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Travel bucket list idea:

Last updated: 27 March, 2024
Expert travel writer: Nicky Swallow

Sometimes dubbed the medieval Manhattan for its clutch of slim towers (visible for miles around), iconic San Gimignano is Tuscany’s most famous (and most visited) hill town. Arguably over-restored, it is nonetheless achingly pretty, a set piece of medieval palazzi, graceful piazze, narrow streets and the aforementioned towers – of which only 14 survive of an original 72.

A good way to start a visit is by climbing the 218 steps of the Torre Grossa for an overview of the town and its jumble of red rooftops. Then wander the Piazza della Cisterna (containing the town’s old well) and Piazza del Duomo – both are lovely, the latter lined with impressive palazzi.

While you’re there

Art lovers should stop by the Pinacoteca, housing a collection of 12th- and 15th-century paintings from Florence and Siena while the 12th-century Collegiata church has superb frescoes and a chapel decorated by Ghirlandaio. It’s also worth wandering into the quieter northern reaches of the town to see the frescoes by Benozzo Gozzoli in the church of Sant’Agostino.

Recommendations

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Civic Museum of San Gimignano

San Gimignano, Tuscany, Italy

Civic Museum of San Gimignano

The picture gallery houses a collection of 12th- and 15th-century paintings from Florence and Siena. Look out for a 13th-century painted crucifix by Coppo di Marcovaldo, and paintings by Benozzo Gozzoli and Filippino Lippi.

Best for ages 18+

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Collegiata di Santa Maria Assunta

San Gimignano, Tuscany, Italy

View of the Collegiate Church of Santa Maria Assunta, iconic basilica and major landmark in the historic centre of San Gimignano

The 12th-century Collegiata church has superb frescoes and a glittering interior, its vaults decorated with golden stars. The Santa Fina chapel is painted by Domenico Ghirlandaio.

Best for ages 18+

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Gelateria Dondoli

San Gimignano, Tuscany, Italy

Gelateria Dondoli

Dondoli has earned world-wide acclaim for the quality of its gelato, made from seasonal ingredients and the best local eggs, milk and cream. High season queues are insane, but it’s worth persisting to try unusual flavours such as Santa Fina (saffron and pine nuts) and Champelmo (pink grapefruit and champagne).

Best for ages 4+

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Logistics

Price: Free
Minimum age: Any
Age suitable: 18+
When: All year around

Getting there & doing it

San Gimignano is easy to visit independently, and that way you stand a better chance of dodging the tourists.

It lies about halfway between Florence and Siena, off the superstrada that runs between the two. There is a good bus service from both places; the bus stops right at Porta San Giovanni, the main entrance to the town. The journey by car is around 40 mins from Florence and 30 mins from Siena. Note that parking within the old town is impossible; there are four car parks outside the old town walls – all are just a short walk from the centre.

The tourist office is in Piazza del Duomo and carries information about a series of guided tours of the city centre and walking tours in the nearby hills, as well as details of the combined entrance tickets for the main museums.

When to do it

There is little hope of avoiding the tour groups and crowds of day-trippers if you visit in summer, especially July and August. Staying the night is one solution (most leave at the end of the day) or visit very early in the morning. Winter is the ideal season for doing the museums, but weekends should be avoided if possible.

Who to go with: organised tours

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Our selection of the best Viator tours of this attraction or activity

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

Florence

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery
Famous for a wealth of art, history, striking landscapes and outstanding produce, Tuscany really does have the best of all worlds! With only a day to spare, see the best Tuscany has to offer on this full-day guided coach trip from Florence.

Price: €85

Min age: 0

Rating 4.82 / 5 [14143 ratings]

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Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

Florence

Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing
There’s more to Tuscany than Florence. Leave the city behind and discover three other enchanting Tuscan destinations on this day trip to Siena, San Gimignano and Pisa. Take a guided tour of beautiful Siena, famous for its bareback horse race and the Gothic Siena Cathedral, and taste typical Tuscan food and wine during a 3-course lunch in a local winery or restaurant surrounded by picture-postcard Tuscan landscapes, where vineyards, rolling hills and olive groves will be your travel companions. Then, enjoy free time to explore San Gimignano, a picturesque medieval village, and Pisa, home to the UNESCO-listed Leaning Tower of Pisa.

Price: €65

Min age: 0

Rating 4.36 / 5 [3144 ratings]

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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

Florence

San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting
Discover the timeless allure of Tuscany on an immersive full-day journey! Step into the enchanting past of San Gimignano, often dubbed the "Manhattan of the Middle Ages" for its towering skyline. Traverse its cobblestone streets, steeped in history, and soak in the panoramic views of this captivating Tuscan hill village. Next, delve into the cultural richness of Siena as your expert guide unveils its treasures during a comprehensive tour of the spellbinding old town. Immerse yourself in the traditions and heritage that make Siena an icon of Italy. Explore the quaint Monteriggioni Hamlet (*). Then, prepare your senses for a typical Tuscan lunch, while savoring exquisite wines, each sip telling a tale of the region’s rich viticulture, a perfect finale to your day in Tuscany's heart. Please note that the order of the visits may change (*) November to March, the Tour does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier     

Price: €67

Min age: 0

Rating 4.19 / 5 [2449 ratings]

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Medieval Gems of Tuscany: Siena, San Gimignano and Monteriggioni

Florence

Medieval Gems of Tuscany: Siena, San Gimignano and Monteriggioni
A full day tour, taking in the key beauties of Central Tuscany including a delicious Chianti wine tasting. You'll roll through the sweeping countryside to arrive at the jewel of Siena, with its unique Square and Gothic Town Hall. Then you'll take the road for San Gimignano, the Medieval New York, and Monteriggioni - a hilltop castle with breath taking views. But it's still not over! End your visit with a Chianti winery where you savor the best of Italian wines. This is a perfect day-out to relax and replenish your spirits.

Price: €55

Min age: 0

Rating 4.37 / 5 [1056 ratings]

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Siena and San Gimignano: Small-Group Tour with Lunch from Florence

Florence

Siena and San Gimignano: Small-Group Tour with Lunch from Florence
Enjoy the high quality of this small-group tour - the perfect experience in order to discover art, history, landscapes, food and wine in a comfortable and relaxed way with more personalized attention of a small group. Depart from Florence, see the highlights of Siena through the eyes of a licensed guide, admire the marvelous Tuscan landscape, taste genuine Tuscan food paired with great wines, and finish your day relaxing in the hill top village of San Gimignano.

Price: €149

Min age: 4

Rating 4.91 / 5 [1011 ratings]

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Destination guides

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Destination guides including or relevant to this experience

Florence

Tuscany, Italy

Florence

A heady mix of incomparable Renaissance art, gorgeous palazzos, Tuscan cuisine and home-grown haute couture.

Tuscany

Tuscany, Italy

Tuscany

The astonishingly beautiful region of Tuscany has it all: art cities and ancient hill towns, high mountains and long sandy beaches, alongside luxurious hotels and some of Italy’s best food and wine.