Standing amid the rolling hills of Tuscany, I found myself gazing up at the medieval skyline of San Gimignano, a UNESCO World Heritage site known for its remarkable stone towers. These ancient structures tell stories of wealth and power from centuries past, rising dramatically above the terracotta rooftops like a medieval Manhattan.
The Torre Grossa, at 54 meters, is the tallest and most rewarding tower to climb in San Gimignano. It offers spectacular 360-degree views of the town and surrounding Tuscan countryside from its 218 steps.
My recent tower-climbing adventures with my family revealed that not all of San Gimignano’s towers are open to visitors. While the town once boasted 72 towers, only a handful remain today, and fewer still allow visitors to scale their ancient staircases. The Torre Grossa stands out not just for its height but also because it provides the most comprehensive panoramic views, allowing you to see the picturesque landscape that makes this region of Italy so captivating.
When planning your visit to this medieval gem, consider starting with the Torre Grossa for the best introduction to the town’s layout. I noticed that morning visits offer softer light for photographs, while late afternoon climbs reward you with golden Tuscan sunsets that transform the countryside into a painting.
The climb is moderately challenging but definitely manageable for most visitors, including families with children who are ready for a bit of adventure.

Historical Context of San Gimignano’s Towers
San Gimignano’s skyline is defined by its remarkable medieval towers that once symbolized wealth and power in this Tuscan hill town. These architectural marvels tell a fascinating story of competition, prosperity, and medieval urban life.
Medieval Marvels: The Rise of the Towers
Walking through San Gimignano today, I’m always struck by how these towers transform the town into a medieval skyscraper city. Back in the 11th to 13th centuries, wealthy families built these towers as symbols of their power and prestige.
At the height of tower construction, an astonishing 72 towers crowded the small area within the city walls. Imagine the competition between rival families trying to outdo each other with taller and more impressive structures!
The towers served practical purposes too. They provided defensive positions during conflicts and safe storage for valuable goods. Some reached heights of 70 meters (about 230 feet) until the city council stepped in with a height restriction – no tower could surpass that of the Palazzo Comunale (city hall).

Architectural Wonders: Understanding Medieval Manhattan
The nickname “Medieval Manhattan” perfectly captures what makes San Gimignano so special. These towers created one of Europe’s first vertical cities.
Building these structures was no small feat. Using basic medieval technology, craftsmen created surprisingly sturdy towers that have withstood centuries. The construction typically featured thick stone walls that tapered as they rose higher.
Families lived vertically in these towers, with different floors serving different purposes. Lower levels often housed shops or storage, while upper floors provided living quarters with more light and better views. The very top sections typically served as lookout points.
What’s remarkable is that 14 of these medieval skyscrapers have survived to this day. The most famous is Torre Grossa, the tallest remaining tower at 54 meters (177 feet).

Cultural Heritage: Towers as a Testament to Prosperity
San Gimignano’s towers reflect the town’s golden age during the Middle Ages. The city grew wealthy as a crucial stop along the Via Francigena, the important pilgrimage route to Rome.
This strategic location made it a thriving trade center. Local families amassed fortunes through commerce, particularly in saffron (known as “red gold”) and the region’s excellent wines. With wealth came the desire to display status through tower construction.
The town’s history stretches back even further to its origins as an Etruscan village before becoming a medieval powerhouse. In 1990, UNESCO recognized San Gimignano’s historical significance by declaring its historic center a World Heritage Site.
Today, these towers aren’t just tourist attractions – they’re living monuments to medieval ingenuity and ambition. Each one tells a story of rivalry, craftsmanship, and the human desire to reach for the sky.

A Tour of the Towers: Tower Climbing Essentials
When exploring San Gimignano’s famous towers, knowing what to expect makes all the difference between an exhausting climb and a rewarding adventure. These medieval skyscrapers offer incredible views but require some planning.
Torre Grossa: The Tallest Tower
Torre Grossa stands as the crown jewel of San Gimignano at 54 meters (177 feet) tall. Built in 1298, it’s the tallest tower you can climb in town.
I paid 9 euros for admission, which includes access to the adjacent museum. While some visitors find the museum underwhelming, I think it provides helpful context for understanding the town’s history.
The climb involves 218 steps up a series of staircases. I’d recommend wearing comfortable shoes with good grip since some steps are worn smooth from centuries of use.
Once at the top, I was rewarded with breathtaking 360-degree views of the Tuscan countryside. The panorama includes rolling hills, vineyards, and the town’s remaining towers jutting upward like medieval skyscrapers.

Tips for Families and Solo Adventurers
Tower climbing in San Gimignano can be challenging but doable for families. I’ve seen parents with children as young as seven manage the climb successfully.
For families, I recommend:
- Visiting early morning to avoid crowds and midday heat
- Bringing water bottles (the climbs get warm)
- Taking breaks on the landings between flights of stairs
- Setting realistic expectations about the climb’s difficulty
Solo travelers like me can easily fit multiple tower climbs into one day. I found the towers less crowded in late afternoon, offering more space to enjoy the views and take photos without feeling rushed.

Navigating the Town: Routes and Recommendations
San Gimignano’s compact historic center makes tower-hopping relatively straightforward. I started my tour at Torre Grossa in the main square (Piazza del Duomo) and worked outward.
The Torri dei Salvucci, twin towers near the center, make an interesting sight even though they’re not open for climbing. I found them fascinating as examples of how wealthy families competed by building ever-taller towers.
For the most efficient route:
- Begin at Piazza del Duomo with Torre Grossa
- Walk toward Porta San Giovanni
- Circle back to view Torre del Diavolo (Devil’s Tower)
During my walk between towers, I discovered charming shops and cafés perfect for rest breaks. The town’s stone streets can be steep, so I paced myself while moving between climbing locations.

Iconic Views and Photo Opportunities
The towers of San Gimignano offer some of the most breathtaking panoramas in all of Tuscany. Each vantage point provides a unique perspective on the medieval town and the surrounding countryside that has remained largely unchanged for centuries.
Vernaccia Vineyards: A Tuscan Panorama
From the tops of San Gimignano’s towers, I’ve been mesmerized by the patchwork of Vernaccia vineyards that stretch to the horizon. These vineyards produce the famous Vernaccia di San Gimignano wine, the region’s signature white wine with protected status.
The best view of these vineyards comes from the western side of Torre Grossa, where the afternoon sun bathes the landscape in golden light. In spring, the neat rows of green vines create geometric patterns against the earth. During autumn, the countryside transforms into a tapestry of amber, gold, and russet.
For wine enthusiasts, photographing these vineyards from above offers context to the wine-tasting experiences available in town. I recommend visiting between May and October when the vineyards are most vibrant.

The Piazzas Below: Cisterna and Duomo
Looking down from the towers provides a fascinating bird’s-eye view of San Gimignano’s bustling piazzas. Piazza della Cisterna, with its distinctive triangular shape and ancient well at its center, appears like a medieval stage set.
From Torre Grossa, I could see the intricate layout of Piazza del Duomo with its remarkable Collegiate Church. The geometric patterns of the stone pavement become visible from above, a detail impossible to appreciate at ground level.
Morning visits offer the best light for photography of the piazzas, before they fill with tourists. The shadow play of towers across the squares creates dramatic compositions around 9-10 AM.

San Gimignano from Above: Best Spots for Photography
The Rocca di Montestaffoli, the ruins of a former fortress, provides an excellent external view of San Gimignano’s tower skyline. Though not as high as climbing a tower, this spot offers the perfect vantage point to capture the town’s famous silhouette.
For the most iconic tower shots, I found Torre Grossa unbeatable. Its height advantage lets you capture other towers against the backdrop of rolling hills. Bring a zoom lens to photograph distant landmarks like the towers of Volterra on clear days.
The best photography times are during the golden hour – the hour after sunrise or before sunset. During these times, the stone towers glow with warm light, creating a magical atmosphere that’s worth the early wake-up call.

Cultural Attractions Beyond the Towers
While San Gimignano’s iconic medieval towers define its skyline, the town offers a wealth of cultural treasures waiting to be discovered at ground level. From remarkable religious art to world-class cuisine and contemporary creative expressions, there’s much more to experience in this Tuscan gem.
Sacred Art and History: Museums and Churches
The Museum of Sacred Art houses an impressive collection of religious artifacts and paintings that tell the story of San Gimignano’s spiritual heritage. I was particularly moved by the vibrant 14th-century frescoes and intricate gold leaf altar pieces that showcase the town’s historical importance.
For those interested in a different kind of history, the Torture Museum offers a sobering look at medieval justice practices. It’s not for the faint-hearted, but provides fascinating historical context.
The town’s churches are magnificent repositories of art and faith. The Collegiate Church features stunning frescoes depicting biblical scenes that literally took my breath away. The details in these centuries-old paintings remain remarkably vivid.
San Gimignano’s Duomo contains masterworks by Ghirlandaio and other Renaissance artists. I recommend visiting early morning to appreciate the sacred atmosphere before the crowds arrive.

Taste of Tuscany: Cuisine and Wine
San Gimignano’s culinary scene is a cultural attraction in itself. The local specialty, Vernaccia di San Gimignano, is a crisp white wine that pairs perfectly with Tuscan dishes. I enjoyed a guided tasting at a local vineyard where I learned about its unique characteristics and ancient production methods.
Ristorante Dorando offers authentic Tuscan cuisine with stunning views of the countryside. Their handmade pasta with wild boar sauce is simply unforgettable!
Local Specialties to Try:
- Pici pasta with ragu
- Pecorino cheese with local honey
- Ribollita (hearty vegetable soup)
- Fresh porcini mushrooms (seasonal)
The town also hosts several food festivals throughout the year celebrating seasonal harvests. These events provide a wonderful opportunity to experience local traditions while savoring exceptional flavors.

Living Art: San Gimignano’s Modern Spirit
Despite its medieval appearance, San Gimignano embraces contemporary artistic expression. Small galleries featuring modern art are tucked between historic buildings, creating an interesting dialogue between past and present.
During summer months, the main square transforms into an open-air venue for concerts, performances and art installations. I stumbled upon a string quartet playing at sunset—the music echoing off ancient stones created a truly magical experience.
Local artisans continue traditional crafts with modern interpretations. Ceramic studios, leather workshops, and jewelry makers offer unique pieces that make meaningful souvenirs.
The town also hosts an international contemporary art festival that attracts artists from around the world. Walking through temporary exhibitions set against medieval backdrops creates a fascinating juxtaposition that highlights San Gimignano’s living cultural heritage.

Planning Your Visit: Practical Tips
Making the most of your tower-climbing adventure in San Gimignano requires some thoughtful planning. I’ve gathered essential information to help you enjoy this medieval Tuscan gem without the common pitfalls many visitors face.
When to Visit: Finding the Perfect Season
I’ve found that spring (April-May) and fall (September-October) offer the perfect balance of pleasant weather and fewer crowds in San Gimignano. Summer brings intense heat and tourist crowds, making tower climbing less enjoyable and causing long lines at Torre Grossa.
Winter visits have their charm too. The town feels more authentic when fewer tourists are around. I once climbed the Torre Grossa in February and had the entire viewing platform to myself!
For the best lighting for photos, I recommend visiting towers in the early morning or late afternoon. The golden Tuscan light creates magical views across Chianti’s rolling hills.
Pro tip: Many towers close between 1-3 PM, so check current opening hours at the tourist office near Porta San Giovanni.

Accommodations and Local Tips
Staying overnight in San Gimignano transformed my experience. Once day-trippers leave, the medieval streets become wonderfully quiet.
Accommodation options:
- In town: Charming but pricier
- Nearby agriturismo: Rural farm stays with authentic Tuscan hospitality
- Siena or Florence: Good bases for day trips (30-60 minutes by car)
I recommend exploring Via San Giovanni early in the morning before shops open. For dinner, avoid restaurants directly on Piazza Cisterna. Walk a few streets away for better prices and more authentic food.
Transportation is important to consider. Parking outside the walls costs €2/hour or €20/day. The bus from Siena or Florence is more economical if you’re not exploring the countryside.

Sustainable Tourism: Respecting the Heritage
The medieval towers of San Gimignano represent fragile history that requires our respect. I always follow posted guidelines when climbing. I never touch the ancient stonework unnecessarily.
Some practical ways I practice sustainable tourism here:
- Bring a reusable water bottle. (There are public fountains near Piazza Cisterna.)
- Visit lesser-known towers to reduce crowding at popular spots.
- Support local businesses outside main tourist areas.
- Learn a few Italian phrases. Shopkeepers in San Gimignano greatly appreciate the effort.
The town has implemented visitor management systems during peak seasons. I recommend booking tower entry times online when possible, especially for Torre Grossa.
Remember that real people call this beautiful UNESCO site home. I try to keep noise down. I especially do this when exploring the quieter streets around the main squares.