San Gimignano, Siena: The Ultimate Tuscany Travel Guide

History and Heritage

San Gimignano is named after St. Geminianus, and the name was changed to San Gimignano in 450 AD after Bishop Geminianus intervened to spare the castle from destruction by the followers of Attila the Hun. The town's strategic position on the Via Francigena pilgrimage route ensured its prosperity during the Middle Ages.

From being a village straddling the Via Francigena and a fiefdom of the bishop of Volterra, the medieval town developed from being located in a strategic geographical point that made it a popular route for pilgrims travelling to Rome. The town flourished through trade in agricultural products, particularly saffron and Vernaccia wine.

During the height of its power, competing families built tower houses of increasingly greater heights, and towards the end of the Medieval period, there were 72 tower houses, up to 70 metres tall. Today, 14 magnificent towers remain standing, creating the unmistakable skyline that defines San Gimignano.

UNESCO World Heritage Status

San Gimignano has been a UNESCO site since 1990 as a masterpiece of creative human genius, an exceptional example of breathtaking architecture and landscape, as well as a unique testimony to a civilisation of the past. The historic centre with its towers earned the nickname "Manhattan of the Middle Ages" and is considered a valuable universal asset.

Top Attractions in San Gimignano

The Medieval Towers

The towers are undoubtedly San Gimignano's most iconic feature. Torre Grossa is the highest tower in the city at 54 metres and one of the few you can climb to enjoy a marvellous view of the town and the surrounding hills. The climb involves approximately 218-220 steps, culminating in spectacular panoramic views.

The Devil's Tower is one of 14 remaining towers with a curious legend: the owner, returning from a trip, noticed with great surprise that the tower was taller than he had left it, an event immediately attributed to the Devil's intervention. The Torre Rognosa, the tower of the Town Hall, is the oldest and was for centuries the tallest in the town.

Piazza della Cisterna

This triangular piazza is the main square of the town, named after the cistern constructed in 1287, and is surrounded by medieval houses of different dates. The central well, dating from 1346, was the main source of water for residents. This enchanting square is home to the world-famous Gelateria Dondoli, which has won multiple ice cream world championships.

Piazza del Duomo

Connected to Piazza della Cisterna, this square houses some of San Gimignano's most important buildings. The Collegiata (Cathedral of Santa Maria Assunta) dominates the space with its impressive façade and interior covered in magnificent 14th and 15th-century frescoes.

Churches and Frescoes

The Palazzo Comunale, the Collegiata and Church of Sant' Agostino contain frescos, including cycles dating from the 14th and 15th centuries. The Chapel of Santa Fina within the Collegiata features stunning frescoes by Domenico Ghirlandaio depicting the life of the local child-saint.

San Gimignano 1300 Museum

This fascinating museum houses a detailed 1:100 scale model of San Gimignano as it appeared in the 14th century, complete with all 72 towers intact. It provides remarkable insight into how the town looked during its medieval heyday.

Food and Wine in San Gimignano

Vernaccia di San Gimignano

The town is known for its white wine, Vernaccia di San Gimignano, produced from the ancient variety of Vernaccia grape grown on the sandstone hillsides of the area. This crisp, mineral-rich wine is the only one made here and pairs perfectly with local cuisine.

Local Specialities

Local cuisine includes Tuscan soppressata and finocchiona, two rich and tasty dry-cured sausages, with the latter made from minced pork soaked in red wine and flavoured with fennel seeds. Wild boar (cinghiale) features prominently in local dishes, often served as pappardelle al cinghiale.

The town is also known for saffron, the dry aged and saffron infused Golden Ham, and pecorino cheese. The precious local saffron of San Gimignano has a protected designation of origin.

When to Visit San Gimignano

The best times for a visit are late spring when the surrounding countryside is drenched in the freshest greens imaginable and in September/October when golden light and crisp days make sightseeing a pleasure.

The summer months (June-August) see the town at its busiest with tour buses and crowds. December to February is a gamble worth taking, as the fog rolls in like a film set, lights twinkle in empty streets, and wine tastings become personal conversations.

Early morning or late afternoon visits are recommended to avoid the midday crowds. Staying overnight allows you to experience the town's magical atmosphere after day-trippers have departed.

Practical Information for San Gimignano

Parking

San Gimignano's historic centre is fully pedestrian. Main parking areas include:

• P1 Giubileo – Larger and more affordable, approximately 10-15 minutes' walk uphill
• P2 Montemaggio – More expensive but closer (5-10 minutes), convenient for those short on time

Getting Around

The town is compact and easily walkable. Most visitors can explore the main sights in 2-4 hours, though staying longer reveals the town's true character.

Siena: Gothic Grandeur and Medieval Splendour

Siena is a city in Tuscany, located in the province of Siena, known for its numerous monuments of Gothic architecture. The city rivals Florence in historical significance and architectural beauty.

Key Attractions in Siena

Piazza del Campo

This shell-shaped square is one of Europe's greatest medieval squares and hosts the famous Palio horse race twice annually. The square's unique design and surrounding Gothic palaces create an unforgettable setting.

Siena Cathedral (Duomo di Siena)

The cathedral is a masterpiece of Italian Gothic architecture with its distinctive black and white striped marble exterior. The intricate details and stunning interior took more than 50 years to complete, making it one of Tuscany's most impressive churches.

Torre del Mangia

This tower adjacent to the Palazzo Pubblico offers breathtaking panoramic views over Siena and the surrounding Tuscan countryside.

Distance and Journey Time

The distance between San Gimignano and Siena is 26 miles, with the road distance being 24.6 miles. These two cities are just 25 miles (40 km) apart, making getting from Siena to San Gimignano simple.

By Car

The fastest way to travel is to drive, which takes 42 minutes. The route typically follows the SP70 towards Colle di Val d'Elsa, then SP36 and SP1 to San Gimignano. The scenic drive winds through Tuscan hills with vineyards and olive groves.

Note that San Gimignano's entire city centre is off-limits to non-resident vehicles, so you'll need to park in designated areas outside the walls.

By Bus

There is a direct bus operated by Tiemme S.p.A. departing from Piazzale Montemaggio and arriving at San Domenico, with services every four hours operating Monday to Saturday, taking approximately 1 hour and 5 minutes. During peak summer months, there are up to 10 departures daily. Some journeys may require a change in Poggibonsi.

By Train

There is no direct train service between the two towns. The nearest train station to San Gimignano is Poggibonsi, from where you'd need to take a bus or taxi to complete the journey.

Day Tours

Numerous organised day tours operate from Florence, combining visits to both San Gimignano and Siena, often including stops at Chianti wineries and other Tuscan towns like Monteriggioni.

Located roughly midway between San Gimignano and Siena, Monteriggioni is a perfectly preserved medieval stronghold with ancient walls. This fortified village makes an excellent photo stop or brief detour when travelling between the two main destinations.

The Via Francigena connects San Gimignano to Siena through approximately 50 km of stunning Tuscan landscapes. This ancient pilgrimage route can be walked in 3-4 days, passing through olive groves, vineyards, and charming villages like Colle Val d'Elsa. The route offers an immersive way to experience the Tuscan countryside at a slower pace.

The area between San Gimignano and Siena includes portions of the famous Chianti wine region. Many visitors combine their medieval town explorations with wine tastings at local vineyards, experiencing the renowned Chianti Classico wines alongside the area's culinary traditions.

One-Day Itinerary

• Morning: Arrive in San Gimignano early (8-9 AM) to beat the crowds
• 10 AM-1 PM: Explore towers, piazzas, and churches
• 1-2 PM: Lunch with Vernaccia wine
• 2:30 PM: Drive to Siena (stop in Monteriggioni if time permits)
• 3:30-7 PM: Explore Siena's Piazza del Campo and Duomo
• Evening: Dinner in Siena featuring local Cinta Senesi and Chianti wine

Two-Day Itinerary

Day 1: Dedicate the full day to San Gimignano, staying overnight to experience evening and early morning Day 2: Travel to Siena for a full day of exploration, including climbing Torre del Mangia

Three-Day Itinerary

Add a day for Chianti wine tours, visits to smaller villages, or walking portions of the Via Francigena.

Must-Try Dishes

• Pappardelle al cinghiale: Wide pasta ribbons with wild boar ragù
• Ribollita: Traditional Tuscan bread soup
• Bistecca alla Fiorentina: T-bone steak from Chianina cattle
• Pici: Thick hand-rolled pasta typical of the Siena area
• Ricciarelli: Almond-based biscuits from Siena
• Panforte: Medieval spiced fruit cake from Siena

Wine Experiences

Beyond Vernaccia di San Gimignano, the region produces excellent Chianti Classico, Brunello di Montalcino, and Vino Nobile di Montepulciano. Many wineries offer tours and tastings, providing insight into traditional winemaking methods.

San Gimignano's towers are most photogenic during golden hour (early morning or late afternoon). The best distant views are from the surrounding countryside, particularly from the roads approaching from the south.

For Siena, the view from Torre del Mangia provides unparalleled cityscape photography. The Piazza del Campo is stunning from elevated viewing points around its perimeter.

San Gimignano

• Medieval festivals: Various events throughout summer recreating medieval life
• Harvest festivals: Celebrating the grape harvest in autumn
• Saint Fina's Feast Day: 12th March, when violets reportedly bloom on the town walls

Siena

• Il Palio: The famous horse race held twice yearly (2nd July and 16th August) in Piazza del Campo
• Siena Jazz Festival: Annual summer event
• Various medieval festivals: Throughout the year

San Gimignano offers local products including saffron, ceramics, leather goods, and regional wines. Thursday morning features a market in the main squares with fresh produce and artisan products.

Siena is known for its traditional crafts, including ceramics, leather work, and textiles. The city's shops offer higher-quality items than typical tourist souvenirs.

Both towns are well-equipped for tourists with information offices, English-speaking staff, and clear signage. However, the medieval streets and numerous steps can be challenging for those with mobility issues.

San Gimignano offers elevators from some parking areas to help reduce the uphill walk. Siena's steep streets and numerous stairs require a reasonable fitness level.

San Gimignano

• Torre Grossa entrance: €6-9
• Collegiata entrance: €4-6
• Combined museum passes available for multiple attractions
• Parking: €2-5 per hour depending on location
• Average meal: €15-30 per person

Siena

• Cathedral complex: €8-13 (various ticket options)
• Torre del Mangia: €10
• Museum passes available
• Average meal: €15-35 per person

From San Gimignano

• Volterra (30 minutes): Etruscan heritage and alabaster crafts
• San Quirico d'Orcia (45 minutes): Gateway to Val d'Orcia
• Florence (1 hour): Renaissance capital
• Lucca (1.5 hours): Medieval city with intact walls

From Siena

• Montepulciano (1 hour): Hilltop town famous for Vino Nobile
• Montalcino (1 hour): Home of Brunello wine
• Pienza (1 hour): Renaissance "ideal city" and pecorino cheese
• Florence (1.5 hours): Easy day trip by train or bus

To help preserve these precious medieval towns:

• Visit during shoulder seasons (April-May, September-October) to reduce overcrowding
• Stay overnight rather than day-tripping to distribute tourism impact
• Support local businesses and restaurants
• Respect quiet hours in residential areas
• Use public transport or carpool when possible
• Book guided tours with certified local guides
• Purchase authentic local products rather than imported souvenirs