San Gimignano
Culture & History

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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.

San Gimignano: Torre Grossa and Duomo Tickets

2. 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.

Florence: Gimignano, Siena, Chianti Tour, Lunch & Tasting

3. Florence: Gimignano, Siena, Chianti Tour, Lunch & Tasting

Discover Tuscany on a guided day tour from Florence to the medieval cities of Siena, San Gimignano, and Monteriggioni. Enjoy views of rolling hills and vineyards, with a stop at a Chianti winery for a traditional Tuscan lunch and wine tasting. First arrive in San Gimignano, a tiny medieval town that has remained intact through the centuries. Sitting upon a hilltop, it is famous for its numerous towers, frescoes, and other art treasures. Enjoy more free time to discover this fascinating city on your own. Next, visit the charming historical hamlet of Monteriggioni, a medieval village enclosed by its famous walls, which remained standing to this day. Afterward, you will cross the Chianti rolling hills and then arrive at a small and typical winery. There, taste 4 wines, and sample balsamic vinegar and other locally produced products. Your final stop is in Siena, where you will have free time to walk along the narrow medieval streets, admiring the splendid palaces, the Cathedral, Libreria Piccolomini, and the famous shell-shaped Piazza del Campo.

From San Gimignano: Chianti Half-Day Vespa Tour with Lunch

4. From San Gimignano: Chianti Half-Day Vespa Tour with Lunch

Start your experience at 11:00 AM and explore the scenic hills of the Chianti region where some of the most famous Tuscan wines are produced. Ride through the beautiful fields of vines, cypresses, and Tuscan rural houses. Enjoy plenty of stops for beautiful photo opportunities throughout your experience.  Stop at a local winery where the kind owners will escort you around their property before serving an authentic Tuscan meal, followed by wine and olive oil tasting. Hop on your scooter once again and follow your guide through the final part of the scenic ride, arriving back at the meeting point at approximately 3:30 PM.

From Florence: Tuscany Wine Tasting Full-Day Trip

5. From Florence: Tuscany Wine Tasting Full-Day Trip

Join this fun day trip to the Chianti countryside by van. Visit two local wineries and taste their flavorful wines, as well as local produce samples. Walk through the streets of San Gimignano at your own pace, discovering this charming town first-hand. Head straight to a wine tasting school to taste 4 different types of wines, a 30-year-old balsamic vinegar, and truffle extra virgin olive oil. Learn how to recognize the different flavors and develop your taste buds together with a wine producer. Move onto a local winery facing the famous towers of San Gimignano. Let the winemakers guide you through the vineyards and the cellars and share the secrets of wine and oil production. At this winery, take the opportunity to buy their local products and wine at a convenient cost to bring back home or to ship to friends and family. In the afternoon, enjoy visiting and spending time wandering through the narrow streets of San Gimignano at your own pace. Shop 'til you drop and enjoy gelato from the world-champion ice-cream making gelateria. Your departure from San Gimignano is at 3:45 PM with an estimated travel time of 1 hour and 10 minutes. You'll arrive back in Florence at about 5 PM.

San Gimignano and Volterra: Day Tour from Siena

6. 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.

San Gimignano: Private Organic Winery Tour & Tasting

7. 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.

From Siena: San Gimignano, Montalcino & Wine Tasting

8. From Siena: San Gimignano, Montalcino & Wine Tasting

The first part of your full-day tour begins with a visit to the walled medieval town of San Gimignano, the City of Fine Towers. Armed with helpful information from your tour escort you’ll have free time to explore the town’s historical center and browse its artisan shops. San Gimignano is also the birthplace of Vernaccia, a white wine produced exclusively in the area. The wine is noted for its high quality and for being the first Italian DOCG wine. The tour continues on to Monteriggioni, the ancient crown-shaped fortress that appeared on Italy’s old 100-Lire currency. The 13th-century walls feature 14 towers that Dante likened to the giants in his Inferno. Afterwards, you’ll stop at a winery for a lunch of salami, cheese, and other local products, accompanied by a tasting of Chianti wines. Visit Val d’Orcia, another Tuscan jewel and a UNESCO World Heritage Site. Continue on to Montalcino, perched on a hill overlooking 1,500 hectares of Brunello vineyards that have contributed to the area’s international reputation. The final stop of the day will be a local wine cellar, where you’ll have a chance to taste the renowned Brunello of Montalcino, rated among the finest Italian DOCG wines. Sample other typical local products as well.

Florence: San Gimignano & Volterra Day Trip with Food & Wine

9. Florence: San Gimignano & Volterra Day Trip with Food & Wine

See the Tuscan gems of San Gimignano and Volterra on a day trip from Florence. Admire the fascinating Tuscan landscape with its rolling hills on the way. Top off your trip with a stop at a scenic winery to enjoy the sunset. Meet your guide in Florence and hop on a comfortable minivan to reach San Gimignano. Get a brief introduction about the city's history and its countless towers. Savor a delicious wine tasting session with light snacks. Stop at a popular gelato shop, winner of the world gelato championship, and order some for yourself from this master ice cream maker. After a guided walking tour, enjoy some free time to shop around the boutiques of the city center. Visit a local winery for a mouth-watering lunch in a unique venue offering spectacular views. Then, proceed to Volterra to enjoy another guided walking tour. Visit local monuments and iconic attractions. Have the chance to see a Tuscan jewelry store and an Etruscan museum. On your way back to Florence, stop at another winery to enjoy the sunset over another wine tasting.

Chianti and San Gimignano Sunset Tour from Siena

10. Chianti and San Gimignano Sunset Tour from Siena

Explore the notable wine region of Chianti on a full-day sightseeing and wine tasting tour from Siena. Travel in a small group of no more than 8 people, and enjoy comfortable transfers by air-conditioned vehicle. Depart Siena in the early afternoon, and drive past the vineyards of the Chianti wine lands. See dense forests of oak wood and cypress trees, neat rows of vineyards, and landscapes shaped into works of art by the combined forces of nature and mankind. Go to a Chianti wine estate to tour the grounds and wine cellars. Learn the winemaking process before sitting down to a tasting of Chianti Classico wines and olive oil. Next, descend to the medieval fortress of Monteriggioni, and marvel at its intact ring of walls and turrets. Built in the 13th century, Monteriggioni was mentioned in Dante’s “Divine Comedy.” As the sun begins to set, travel to the legendary village of San Gimignano to enjoy the romantic town after the daytime crowds have departed. Admire the medieval towers at a leisurely pace, and enjoy some free time to visit the cathedral or Civic Museum. Shop for souvenirs in the many leather and hand painted pottery stores. Sample the local produce at food shops and wine bars. Depart San Gimignano for a Tuscan dinner at an organic farm in the countryside. Taste the wines of San Gimignano, such as the notable Chianti red, Vernaccia. Weather permitting, dinner will be served on a terrace overlooking the cultivated fields and skyline of San Gimignano. Watch the sunset as you dine, before your return transfer to Siena.

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What people are saying about San Gimignano

Overall rating

4.5 / 5

based on 3,949 reviews

This tour was the perfect way to see the Tuscan country side in one day! It’s a long day with a lot of walking but you see so many different things in a short time. Our tour guide was very helpful when needed but also let us do our own things. The winery was amazing and would have loved to spend more time there. If you are looking to get really deep into each city and spend a lot of time looking around this tour probably isn’t for you. We had about an hour to and hour and a half in each city and lunch at the winery was about an hour as well. Would recommend this to friends or family visiting!

This was the most beautiful day we had during our entire trip to Italy. The itinerary is exceptional and very well thought out and scheduled. The lunch at the farm is an absolute MUST DO, it had beautiful views and exceptional food and wine. They were very accommodating to different diets - vegetarian and vegan. Our guide Alessandro and driver Emiliano were both wonderful and have set the bar very high for guided tours. The bus we were in was comfortable and had great AC which helped as it was a hot day!

Enrica was a great tour guide, lots of knowledge and so friendly. Wish we would have had a little less time in Siena and a little more time at the winery perhaps touring around the grounds, but this was the itinerary and no issues with the tour we went on! You still get to see tons in just one day. Overall enjoyable and would recommend.

Excellent 1-day tour to get to know the main places in Tuscany. Our guide Cristina was an excellent hostess and everything was very well organized.

Erika was an amazing guide through these beautiful cities. We enjoyed our time and discovered Tuscany. 100% recommendable.