Best Things to Do in San Gimignano, Tuscany’s medieval town

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San Gimignano, often dubbed the “Medieval Manhattan,” captivates travelers with its striking skyline of ancient towers and rich historical allure. This picturesque Tuscan town offers a unique blend of medieval architecture, charming streets, and a vibrant cultural scene. In this guide, you will uncover the best things to do in San Gimignano, ensuring you experience its magic like a local.

What are the Best Things to Do in San Gimignano?

Whether you’re an architecture enthusiast, a history buff, or simply someone who enjoys soaking in the ambiance of a unique locale, San Gimignano has something for everyone. Winalist’s local team has create for you this guide to help you make the most of your trip, providing insights into must-see attractions, hidden gems, and local favorites.

From exploring historic squares to enjoying world-class San Gimignano wineries, you’ll find plenty of things to do in San Gimignano that will make your visit truly memorable.

Wander at Piazza della Cisterna

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Explore the heart of San Gimignano at Piazza della Cisterna, a bustling square surrounded by medieval buildings and towers. This iconic piazza, named after the ancient cistern located at its center, serves as a social and cultural hub for both locals and visitors. As you stroll around, you’ll be charmed by the historic architecture, quaint shops, and cozy cafes lining the square. Don’t forget to look up and admire the towering structures that give San Gimignano its nickname, the “Medieval Manhattan.” The square often hosts local markets and events, adding to its vibrant atmosphere. An insider tip: visit early in the morning or late in the afternoon to avoid crowds and enjoy a more peaceful experience.

Climb the Torre Grossa

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For breathtaking panoramic views of San Gimignano and the surrounding Tuscan countryside, climbing the Torre Grossa is an absolute must. Standing at 54 meters, it is the tallest tower in San Gimignano and a symbol of the town’s medieval grandeur. As you ascend the tower, you’ll pass through historical exhibits that provide intriguing insights into the town’s past.

Once you reach the top, you’ll be rewarded with an unparalleled 360-degree view. The red-tiled roofs of the town, the lush vineyards, and the rolling hills create a picturesque scene that is truly unforgettable. It’s an ideal spot for photography enthusiasts, so don’t forget your camera. Visiting early in the morning or late in the afternoon can provide the best lighting for photos and a quieter experience.

Climbing the Torre Grossa offers not just a physical perspective but also a deeper appreciation of San Gimignano’s historical and architectural significance.

Walk to Rocca di Montestaffoli

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A visit to San Gimignano would be incomplete without a walk to the Rocca di Montestaffoli, an ancient fortress offering some of the most spectacular views in the area. Located a short distance from the town center, this historic site provides a tranquil escape from the bustling streets. As you make your way up, you’ll pass through olive groves and lush greenery, creating a serene ambiance.

Once at the top, the panoramic vistas of the Tuscan countryside are simply breathtaking. You can see rolling hills, vineyards, and the iconic towers of San Gimignano in the distance. The fortress itself, though mostly in ruins, has a charming medieval atmosphere and occasionally hosts local events and festivals.

Insider tip: bring a picnic and enjoy a relaxing meal with a view.

Discover the Sant’Agostino Church

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The Sant’Agostino Church is a hidden gem in San Gimignano that deserves a spot on your itinerary. Located in a quieter part of town, this historic church is dedicated to Saint Augustine and showcases remarkable examples of Renaissance art. The church’s interior is adorned with beautiful frescoes by Benozzo Gozzoli, depicting the life of St. Augustine in vivid detail.

As you explore, you’ll notice the serene ambiance and the intricate artistry that make this church special. The altarpiece, created by Piero del Pollaiuolo, is another highlight, featuring exquisite craftsmanship and rich colors. The church also has a tranquil cloister, perfect for a moment of reflection or quiet contemplation.

Insider tip: visit during the late afternoon when the light filters through the stained glass windows, creating a magical atmosphere. Discovering the Sant’Agostino Church offers a peaceful retreat and a deeper appreciation of San Gimignano’s artistic heritage.

Stroll through Via San Giovanni

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A stroll through Via San Giovanni offers a delightful way to immerse yourself in the charm of San Gimignano. This picturesque street, one of the main thoroughfares of the town, is lined with historic buildings, artisan shops, and cozy cafes. As you wander along, you’ll find yourself captivated by the medieval architecture and the vibrant atmosphere.

Take your time to explore the various boutiques offering local products such as handmade ceramics, leather goods, and traditional Tuscan delicacies. The street also provides numerous photo opportunities with its scenic views and well-preserved facades. Don’t miss the chance to stop at a local cafe for a cappuccino or a scoop of gelato, perfect for a relaxing break.

Have lunch at Podere La Marronaia winery

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For a truly unforgettable experience, enjoy a lunch and wine tasting at Podere La Marronaia, one of the most renowned wineries in San Gimignano. Located just a short drive from the town center, this family-owned winery offers a comprehensive introduction to the world of Tuscan wines. During your visit, you’ll have the opportunity to sample a variety of local wines.

Relax at Piazza del Duomo

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Relaxing at Piazza del Duomo is a must when visiting San Gimignano. This central square, surrounded by historic towers and buildings, is an architectural marvel that offers a peek into the town’s medieval grandeur. Dominating the square is the Collegiate Church, also known as the Duomo, which provides a stunning backdrop for your visit.

Take a leisurely stroll around the piazza, soaking in the serene atmosphere and the impressive facades of the surrounding structures. The square is lined with cafes and restaurants, making it an ideal spot to sit down and enjoy a coffee or a meal while people-watching and enjoying the ambiance. The open space of the piazza allows for a peaceful respite from the more crowded streets.

Insider tip: visit in the late afternoon when the setting sun casts a warm glow over the buildings, creating a picturesque scene.

Explore the Vernaccia Wine Museum

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Exploring the Vernaccia Wine Museum is an essential activity for wine enthusiasts visiting San Gimignano. Located within the historic walls of the town, this museum is dedicated to Vernaccia di San Gimignano, one of Italy’s most celebrated white wines. The exhibits offer a comprehensive look at the history, production, and cultural significance of this unique wine.

As you tour the museum, you’ll learn about the grape-growing process, the terroir of the region, and the traditional methods used in winemaking. Multimedia displays and historical artifacts enrich the experience, providing a deeper understanding of Vernaccia’s evolution over the centuries.

Enjoy Gelato at Gelateria Dondoli

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No visit to San Gimignano is complete without enjoying gelato at Gelateria Dondoli, one of Italy’s most celebrated gelaterias. Located in Piazza della Cisterna, this award-winning gelato shop is renowned for its innovative and delicious flavors. As you approach, you’ll often find a line of eager patrons—a testament to its popularity and quality.

Once inside, you’re greeted with a wide array of flavors, ranging from classics like chocolate and pistachio to unique options such as saffron cream and Vernaccia sorbet. The gelato is made using high-quality, natural ingredients, ensuring a delightful experience with every scoop.

Insider tip: try their signature flavor, Crema di Santa Fina, a creamy concoction with saffron and pine nuts, which pays homage to the town’s heritage.

San Gimignano offers a captivating blend of medieval history, stunning architecture, and vibrant cultural experiences. From wandering through historic squares like Piazza della Cisterna and climbing the Torre Grossa for panoramic views, to exploring the rich art in the Museo Civico and discovering the serene beauty of the Sant’Agostino Church, there’s no shortage of things to do in San Gimignano. Don’t miss out on the local culinary delights, with must-try dishes that capture the essence of Tuscan cuisine.

What to do Around San Gimignano?

Whether you’re an aficionado of robust reds like Chianti or prefer the elegance of Brunello di Montalcino, there’s something for every palate. These regions are easily accessible, making them perfect for day trips. Many wineries offer guided tours and tastings, providing insights into the winemaking process and the region’s rich heritage.

Insider tip: book your wine tours in advance, especially during peak seasons, to ensure a seamless experience.

Visit the iconic town of Florence

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Just an hour’s drive or a quick train ride away, Florence is the cradle of the Renaissance and a treasure trove of art, history, and culture. Start your journey with a visit to the iconic Duomo, where you can marvel at Brunelleschi’s dome. The Uffizi Gallery is another highlight, housing masterpieces by Botticelli, Michelangelo, and Leonardo da Vinci. Stroll across the Ponte Vecchio, the city’s oldest bridge, lined with charming jewelry shops. Don’t miss the Palazzo Vecchio and the adjacent Piazza della Signoria, a vibrant square filled with statues and historical landmarks. For breathtaking views of the city, head to Piazzale Michelangelo.

Discover our guide on the best things to do in Florence as well as some top rated Florence wine tours.

Chianti: Scenic Vineyards and Wines

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A visit to the Chianti region, located about an hour’s drive from San Gimignano, is a journey into the heart of Tuscany’s winemaking tradition. Renowned for its scenic vineyards, rolling hills, and charming villages, Chianti offers an immersive experience for wine lovers. The region is best known for its Chianti Classico, a robust red wine characterized by its rich flavors and perfect balance.

Book yourself a Chianti wine tours from Winalist’s curated selection of the best wineries to visit there. Highlights include Antinori nel Chianti Classico, which provide exceptional wine experiences. The beauty of the landscape, combined with the quality of the wines, makes Chianti a must-visit destination.

Montalcino: Brunello and Medieval Charm

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Located about an hour and a half from San Gimignano, Montalcino is a picturesque town renowned for its Brunello di Montalcino wines. This medieval gem offers not only exceptional wines but also stunning architecture and breathtaking landscapes. The town itself is a maze of narrow streets, ancient churches, and charming squares, making it a delightful place to explore.

Brunello di Montalcino is one of Italy’s most prestigious wines, known for its depth, complexity, and aging potential. Many local Montalcino wineries, offer guided tours and tastings, providing a comprehensive look at the winemaking process and the unique terroir of the region.

Montepulciano: Vino Nobile and Views of Tuscany

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Montepulciano, approximately an hour and a half from San Gimignano, is famed for its Vino Nobile di Montepulciano and stunning vistas. This hilltop town offers a captivating blend of Renaissance architecture, historic charm, and exceptional wines. As you wander through its narrow, cobblestone streets, you’ll discover elegant palaces, ancient churches, and vibrant piazzas.

Begin your visit at the Piazza Grande, the town’s main square, surrounded by stunning buildings like the Palazzo Comunale and the Cathedral. Wander through the streets and explore the best Montepulciano wineries curated by Winalist.

Insider tip: climb to the top of the Palazzo Comunale’s tower for panoramic views of the Tuscan countryside, including the rolling vineyards that produce this renowned wine. Montepulciano’s combination of scenic beauty and vinous excellence makes it a must-visit destination for any wine enthusiast.

Take a day trip to Siena

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A trip to Siena offers a perfect blend of history, culture, and culinary delights, making it an unmissable part of your Tuscan adventure. Just a short 45 minutes-drive away or train ride (book your ticket here) away, Siena offers a unique experience steeped in medieval charm and rich cultural heritage.

Famous for its stunning Piazza del Campo, where the historic Palio horse race takes place twice a year, Siena’s narrow streets and picturesque squares transport you back in time. Don’t miss the awe-inspiring Siena Cathedral, with its intricate façade and beautiful interior featuring stunning artworks and mosaics.

After exploring the city’s landmarks, relax in one of the local trattorias and savor traditional Sienese dishes like pici pasta and panforte. Insider tip: Plan your visit to coincide with the quieter hours of the day to fully appreciate the city’s charm without the crowds.

Discover our perfect Florence to Siena itinerary through the Tuscan vineyards and our guide to the Best things to do in Siena to explore the best Siena wine tours.

Venturing beyond the town, the nearby wine regions of Chianti, Montalcino, and Montepulciano offer exceptional wine-tasting experiences amidst picturesque landscapes. Whether you’re a history buff, a wine enthusiast, or simply looking to soak in the charm of a unique destination, San Gimignano promises an unforgettable journey. Plan your trip well, pack thoughtfully, and immerse yourself in all that this magical town has to offer.

Good to Know to Plan Your Trip to San Gimignano

What are the best hotels to stay in San Gimignano?

When planning your stay in San Gimignano, you’ll find a range of hotels that cater to different tastes and budgets. Here are some options:
Hotel La Collegiata: For a luxurious experience, consider this 5-star hotel set in a former monastery. With its elegant rooms, beautiful gardens, and a panoramic pool, it offers a serene retreat.
Relais Santa Chiara Hotel: For a boutique experience, this 4-star hotel provides stunning views of the Tuscan countryside. It features comfortable rooms, a lovely garden, and a refreshing pool, making it perfect for relaxation.
Hotel L’Antico Pozzo: This charming 4-star boutique hotel is located within the historic town center. It combines modern comfort with medieval architecture, offering a unique and convenient base for exploring San Gimignano.

What are the best traditional restaurants in San Gimignano?

San Gimignano is home to several traditional restaurants where you can savor authentic Tuscan cuisine. Some of the top choices include:
Ristorante Perucà: A local favorite with a cozy ambiance and a menu filled with regional specialties such as wild boar ragù and truffle-infused dishes. The intimate setting and excellent wine list make it perfect for a memorable meal.
– Osteria delle Catene: Known for its rustic decor and hearty Tuscan fare, including homemade pasta, succulent meats, and rich desserts. The friendly service and warm atmosphere add to the dining experience.
– Le Vecchie Mura: Boasts breathtaking views along with delicious food. Situated along the town’s medieval walls, it offers outdoor seating where you can enjoy traditional dishes while taking in panoramic views of the surrounding countryside.

What’s the best time to visit San Gimignano?

The best time to visit San Gimignano is during the spring (April to June) and fall (September to October) when the weather is mild, and the crowds are smaller. During these months, the temperatures are comfortable, ranging from 60°F to 75°F (15°C to 24°C), making it ideal for exploring the town and surrounding vineyards.

Spring: Brings blooming flowers and lush landscapes, adding vibrant colors to your visit.
Fall: Offers the grape harvest season, providing opportunities to participate in wine-related activities and festivals.

How to get around San Gimignano?

Getting around San Gimignano is straightforward, thanks to its compact size and pedestrian-friendly layout. Here are some ways to explore the town:
On Foot: The best way to explore the town is on foot, allowing you to fully appreciate its medieval charm and discover hidden gems along its cobbled streets. Most of the key attractions, including the towers, churches, and museums, are within walking distance of each other.
– Local Buses: For those staying outside the town center, local buses provide convenient access to San Gimignano. The main bus station is located near Porta San Giovanni, one of the town’s principal gates.
– Taxis: Taxis are also available but can be more expensive.
Renting a Car: If you plan to explore the surrounding countryside or nearby wine regions, renting a car offers flexibility. However, parking inside the town is limited, so it’s advisable to use one of the public parking areas just outside the historic center.

What Are the Must-Try Dishes in San Gimignano?

San Gimignano offers a delectable array of traditional Tuscan dishes that you must try during your visit. Some iconic dishes include:
– Pappardelle al Cinghiale: A hearty pasta dish featuring wide ribbons of pasta served with a rich wild boar ragù. This flavorful dish perfectly captures the essence of Tuscan cuisine.
– Ribollita: A traditional vegetable and bread soup that’s both comforting and delicious. Made with seasonal vegetables, beans, and stale bread, this dish is a testament to Tuscany’s rustic culinary traditions.
– Pecorino Toscano: A local favorite. This sheep’s milk cheese comes in various stages of aging, each offering a distinct flavor profile. Pair it with local honey or fresh figs for a true Tuscan treat.