no alt text

Travel bucket list idea:

Last updated: 24 June, 2023
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.

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+

Website >
More details >

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+

Website >
More details >

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+

Website >
More details >
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.

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

Full Day: Wine experience in San Gimignano, Siena & Monteriggioni

Florence

Full Day: Wine experience in San Gimignano, Siena & Monteriggioni
Enjoy a full-day tour visiting Tuscan villages and exploring the Chianti wine region! The village of San Gimignano, the Chianti area, and the medieval town of Siena are situated in the heart of Tuscany. Reach easily our meeting point by taking the T1.3 tram heading to Villa Costanza. Meet our staff in Florence and start your amazing journey! The first stop will be San Gimignano, a magnificent example of a Medieval urban town where you will have free time to visit the village and its splendid squares and towers. The tour will continue with the visit to the marvelous Monteriggioni medieval fortress. Don’t miss the chance to walk along the medieval wall or on the famous medieval Francigena Road. Here you will spend your free time before starting your ride to Siena. Enjoy a tasting in the Chianti Area, before coming back to Florence.

Price: €35

Min age: 0

Rating 4.44 / 5 [743 ratings]

Tour supplied by:

Viator Logo

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 4.36 / 5 [1009 ratings]

Tour supplied by:

Viator Logo

Siena San Gimignano Chianti Pisa and Lunch with Wine Tasting

Florence

Siena San Gimignano Chianti Pisa and Lunch with Wine Tasting
Your Highlights of Tuscany discovery begins with Pisa. Where we reach Piazza Miracoli, dominated by the Cathedral, the Baptistery and the Leaning Tower. From Pisa, we drive over the countryside up to San Gimignano, where a traditional Tuscan lunch with the tasting of four different wines, will be served in a characteristic Restaurant, located along the famous "Via Francigena". After lunch time, your visit continues to the discovery of a Tuscan medieval pearl, the stunning village of San Gimignano, Unesco world heritage, known for the ancient town planning still intact. Our last stop is Siena, where our local guide will take you on a guided walking tour along the small medieval streets and squares, passing the oldest bank in the world "Monte dei Paschi", the Piazza del Campo where the famous "Palio" horses race takes place twice a year, to the spectacular Cathedral. Please note that the order of the visits may change

Price: €65

Min age: 0

Rating 4.56 / 5 [444 ratings]

Tour supplied by:

Viator Logo

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

Florence

San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting
Full day Tour in the heart of Tuscany region: San Gimignano - the "Manhattan of the Middle Ages", the most famous and picturesque Tuscan hill village together with the unique experience of Siena and its traditions, thanks to the comprehensive guided tour of the stunning old town. The picturesque Monteriggioni Hamlet and the relaxing stop at a Chianti Winery for a typical Lunch which includes the guided Tasting of 3 different Wines and “vin santo”. Please note that the order of the visits may change (*) From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier     

Price: €67

Min age: 0

Rating 4.16 / 5 [2320 ratings]

Tour supplied by:

Viator Logo

San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting

Florence

San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting
Discover the easiest way to visit Siena, San Gimignano, Monteriggioni* and Chianti at a smart price. Escorted Day Trip with licensed Tour Escort on board. 3 course typical Tuscan lunch in a Chianti Winery, Wine Tasting with three different Chianti Wines, extra virgin olive oil, balsamic vinegar and “vin santo”. Free time to visit Siena, San Gimignano and Monteriggioni. Make the most of the commentary on the bus about the history, art and landscape and visit at your leisure the most famous and charming cities in Tuscany. (*) From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier     

Price: €67

Min age: 0

Rating 4.42 / 5 [117 ratings]

Tour supplied by:

Viator Logo

Florence Day Trip: Pisa, San Gimignano, and Siena with Lunch

Florence

Florence Day Trip: Pisa, San Gimignano, and Siena with Lunch
Enjoy this full-day trip to Siena, San Gimignano, and Pisa from Florence. Reach easily our meeting point by taking the T1 tram heading to Villa Costanza. Immerse yourself in the rich tapestry of Tuscany's history as you explore the three most iconic cities of the region. Discover the timeless wonder of the majestic Square of Miracles, where historical architecture and enchanting atmosphere blend into an unforgettable experience. Delight in a delectable lunch and wine tasting experience at a marvellous winery in the heart of Chianti Area. Enjoy Piazza del Campo, renowned for hosting the renowned Palio Horse Race each year. Immerse yourself in the enchanting beauty of San Gimignano, where ancient history blends with the grandeur of medieval towers, offering you an unforgettable journey in Tuscany.

Price: €78

Min age: 0

Rating 4.35 / 5 [705 ratings]

Tour supplied by:

Viator Logo

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: €79

Min age: 0

Rating 4.37 / 5 [3053 ratings]

Tour supplied by:

Viator Logo

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 [13710 ratings]

Tour supplied by:

Viator Logo

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 4.90 / 5 [969 ratings]

Tour supplied by:

Viator Logo

Wine Tasting & Tuscany Countryside, San Gimignano & Volterra

Tuscany

Wine Tasting & Tuscany Countryside, San Gimignano & Volterra
Capture the essence of Tuscany with this Small Group Shore Excursion (maximum 30 passengers) departing from the port of Livorno. Get away from the busy cities of Florence and Pisa and explore the Tuscan Countryside including Volterra and Medieval San Gimignano. Stop for a wine tasting with snacks at a local farmhouse, all included with this great experience.

Price: €170

Min age: 0

Rating 4.86 / 5 [67 ratings]

Tour supplied by:

Viator Logo

Florence to Tuscany Day Trip with Chianti, Siena & San Gimignano

Florence

Florence to Tuscany Day Trip with Chianti, Siena & San Gimignano
When visiting Florence, don’t miss a day trip to the scenic, gourmet paradise of the Tuscan countryside. On this small-group tour, visit the remarkably well-preserved medieval town of Siena, home to a magnificent cathedral and the famous Palio horse race. Indulge your taste buds with a seasonal lunch and wine tastings at a family-run farm in the Chianti region, and wander the storybook streets of the UNESCO-listed village San Gimignano. Group size is limited to 14 for a more personalized experience.

Price: €176

Min age: 0

Rating 4.71 / 5 [157 ratings]

Tour supplied by:

Viator Logo

Chianti Wine Tour with tuscan Lunch, Visit to S.Gimignano and Organic Wineries

Florence

Chianti Wine Tour with tuscan Lunch, Visit to S.Gimignano and Organic Wineries
Small Group/ Two wineries/ San Gimignano/ lunch/ guided wine tastings/ gelato world champion/ piazzale Michelangelo and more.. First we tour vineyards and cellar of an organic farm in the heart of the Chianti region, receiving an up close look at the production and ageing process of the Chianti wines and learning about the secrets of the extra virgin olive oil making. This experience includes a  wine tasting and the opportunity to buy for cheap the best tuscan wines. Our trip continues on to the  medieval town of San Gimignano, where you will also have the chance to try the famous world champion Dondoli gelato. We then move on to a second winery where we enjoy an authentic  tuscan lunch, combined to a wine tasting class. On our way back we stop at  Piazzale Michelangelo, in the top ten of the most romantic spots in Europe.

Price: €190

Min age: 0

Rating 4.92 / 5 [633 ratings]

Tour supplied by:

Viator Logo

Horseback ride, visit to S.Gimignano, tuscan lunch, wine tasting, Chianti winery

Florence

Horseback ride, visit to S.Gimignano, tuscan lunch, wine tasting, Chianti winery
Explore the Tuscan countryside in a most delightful way... on horseback! This horse riding adventure requires absolutely no prior experience and will give you the opportunity to enjoy the most authenitc sights, sounds and smells of the Chianti region away from the busy city! We ride through lush vineyards, native woods, olive groves and rolling hills to offer you a collection of breathtaking and unforgettable views. After the visit to the renowned medieval town of San Gimignano we enjoy a typical tuscan lunch combined with a guided Chianti wine tasting at a local winery. If you do not want to ride a horse, you can still come and enjoy the tour with a 20 euros discount! So, while your friends go on the horse ride you can enjoy a beautiful walk around the farm, discover the art of beekeeping and honey production, learn about saffron harvesting and cultivation, know about the olive oil making process and enjoy some drinks. We meet at 9 am in Florence, via Curtatone 9

Price: €190

Min age: 0

Rating 4.85 / 5 [260 ratings]

Tour supplied by:

Viator Logo

Small-Group Siena and San Gimignano with Dinner in a Boutique Winery

Florence

Small-Group Siena and San Gimignano with Dinner in a Boutique Winery
Embark on a captivating journey through Siena, San Gimignano, and Chianti's countryside. Conclude with a mesmerizing sunset and dinner. Once, Siena rivaled Florence in power and allure. Begin from Florence in a comfy minivan with an English-speaking driver, journeying to Siena. Discover Siena through a guided walking tour, exploring Piazza del Campo where the famed Palio horse race takes place. Learn about the Contrade, medieval city districts competing in Palio. Enjoy a surprise tasting in Siena. Next, reach San Gimignano, renowned for medieval skyscrapers and preserved tower houses, crafting a unique skyline. After leisure in San Gimignano, witness a breathtaking sunset. Relish wine tasting and a traditional Tuscan dinner in Chianti. Explore ancient cellars, gaining insight into wine production. A remarkable experience, embracing Tuscan gems, gastronomy, and wines. Numbers are limited to 16 on this small-group tour, ensuring a personalized experience.

Price: €199

Min age: 0

Rating 4.27 / 5 [103 ratings]

Tour supplied by:

Viator Logo

Semi Private Deep Wine Chianti and San Gimignano from Florence

Florence

Semi Private Deep Wine Chianti and San Gimignano from Florence
This tour is designed to make your Tuscan wine-tasting dreams come true. You'll be able to see all the classic postcard-perfect landscapes of Tuscany while you travel from one cellar to another. You will visit two wineries and have the opportunity to taste a selection of high-quality Tuscan Chianti wines. Lunch is included. If you're a fan of good wine, excellent food, and landscape photography, you'll love this tour. And you'll also have the chance to visit one of the most beautiful villages in the world: San Gimignano, famous for its majestic towers and delicious ice cream. Our tours feature the latest models of Mercedes vans, complete with air conditioning, WiFi, and an iPad for each couple and one bottle of water for every tour member and of course a Bottle of Prosecco White Wine for a travelling happy hour at the end of the tour!

Price: €199

Min age: 0

Rating 4.81 / 5 [101 ratings]

Tour supplied by:

Viator Logo

Chianti and San Gimignano - 2 Wineries with Pairing Lunch

Siena

Chianti and San Gimignano - 2 Wineries with Pairing Lunch
Our driver guide will collect you at your accommodation, ( No meeting points, we pick you up at your place! ) setting off toward the heart of Chianti Classico. Experiences 1 day exciting trip in the heart of Chianti and visit the most beautiful village in the region. > Step 1 - Charming boutique winery in Chianti > Step 2 - Visit of Monteriggioni and/or San Gimignano > Step 3 - Pairing lunch in the most famous winery in the area Tour Length: 7/8 hours. Departure Time: From Florence 9.30 AM - From Siena 10.00am Note: During this excursion, transport will be made in a Mercedes 9 seat minivan which offers the maximum comfort, with air-conditioning, large panoramic windows and comfortable seats. Unless you don't specify you want to remain private, is possible to be joined with some other people in the party  ( maximum 1 van ) Popularity: *****  (best seller wine and food tour in Tuscany)

Price: €249

Min age: 12

Rating 4.85 / 5 [34 ratings]

Tour supplied by:

Viator Logo

Private Tuscany Tour: Siena, Pisa and San Gimignano from Florence

Florence

Private Tuscany Tour: Siena, Pisa and San Gimignano from Florence
Experience a full-day, private tour of the Tuscan gems, Pisa, Siena, and San Gimignano. Let your private driver do all the paperwork and explore Siena, Pisa and San Gimignano at your own pace. With hotel pickup and drop-off from Florence, you will be able to sit back and enjoy the picture postcard Tuscan countryside surrounding you and your travel companions. Make the most out of this private experience with a private and knowledgeable driver at your full disposal. Design with him the itinerary of your dreams!

Price: €474

Min age: 0

Rating 4.81 / 5 [105 ratings]

Tour supplied by:

Viator Logo

PRIVATE Full-Day Siena, San Gimignano and Chianti from Florence

Florence

PRIVATE Full-Day Siena, San Gimignano and Chianti from Florence
• EXPERIENCE FOR YOUR PRIVATE GROUP • With this fascinating tour you will discover a unique part of Tuscany in a private day-trip from Florence. With an expert local driver/guide, immerse yourself in the renowned Chianti wine region and explore the cities of Siena and San Gimignano. You will tour historic landmarks such as Piazza del Campo in Siena, home to the annual Palio, and the medieval towers of San Gimignano. Add an optional, unforgettable lunch to savor traditional Tuscan wines and specialties in a local organic farm or winery! • 8/9-hr Full-Day private tour of Tuscany • Visit the medieval cities of Monteriggioni, San Gimignano and Siena • Hear live commentary of the wine cellars by your guide • Taste Craft Chianti Classico wine at a local vineyard • Pick-up and drop-off at your Hotel or at the address provided • Travel in a Mercedes-Benz minivan

Price: €620

Min age: 0

Rating 5 / 5 [134 ratings]

Tour supplied by:

Viator Logo

Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence

Florence

Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence
*Experience for your private party* Explore the art, culture and medieval history of Italy on this private 8 hrs tour. Discover the delights of Tuscany on a private day trip from Florence. With a knowledgeable English-speaking private driver, travel through the renowned Chianti wine region to visit the towns of Siena, the fortress of Monteriggioni and San Gimignano. See world-famous landmarks like Siena’s Piazza del Campo, home to the annual Palio horserace, and the medieval hilltop towers of San Gimignano. • Our drivers are all extremely familiar with Tuscany and with the main destinations. They will always share historical information, curiosities and traditions about the area of the sightseeing and they are available at any needs. * With agreements during the reservation we can organize lunch in wine cellars or in the farms. This is a highly recommended experience, especially for the wine lover.

Price: €650

Min age: 0

Rating 4.91 / 5 [231 ratings]

Tour supplied by:

Viator Logo

Private Guided Tour: Siena, San Gimignano and Chianti Day Trip from Florence

Florence

Private Guided Tour: Siena, San Gimignano and Chianti Day Trip from Florence
Experience for your private group. Come with us for an unforgettable day spent visiting Siena with a professional city guide and the Chianti area accompanied by one of our expert English speaking drivers born and raised in Tuscany. -During the 8hr tour you will explore the Gothic city of Siena with its famous shell-shaped Piazza del Campo and the gorgeous cathedral, followed step by step by a licensed TOUR GUIDE! If you love to visit the cathedral there will be to pay at the guide directly euro 5 per person or euro 7pp with priority -In the afternoon you will have the opportunity to visit some of the most famous vineyards, or unknown small family businesses, see their cellars and taste their excellent wines and food. -Then explore the wonderful medieval city of San Gimignano.

Price: €880

Min age: 0

Rating 4.70 / 5 [17 ratings]

Tour supplied by:

Viator Logo

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.