle in for a long Tuscan lunch, dip into a museum, and finish with a gelato in Piazza della Cisterna. It’s compact, charming, and very easy to love quickly.
This is exactly why day trips here are so popular, and honestly, they’re great.
But if you have the luxury of time, staying one or two nights unlocks an entirely different side of the town.
The surrounding countryside is breathtaking, dotted with beautiful agriturismi, hilltop wineries, and quiet country roads made for golden-hour wandering.
When the day-trippers leave, San Gimignano exhales: the streets empty, the towers glow, and the whole place feels impossibly atmospheric.
Mornings are equally magical - soft light, cool air, and locals heading out for their first coffee of the day. It’s a completely different experience from the midday buzz.
So here’s the simple answer:
In a rush? A day trip is enough to see the highlights.
Want the full, slow-Tuscan experience? Stay one or two nights, soak in the quiet moments, and let the town breathe around you.
You won’t regret it.
WHEN IS THE BEST TIME TO VISIT SAN GIMIGNANO?
Given the ever-growing popularity of Euro-summer, we’re big believers in shoulder-season travel, and San Gimignano is a textbook example of why.
We visited in mid-September, when the heat begins to soften and the crowds thin out just enough to breathe again.
It was still busy (this is Tuscany, after all), but nothing like the wall-to-wall August surge. Paired with warm days, cool evenings, and that first hint of autumn in the vineyards, it’s a beautiful time to be here.
Spring offers a similar sweet spot: green hills, wildflowers, perfect walking weather, and a countryside waking up after winter. Expect a little more unpredictability in the forecast, but the landscapes more than make up for it.
Winter is the quietest season. Y
ou’ll have the streets and squares largely to yourself, but some attractions run on reduced hours or close entirely, and the skies tend to lean grey.
That said, there’s something undeniably charming about San Gimignano wrapped in winter stillness — moody light, empty lanes, and a slower pace that feels deeply romantic.
WANDERER TIP | If you love wine, aim for early autumn during the grape harvest. If you crave silence and easy wandering, choose late winter. But for the best balance of good weather and manageable crowds, late spring and early fall are San Gimignano at its finest.
TRAVEL INSURANCE | STAY SAFE IN ITALY
If you can't afford travel insurance, you really can't afford to travel. As the current global situation has taught many people, things can go wrong anywhere in the world - and insurance is often the only way of mitigating any issues with minimal expense or stress for you.
Here are our recommendations, based on 8+ years of full-time travel:
FOR TRAVELLERS | HeyMondo - COVID-19 coverage, comprehensive travel + medical insurance, an app with 24-hour medical support, and no out-of-pocket fees. *Get 5% off your policy by booking through our link here.
FOR DIGITAL NOMADS | SafetyWing - COVID-19 coverage, comprehensive travel & medical, and policies can be purchased while already abroad.
CAR INSURANCE | Insurance4CarHire - a great annual car insurance policy
EXPERIENCE THE BEST OF ITALY
TUSCANY | The best things to do in Florence, The best places to stay in Florence (Hotel Guide)
DAY TRIPS FROM FLORENCE | How to visit Pienza
BEST OF BOLOGNA | 12 incredibly awesome things to do in Bologna, Italy, Where to stay in Bologna, Our guide to the Asinelli Tower, Bologna Travel Tips, Best Bologna day tours, Hiking the Via Matildica in Italy’s Emilia Romagna
DOZZA | A guide to Italy’s most colourful hill town, Dozza
DOLOMITES | Our 7-day road trip itinerary for the Dolomites, where to stay in the Dolomites, how to get to the Dolomites, 7 of the best day hikes in the Dolomites, including the famous Tre Cime De Lavaredo loop, Lago di Sorapis, our guide to Lago di Braies
PHOTOGRAPHY | Love our photography? Read our detailed photography gear guide, as well as our top travel photography tips!
RESPONSIBLE TRAVEL | Responsible travel is important. REALLY IMPORTANT. Learn our top responsible travel tips to help you, your family and your friends travel more consciously around the globe
ECO-FRIENDLY PACKING ESSENTIALS | Don’t leave home without our favourite eco-friendly travel essentials
DISCOVER THE BEAUTY OF ITALY WITH OUR GUIDES
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That, and you're officially a legend.
