San Gimignano Culture & history

Our most recommended San Gimignano Culture & history

From Florence: Tuscany Day Trip with Optional Lunch and Wine

1. From Florence: Tuscany Day Trip with Optional Lunch and Wine

Begin your journey of Tuscany at Florence’s central train station, where you will be greeted by your guide who will take care of you throughout the day.  Head straight to Siena, Italy’s most picturesque medieval city, whereupon arrival your guide will take you on a walking tour. Look up to admire the lovely terracotta roofs adorning the buildings and marvel at the magnificent Gothic and Romanesque architecture of the main cathedral.   Next, head to the hilltop town of San Gimignano, a UNESCO world heritage site, famous for the tower houses built in the Middle Ages. Enjoy free time here to see its splendid squares, palaces, churches, and magnificent towers. The last stop on your Tuscan excursion is a visit to Pisa and its iconic leaning tower. Take a stroll through the Piazza dei Miracoli and see other marvelous monuments, before driving back to Florence. Best of all, choose from either a small-group or private guided experience to make your trip special. Choose the lunch option to enjoy a homemade lunch paired with an informal wine tasting at a traditional wine estate in the Chianti wine region. Savor 4 regional wines at lunch and learn about their unique production techniques. Feast on an organic, farmhouse meal while you overlook the rolling vineyards under the Tuscan sun.

From Florence: Pisa, Siena & San Gimignano Day Trip with Lunch

2. From Florence: Pisa, Siena & San Gimignano Day Trip with Lunch

Discover UNESCO World Heritage Sites and taste Chianti wines on a full-day trip from Florence. Visit Pisa, San Gimignano, and Siena, and savor a traditional Tuscan lunch.  First, head to Pisa to marvel at the Piazza dei Miracoli, Pisa Baptistery, Pisa Cathedral, and, of course, the famous Leaning Tower of Pisa. Continue to a wine villa in the Chianti countryside. Enjoy a tour of the estate and learn about its history in the medieval chapel before your first tasting of Chianti Classico on the panoramic terrace. Next, relish a typical lunch accompanied by two of the estate's products, a "Riserva" and an IGP wine. After lunch, relax a while in the villa's luscious gardens before going to the medieval town of San Gimignano.  Then, follow the scenic roads to Siena for a tour of the city's monuments and piazzas. Visit Piazza del Campo — the site of the Palio di Siena horse race — and admire the cathedral's exterior in Piazza del Duomo. After some free time, return to Florence.

From Florence: Pisa, Siena & San Gimignano Day Trip with Lunch & Siena Tour with Cathedral

3. From Florence: Pisa, Siena & San Gimignano Day Trip with Lunch & Siena Tour with Cathedral

Your day begins early in the morning with a tour of Pisa, where you will admire the stunning Cathedral, the Baptistery, and the Monumental Cemetery. Take photographs next to the celebrated Leaning Tower. Continue to a winery in the foothills of San Gimignano, where you will enjoy a typical Tuscan lunch with wine tasting. After lunch, explore one of the most famous medieval hilltop villages in Italy, San Gimignano. Discover the maze of cobbled streets, picturesque piazzas, and local artisan shops. Next, admire a panoramic view of the Chianti countryside, followed by a stop in Siena. Here, a specialist guide will lead you on a walk through the city's historical center. Skip the ticket line to see the interior of the magnificent cathedral, and pass through the shell-shaped Piazza del Campo, where the Palio horse race is held twice a year. You will then return to Florence.

Siena, San Gimignano and Chianti with Wine Tasting and Lunch

4. Siena, San Gimignano and Chianti with Wine Tasting and Lunch

Along the way that will lead you to Siena, stop at San Gimignano, a small and world-famous walled town located on a hilltop, which remained intact through the centuries. It is renowned for its tall towers, wonderful frescoes and many other valuable works of art.  Here, be led to the heart of the historical center, where you will have free time to explore. Following San Gimignano, stop at the charming historical hamlet of Monteriggioni, an amazing medieval village enclosed by its famous walls, which have remained standing to this day.  Enjoy some free time to visit this village. Then, crossing the gently rolling Chianti hills, arrive at a small and typical winery where you will taste 4 fantastic wines and sample balsamic vinegar and locally produced delicacies. Upon arrival in Siena, after free time for lunch, meet your local guide. Take a comprehensive guided tour of the historic center, starting from its most beautiful square, Piazza del Campo.  Walk along the narrow medieval streets of the city, flanked by splendid palaces and historic shops, until you reach the Museum and Oratory of a Contrada (when open), where you can experience the atmosphere of the authentic and most intimate soul of the town. The “Contrade” (districts into which the city is divided) are the real core of local social life, where inhabitants of each district compete with each other, as they devote themselves to the preparation of the famous Palio horse-race.  The Museum of a ”Contrada”, as well as its Oratory, is therefore the heart of the district. It is an intimate and secret place containing historical documents and wonderful relics of the famous Palio, as well as magnificent works of art which are normally not disclosed to the public.  If you wish, your tour can include a guided visit inside the famous Siena Cathedral, built in the 12th century, to discover the beauty of its treasures and works of art.

Florence: Siena, San Gimignano, & Monteriggioni Day Tour

5. Florence: Siena, San Gimignano, & Monteriggioni Day Tour

Explore the heart of beautiful Tuscany on a full-day tour of the towns of San Gimignano and Siena, then discover the bucolic wine region of Chianti. Depart from Florence by an air-conditioned bus to your first stop, the UNESCO World Heritage Site of San Gimignano. Discover one of the most splendid examples of an Italian medieval town. Distinguished by its famous towering skyline, San Gimignano stands along the Via Francigena on the hills of the Upper Val D’Elsa. Get acquainted with the Tuscan environment with the town’s Vernaccia di San Gimignano wine, saffron, and Santa Fina pottery. Enjoy some free time to stroll through the town on your own and see its beautiful squares, architecture, churches, and side streets. Afterward, head out to a unique location in the Chianti countryside to enjoy a wine tasting. Once you hop off the bus, be guided around a splendid winery. Get introduced to the estate's fascinating history and background. Head inside the cellars to learn the secrets of Chianti winemaking together with the local host. Then enjoy a delicious wine tasting of Chianti Classico. Continue to Siena for a guided tour of its enchanting architectural styles, including the Cathedral (exterior only) and Palazzo Comunale (Municipal Building, exterior only) in Piazza del Campo. The famous shell-shaped square provides the stage for the thrilling Palio horse race, run twice every summer.

San Gimignano: Torre Grossa and Duomo Tickets

6. San Gimignano: Torre Grossa and Duomo Tickets

Enjoy this combined ticket and visit the best museums and churches in San Gimignano with an audio guide. See the Cathedral of San Gimignano, which is without a doubt one of the city's most important monuments, and climb up the Torre Grossa, San Gimignano's tallest medieval tower. See the splendid frescoes inside San Gimignano Cathedral, a real feast for the eyes. Look out for the famous Creation of Adam and Eve and Noah's arc, and listen as your audio guide explain the meaning behind the beautiful works on display. Discover the iconic 13th-century Palazzo Comunale. Walk around the Sala di Dante, which once hosted the poet Dante Alighieri. Admire the civic painting gallery, which holds masterpieces from the Sienese and Florentine schools.  Climb the 218 steps of the palazzo's 54m Torre Grossa for a spectacular view over the town and surrounding countryside. Walk around, listen to the history, and explore these impressive buildings at your own leisure. This ticket also includes a visit to the Romanesque church of St. Lorenzo in Ponte, Archaeological and Museum Contemporary Art Gallery.

Full-Day Excursion to Siena, San Gimignano & Chianti

7. Full-Day Excursion to Siena, San Gimignano & Chianti

Enjoy a full-day excursion by minivan to see the beautiful Chianti area and to visit the cities of Siena and San Gimignano.  Depart at 9:00 AM from Piazza Cavalleggeri, the meeting point located in the city center of Florence. Stop at Piazzale Michelangelo for few minutes to see the splendid panorama and then in one hour you will arrive in Siena. Take a guided tour of the city center, including Piazza del Campo and the Cathedral. There is free time to walk by yourself in the narrow and ancient streets.  Then leave Siena to arrive in Monteriggioni, an old Medieval little village. After a short stop, continue to San Gimignano where you will have free time to explore the city center on your own. San Gimignano is famous for its towers, vernaccia wine and its characteristic craft articles.

San Gimignano and Volterra: Day Tour from Siena

8. San Gimignano and Volterra: Day Tour from Siena

Start your day tour with a scenic drive from Siena to San Gimignano. Stop in Monteriggioni to see the well-preserved fortress built in the 13th century. Explore San Gimignano, admiring its many medieval towers. Recently listed by UNESCO, the town also boasts numerous artisanal boutiques. Head to a small family-run farm to enjoy lunch made with the farm’s seasonal products. Taste dishes prepared with saffron, and accompanied by Vernaccia wine. Continue to Volterra, stopping at a small alabaster workshop to see the ancient art of sculpting. In Volterra, admire the harmonious blend of Etruscan, Roman, Medieval, and Renaissance styles as you walk along the streets of the historic center.

From Florence: Tuscany Day Trip with a Private Chauffeur

9. From Florence: Tuscany Day Trip with a Private Chauffeur

Spend a day exploring the Tuscan countryside on a chauffeur-driven tour. Immerse yourself in Tuscan culture as you visit Siena's main attractions, explore an ancient hilltop town and discover one of Italy's most beloved wine regions. Your day begins with a hotel pickup to take you to the first stop on your sightseeing excursion, Siena. This historical city is a UNESCO World Heritage Site and famous for its Palio, the bareback horse race that takes around its main piazza. Visit the three must-see attractions in Siena, the Piazza del Campo, Palazzo Pubblico, and the iconic Cathedral, one of the few examples of Italian Gothic architecture. Head back to your car and continue your tour of Tuscany with a drive to the walled hilltop town of San Gimignano. Dubbed the Town of Fine Towers, San is renowned for preserving more than a dozen medieval towers. Wander through this ancient city, explore the alleys and see the Piazza del Duomo and the seven towers that surround this town square. End your day of sightseeing with a visit to the Chianti wine region. Marvel at the unforgettable landscapes with its rolling hills, vineyards, and olive groves.

San Gimignano Cathedral Entry Ticket

10. San Gimignano Cathedral Entry Ticket

Pre-book your entry ticket and audio guide to the Cathedral of San Gimignano, one of the city’s most important monuments. The walls of the church are entirely lined with frescoes that recount stories of the New and Old Testaments painted by artists of the 14th-century Sienese school. Discover the wonders of the San Gimignano Cathedral immediately upon entering. Admire the interior of the church, characterized by 14 classical Tuscan stone columns, 10 of which are round and the other four octagonal. The cycle of frescoes of the New Testament on the church’s right wall is a masterpiece by Lippo and Federico Memmi. On the left wall, spot the Stories of the Old Testament, painted in 1367 by Bartolo di Fredi. The interior also presents polychrome decorations typical of medieval churches, such as the unique painted-blue cross vault and the intrados of the arches separating the nave from the aisles decorated with a striped motif typical of the Tuscan taste. The cathedral also holds a precious Renaissance jewel, the Chapel of Santa Fina, on which three famous Florentine artists worked: an architect, Giuliano da Maiano; a sculptor, Benedetto da Maiano; and a painter, Domenico Ghirlandaio. This piece is dedicated to San Gimignano’s best-loved saint. 

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What people are saying about San Gimignano

Overall rating

4.5 / 5

based on 3,949 reviews

The first winery was no i out t so good. Even if it is small then the place could be cleaner and neater. The second one Casa Emma is wonderful. Scenery is what we wanted to see and it’s there. The wines are good and cold cuts satisfying. The crown of the tour is the third one Poggio Torselli. The gardens is beautiful and small castle is restored wonderfully.

It was an amazing tour! Both our guide Sara and driver Nikolai were excellent. The whole trip took 12-13hrs but it was totally worth it. Siena was our favorite. Walkabout Tours were really professional and organized. We had delicious pasta and wines for lunch. Highly recommend this tour.

It is a worthy day trip to the 3 most beautiful towns in Tuscany. Unless you have a car, or wise it is hard to visit 3 towns in one day hence this trip is value for money

Stephno was wonderful. Very knowledgeable and funny. Kept us entertained the entire time. You are luck to have him on your team

Excellent choices of attractions and lunch. Be prepared for alot of walking and a long day....12hours+