9 Best Things to Do in San Gimignano: Self-Guided Walking Tour + Map

Looking for the best things to do in San Gimignano? Whether you have just one day in San Gimignano or are visiting as a day trip from Florence, this self-guided San Gimignano walking tour is designed to help you navigate the medieval “Manhattan of Tuscany” efficiently. We found that starting at the southern gate is the most practical way to tackle the town’s famous towers and squares, especially if you are traveling with family. Below is the exact route we used, including a custom map and the essential logistics for parking and transport.

With the San Gimignano walking tour map ready and comfortable shoes on, the route begins at the southern edge of the town. This logical itinerary is designed to keep you moving through the best things to do in San Gimignano following the narrow medieval lanes toward the central squares without back-tracking.

Self-Guided San Gimignano Walking Tour: Route Overview

This self‑guided San Gimignano walking tour covers the town’s essential sights in an easy, straightforward route. Below is a quick overview of the main stops you’ll see along the way.

• Stroll from Porta San Giovanni to Piazza del Duomo. Just try taking in the sights and the narrow medieval streets.
• Rest a bit in Piazza del Duomo and take in the multiple medieval towers that dominate the skyline
• Taste some local gelato, especially if you have children.
• Stroll through the city park and take in the views of the surrounding countryside

Self-guided San Gimignano walking tour map. Start at Porta San Giovanni (South) and follow the red route to the medieval towers and central squares.
Yellow: Park, Red: See, Green: Walk

1. Porta San Giovanni (St. John’s Gate)

Small restaurant near Porta San Giovani inside city walls
See my photos from San Gimignano

To begin our self-guided San Gimignano walking tour itinerary, enter the historic center of San Gimignano through Porta San Giovanni and don’t forget to stop for a picture or two. This gate, is where travelers from Siena and other Southern Italian cities have entered San Gimignano for centuries. The town sits on the historic Via Francigena, a medieval road that leads to Rome. For this reason, San Gimignano was a stopping point for many Catholic pilgrims on their way to the Vatican. Take in all this history as you walk through the gate to discover all the things to do in San Gimignano.

2. Torre Dei Cugnanesi

Walk north on the narrow Via San Giovanni and look straight ahead – you’ll see an imposing tower a little ways in the distance. This is your next stop on the walking tour: Torre Dei Cugnanesi. As you walk closer, take in the medieval façades of the buildings of either side of you and stop in any shops that interest you along the way.

Torre Cugnanesi is one of fourteen remaining San Gimignano towers that compose the town’s famous skyline. Most Italian cities feature one or two significant towers, but many have been destroyed by earthquakes or during World War II. While San Gimignano once had more than seventy towers, fourteen is still an impressive number to stay standing in such a historic town.

3. Piazza della Cisterna

Piazza della Cisterna was built around an old water fountain
See my photos from San Gimignano

If you continue walking north on Via San Giovanni, you will walk under another medieval gate called Arco dei Becci and find yourself in Piazza della Cisterna, an open plaza with a large octagonal structure in the center.

This structure, which looks like a stone fountain, is the opening to an underground cistern that was constructed in 1287. The cistern lies beneath the piazza and is surrounded by more of San Gimignano’s classic medieval architecture.

This is a great spot to catch another view of both Torre dei Cugnanesi and Torre dei Becci to the south, another one of the San Gimignano towers.

4. Piazza del Duomo and Collegiata di Santa Maria Assunta

San Gimignano, Italy – Palazzo Comunale and Torre Grossa in the large square Piazza Duomo.
See my photos from San Gimignano

We continue our San Gimignano walking tour by taking Via San Matteo a few steps north-east to the Piazza del Duomo. This plaza is one of the larger ones in San Gimignano, and it features the central church in the town – the Collegiata di Santa Maria Assunta, or the Collegiate Church of Saint Mary of the Assumption. Visiting this landmark is one of the most essential things to do in San Gimignano, especially for art lovers.

Although the outside is mostly plain brick, the interior features expansive, well-preserved frescoes by artists like Domenico Ghirlandaio and Lippo Memmi, as well as striped marble details along the pillars in the nave. This church, along with a few other locations in San Gimignano, was featured in Franco Zeffirelli’s 1999 film Tea with Mussolini.

5. Torre Rognosa and Torre Grossa

Torre Rognosa is the second tallest tower in San Gimignano
See my photos from San Gimignano

While you’re in Piazza del Duomo, you’ll notice yet another imposing stone tower on the other side of Via San Matteo from the church. This is Torre Rognosa, the second tallest of the San Gimignano towers at 52 meters (almost 171 feet) tall. The tallest tower, Torre Grossa (54 meters), is also in Piazza Duomo right next to the church.

Torre Rognosa and Torre Grossa were constructed around 1200 and 1300, respectively. Towers were often built as a sign of wealth and power for significant families that lived in Italian cities, but Torre Grossa was constructed as a municipal building to serve as a symbol of San Gimignano.

6. Piazza delle Erbe and Torri dei Salvucci

A pair of medievel towers, Torri dei Salvucci are an impressive site in San Gimignano
See my photos from San Gimignano

Around the corner from Piazza del Duomo is Piazza delle Erbe, where you will find a small marketplace and two more tall towers – the Torri dei Salvucci. The Salvucci family constructed these towers to show dominance over the mayor of San Gimignano at the time, who owned Torre Rognosa. Not only did they construct two towers instead of one; both were taller than Torre Rognosa. Outraged, the mayor ordered that the Torri dei Salvucci had to be shortened so he could regain his status of owning the tallest tower in San Gimignano.

If you want to experience one of the most memorable things to do in San Gimignano, you can actually book a stay in one of the Torre dei Salvucci, which has been refurbished into an 11-story vertical apartment.

7. Rocca di Montestaffoli

A beautiful city park, Rocca di Montestaffoli provides beautiful views of the surrounding Tuscan countryside
See my photos from San Gimignano

Walk east past the church and then make a slight left until you find yourself at the Rocca di Montestaffoli, a public park on the ruins of the town’s 14th-century fortress. From here, you can see some of the most beautiful views of the surrounding countryside, from the classic Tuscan rooftops to the Chianti vineyards.

There is plenty of room here to bring a picnic, or even just a refreshing drink to take a break from walking. If you haven’t already tried it, get a LemonSoda from any convenience store or tourist stand for an especially tart, sugary beverage. Sitting in this park and taking in the views is one of the most relaxing things to do in San Gimignano.

8. Civic Museum

Old stone staircase inside the Town Hall courtyard
See my photos from San Gimignano

Make your way back to the Piazza del Duomo when you’re ready for a visit to San Gimignano’s Civic Museum. This museum is located in the Palazzo Comunale, or Town Hall. The first floor includes a few preserved meeting rooms, including the Sala Dante that was once visited by the famous poet. An art gallery on the second floor contains many works of mostly medieval Florentine and Sienese paintings.

If you’re visiting the museum, you can buy combination tickets that will get you access to a few other spots in the center of San Gimignano, including access to climb Torre Grossa.

9. Chiesa di Sant’Agostino

Finally, walk north on Via San Matteo and make a right on Via Cellolese. Shortly, you’ll arrive in front of the Chiesa di Sant’Agostino, the second largest church in the town. If you love learning about history, visiting Sant’Agostino has to be on your list of things to do in San Gimignano. The church was constructed in the 13th century, and similar to the Collegiata, is quite plain on the outside but intricately decorated within.

There are many colorful frescoes inside, including an altarpiece by Piero del Pallaiuolo, and there are multiple chapels along the nave with more paintings and statues by well-known Tuscan artists. The floor is decorated with tiles made by Andrea della Robbia, a famous ceramicist who brought glazed terra cotta into popularity in Italy.

San Gimignano Walking Tour: Questions

Planning a visit to this medieval gem often comes with a few practical hurdles. To help you prepare, I’ve answered the most common questions about navigating this San Gimignano walking tour, from parking tips to stroller accessibility.
How long does a San Gimignano walking tour take?
A relaxed self-guided route takes about 3 to 4 hours, including time to explore the main squares and viewpoints.

Where does the San Gimignano walking tour start?
Most visitors begin at Porta San Giovanni, the main southern gate and the easiest entry point from the parking areas.

Is San Gimignano easy to explore on foot?
Yes — the historic center is compact, pedestrian-only, and simple to navigate.

Do I need a guide for San Gimignano?
No. This self-guided walking tour with a map is enough to see all the major highlights. However, if you are coming from Florence or want to save time with a local guided tour, look below for some of my recommendations.

What are the must-see stops on a San Gimignano walking tour?
Key stops include Porta San Giovanni, Via San Giovanni, Piazza della Cisterna, Piazza del Duomo, Torre Grossa, and Rocca di Montestaffoli.

Is San Gimignano stroller-friendly?
The main streets are paved and manageable with a stroller, though tower climbs and some side alleys are not accessible.

What’s the best time of day for a walking tour?
Early morning or late afternoon offers lighter crowds and the best light for photos.

San Gimignano Walking Tour: Logistics & Parking

To make your visit as smooth as possible, I’ve put together the essential logistics for your San Gimignano walking tour. Below you’ll find my personal recommendations for where to stay, how to get here from Florence, and exactly where to find the best parking.

Where to stay in San Gimignano?
Hotel Bel Soggiorno has amazing location, right inside the medieval walls, so within easy walking distance from anywhere. For more of a budget option but still close to Gate San Giovanni, try Il Feudo, which is also an excellent option. You can also find other budget hotels in San Gimignano.

Coming from Florence?
Book a charming trip to San Gimignano and Siena from Florence. Visit two gorgeous medieval towns with plenty of time to explore.

Book a local walking tour.
Book this beautiful San Gimignano walking tour which will take you to all the favorite attractions.

Where to park in San Gimignano?
We drove to San Gimignano and found easy parking at Parcheggio Montemaggio 2 right next to the main Porta San Giovani entry gate. If this parking lot is full, drive down the street to the other Parcheggio Montemaggio and cross the street and walking up the hill through the small entry gate.

Is San Gimignano Worth Visiting?

Yes, absolutely! After seeing the best things to do in San Gimignano, you will get an authentic look into the Tuscan countryside, outside of large cities like Florence and Siena. San Gimignano was such an enjoyable visit for our family, that we started telling everyone about. From amazing history to the beautiful surrounding countryside, San Gimignano is a jewel of a town well worth your time to visit.

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More Tuscany Self-Guided Tours

If you enjoyed exploring the iconic medieval towers on this San Gimignano walking tour, there are plenty of other gems nearby waiting to be discovered. These self-guided Tuscany walking tours offer similar step-by-step itineraries and maps to help you experience the very best of the Italian countryside on foot.

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