San Gimignano
Walking Tours

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Our most recommended San Gimignano Walking Tours

San Gimignano, Siena, Chianti Guided Tour from Florence

1. San Gimignano, Siena, Chianti Guided Tour from Florence

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.

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San Gimignano Area: Wine Tasting Experience

2. San Gimignano Area: Wine Tasting Experience

A few steps from San Gimignano, there is a splendid family-run winery. Here, you can taste typical Tuscan products including wine and tasty local croutons. Do not miss the opportunity to learn how to combine Tuscan wine with appetizing foods and find out how wines are produced in a real cellar. You will visit the cellar, the vineyards, and all the places where the wine comes to life. Listen to stories, and hear about winemaking processes. You'll discover that Tuscany and Chianti are areas to be loved and protected. As you discover the secrets of wine and grapes, you'll also learn about the best food pairings.  You can choose between two unique experiences:  Tasting of four wines accompanied by snacks of typical products preceded by a tour of the cellars and vineyard Lunch and tasting of four wines preceded by a tour of the cellar and the vines

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San Gimignano: Private Organic Winery Tour & Tasting

3. San Gimignano: Private Organic Winery Tour & Tasting

Enjoy a 1.5-hour visit to Podere la Marronaia, a small family-run farm in San Gimignano, dedicated to the cultivation of grapes and olives and production of organic wines and extra virgin olive oils. In 2016, the fields were converted to the more sustainable form of biodynamic agriculture. The purpose was to produce wines and extra virgin olive oil using authentically grown Tuscan grapes and olives. Take a short walk from central San Gimignano to Sosta Alle Colonne, the cellar and the tasting venue. Your visit will not be just a wine tasting, but an introduction to the world of Tuscan wines. Experience the family's passion for the land and its products.

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San Gimignano: Vineyard and Cellar Tour with Wine Tasting

4. San Gimignano: Vineyard and Cellar Tour with Wine Tasting

Begin your wine tasting experience with a tour around the vineyards that surround the winery. While touring the vineyard, learn about the agronomic phases of the vineyard. Once you have toured the vineyard, you'll visit the wine cellar, where you’ll learn about the vinification process and aging techniques. Move into the tasting room, where you’ll get a chance to learn about wine and food pairing before starting your wine tasting. The wine tasting will include all the wines in the vineyard production. The wine tasting will be paired with local cured meats, cheese, and olive oil. Taste a variety of wines including, Vermentino IGT, Vernaccia di San Gimignano DOCG, Vernaccia di San Gimignano Riserva DOCG, Chianti DOCG, Chianti Riserva DOCG, Japigo, IGT Supertuscan, and Vin Ssanto del Chianti DOC.

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Private Guided Tour in San Gimignano

5. Private Guided Tour in San Gimignano

Enjoy a 3-hour walking tour and where you'll discover the unique histories of noble families that lived once in San Gimignano. At Cistern Piazza, taste a famous ice cream that has won many prizes. At the Piazza Duomo square, you will admire the Public Palace and the wonderful Cathedral. If you choose to visit the palace, you will explore the Civic Museum and the highest tower in the town, from where you can take wonderful pictures of the surrounding landscapes. If you prefer to enter the Cathedral, you will be able to admire well-preserved frescoes. Witness panoramic views from the Montestaffoli Fortress where the Vernaccia Museum is also situated. DOCG white wine is produced in this area. The guide will suggest that you have a toast in a wine shop (at a little extra cost).

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San Gimignano: 1.5-Hour City Highlights Walking Tour

6. San Gimignano: 1.5-Hour City Highlights Walking Tour

Meet your guide for a city highlights tour in front of the grand Porta San Giovanni, the main gate, and continue along Via San Giovanni, once a pilgrimage route to Rome. Discover the history of the economic center Piazza Della Cisterna, as well as the Piazza del Duomo, the religious and political center of the town.   Then, admire the medieval 'beautiful towers,' and hear stories about the process making of saffron - the so-called 'gold of San Gimignano.' On this tour, you'll also learn about the famous locally produced Vernaccia wine. Your journey will end at the main square - the Piazza del Duomo.

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From Florence: 4-Day Tuscany Highlights Tour

7. From Florence: 4-Day Tuscany Highlights Tour

Day 1: After checking in to your hotel, begin your day with a guided tour of the Uffizi Gallery and learn more about the oldest and most famous art collection in the world.  Following the Uffizi, join a tour of Florence's most iconic streets and squares with a professional guide. Stroll through the stunning Santa Maria del Fiore Cathedral, the Old Bridge, the Signoria Square with its replica of Michelangelo’s David, the Republic Square and more. Day 2: Crossing the beautiful Chianti hills, arrive at the walled town of Monteriggioni. Drink in the town's century-old history and relive the Medieval atmosphere before continuing to Siena, famous for its splendid examples of Gothic architecture, and enjoy a light lunch in a cozy restaurant where you can try traditional Tuscan products.  Next, drive to San Gimignano, a UNESCO World Heritage Site famous for its wine. At the end of the day, head to the Chianti area and marvel at its picture-perfect landscapes. Sample the region's best red wine in a rustic wine estate along with home-made aperitifs and olive oil tastings. Day 3: After breakfast, begin the journey to Cinque Terre National Park for an unforgettable day in one of the most enchanting landscapes in the world. Discover five villages suspended between sea and land, where you can sunbathe or swim in one of the area's many beaches before taking the boat to Vernazza, a seaside town surrounding a small natural port. Day 4 Today, enjoy a guided tour of the Florentine Dome and enjoy panoramic views of the entire city from its peak. Afterward, enjoy a guided tour of the Accademia, where you can see Michelangelo's masterpiece, David.

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From Livorno: Shore Excursion to Chianti and San Gimignano

8. From Livorno: Shore Excursion to Chianti and San Gimignano

Discover the beauty of the Chianti wine region on this shore excursion from Livorno. After getting picked up from the port, enjoy a relaxing 1.5-hour drive through the picturesque Chianti countryside to reach your first stop, the charming market town of Greve-in-Chianti where you can visit Macelleria Falorni, a specialist in wild boar and pecorino cheeses and one of the best butchers in Italy. Later, as you cross the hills to Montefioralle, the tiny hamlet where Amerigo Vespucci was born, enjoy a wine tasting tour at a small family-owned estate. Your journey will then take you through the Antinori vineyards at Badia a Passignano to relax over a convivial Tuscan lunch at a little osteria hidden away amongst these rolling hills. After lunch, stop at the World Heritage site of San Gimignano with its unforgettable skyline of towers. The town is renowned for its white Vernaccia di San Gimignano wine and the Gelateria di Piazza, where Sergio Dondoli creates award-winning gelato with flavors including Vernaccia wine sorbet. Get dropped off back at your ship in the afternoon with plenty of time before departure.

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San Gimignano 2-Hour Private Guided Tour from Siena

9. San Gimignano 2-Hour Private Guided Tour from Siena

San Gimignano is an authentic gem amongst the small towns and villages in the Tuscan countryside. It's quite unique, due to its beautiful medieval architecture and the surprising preservation of about a dozen of its tower houses. For this and other reasons, the "Historic Centre of San Gimignano" has been declared a UNESCO World Heritage Site. The well-preserved buildings include notable examples of both Romanesque and Gothic architecture, with outstanding examples of secular buildings as well as churches. During this guided tour you'll see the most beautiful and important sites oft the village, such as Palazzo Comunale, the Collegiate Church and Church of Sant' Agostino. You'll walk through the typical small streets of the village and see the pictoresque Piazza della Cisterna, Palazzo Pubblico and Torre Grossa. Guests are advised to bring their cameras along!

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San Gimignano: Vernaccia Wine Tasting Experience

10. San Gimignano: Vernaccia Wine Tasting Experience

Sample some of the winemaking excellence of the San Gimignano territory. Go on a wine tasting of Vernaccia di San Gimignano DOCG d'annata wines. Benefit from the presence of professional sommeliers and connoisseurs of the evolution of this wine-producing area, its wines, and the people who produce them. Be comfortably seated and safely distanced in the wine tasting room. Enjoy a sensory wine tasting of the Vernaccia di San Gimignano DOCG reserve. Sample a white wine that will amaze you both with its taste and its story. Continue to a wine tasting of the San Gimignano DOC red wine. Treat your taste buds to this fascinating wine from the territory. Enjoy a pairing of savory foods produced in the region.

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Other Sightseeing Options in San Gimignano

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What people are saying about San Gimignano

Overall rating

4.6 / 5

based on 994 reviews

The towns are spectacular. It's a beautiful area, well worth seeing. The visit was a bit rushed, but if you want a convenient arrangement, where you don't have to worry about planning your trip, driving, finding a parking a spot etc., it's a good option. The driver Eddy was nice, spoke many language and also acted a bit as a guide during the drive. The only suggestion I have is advising the customers in advance that having lunch in Siena might be tricky when there are a lot of tourists around. It took us almost an hour to find seating and to be able to eat a prepackaged sandwich at a small cafe. Everything everywhere seemed all booked up. But otherwise, this day trip was the highlight of our weekend and we recommend it.

Incredible tour with fantastic staff. Anastasia, Orlando, and Fabiano were so kind and attentive. I had my 3 year old daughter with me and she was welcomed by the group, and felt very comfortable. I forgot something in the bus at the end of the tour and the whole team went out of their way to arrange for me to get my belongings back. They could've said it's not possible, but instead, they made it happen! Truly grateful to the staff and this tour was one of my favorite activities in our 10-day trip to Italy. Would book with them again, and highly recommend them!

Super good experience in Tuscany "express". We recommend it to all types of travelers who do not have much time to visit Tuscany, since in 12h you get the best. The wine tasting was also great (although we don't understand much about it).

We loved the Tour, it gives you enough time to get an idea of what the towns are like. The guide Carmen is super nice and always attentive to everyone. We recommend it 100% Ana Belén

The sights were amazing and Lorenzo was a fantastic guide.