San Gimignano
Nature & Adventure

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Our most recommended San Gimignano Nature & Adventure

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.

S. Gimignano, Siena, Chianti: Escorted Tour, Lunch & Tasting

2. S. Gimignano, Siena, Chianti: Escorted Tour, Lunch & 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, stop at the charming historical hamlet of Monteriggioni, an amazing small medieval village enclosed by its famous walls, which remained standing to this day. Enjoy some free time to visit this place. Afterwards, you will cross the gently Chianti rolling hills, arrive at a small and typical winery. Taste 4 fantastic wines, then sample balsamic vinegar and other locally produced zero food miles products, to end this memorable experience in the heart of Tuscany. 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 Siena: San Gimignano, Montalcino & Wine Tasting

3. 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, a UNESCO World Natural and Cultural Heritage Site. 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.

San Gimignano: Torre Grossa and Duomo Tickets

4. 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.

San Gimignano: Private Organic Winery Tour & Tasting

5. 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 Florence: All inclusive Tuscany Vespa Tour in Chianti

6. from Florence: All inclusive Tuscany Vespa Tour in Chianti

The day starts with pickup from central Florence (see meeting point section) where the group will be taken in an air-conditioned van/coach to the Chianti region. Upon arrival, a local English-speaking guide will share some information on the region before giving a brief safety demonstration and assigning the Vespas.   Start the Vespa ride on the quiet and scenic roads through the rolling hills of the Chianti region where some of the most famous Tuscan wines are produced and fall in love with the fields of vines, cypresses, and Tuscan rural houses. Admirea the skylines of the incredible Medieval villages like Sna Gimignano and listen to the legendary stories that these places hold from your local guide When hunger strikes, the group gathers back together at a local winery to share an authentic Tuscan meal combined with a light wine and olive oil tasting.   After a day full of sightseeing, the group returns to Florence at approximately 5:00 PM.

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

7. 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 San Gimignano: Chianti by E-Bike with Wine Tasting

8. From San Gimignano: Chianti by E-Bike with Wine Tasting

There is no better way than by bicycle to discover the beauty and richness of this part of Italy, sharing in the passion for cycling, art, food and wine. The tour takes place in Tuscany, more specifically, in the magnificent landscapes surrounding Siena. There are, in fact, the most beautiful areas and also the most suitable for a cycling trip through Tuscany. From the seat of your electric bike, you will discover how Tuscany life flow slowly yet incessantly, creating a natural equilibrium among art, culture, and nature. Tuscany is paradise for a cycling tourist, who will be greeted by gently rolling hills embellished with winding dirt roads, curving pathways, vineyards, and shaded country roads. All of these splendors are framed by a surprisingly varied landscape where you will be able to discover abbeys, rural churches and castles. The landscape is characterized by the deep red earth, and alternates between fields of sunflowers and vineyards, and is punctuated by ancient castles and medieval hamlets. Many panoramic views allow you to see all the way to San Gimignano, overlooking forests of beautiful Italian oak and corbezzoli. The tour is crowned with a visit to the splendid medieval for tress of Monteriggioni. 

Florence: Siena, San Gimignano, Chianti, & Pisa with Lunch

9. Florence: Siena, San Gimignano, Chianti, & Pisa with Lunch

Get lost in the beauty of Tuscany with this tour from Florence to Siena, San Gimignano, Chianti, and Pisa. Have some free time to explore San Gimignano, Siena, and Pisa at your own pace.  Meet an assistant that will help you board the comfortable coach. Relax and enjoy the countryside on the drive, or make use of the free onboard Wi-Fi. Drive through Chianti vineyards on the way to Siena. Wander through the pedestrian-friendly heart of this historic hilltop town. Stroll through the medieval brick buildings of Siena with free time to see its central square Piazza del Campo, its Gothic town hall, or its 14th-century Torre del Mangia tower. Continue through the countryside and stop at a wine estate surrounded by lush rolling hills.  Sit down for a traditional Tuscan lunch which is served with a selection of delectable regional wines. Depart for the medieval UNESCO World Heritage town of San Gimignano. Walk through its cobblestone streets and small squares to uncover charming craftsmen’s shops. Pass by hilltop hamlets and churches on the way to Pisa. Admire the Field of Miracles, a green grass area dominated by the dazzling white buildings of the Cathedral. Snap an iconic picture at the Leaning Tower. View an exquisite example of Pisan Romanesque architecture at the Baptistery. return to your meeting point in Florence.

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

10. Florence: Siena, Pisa, and San Gimignano Day Trip with Wine

Boarding your air-conditioned coach in Florence, you will meet your tour leader who will stay with your group for the duration of your day trip. As you journey through the rolling hills, vineyards and olive groves of the Chianti region, they will tell you what to look out for in each new town. Your first stop will be the medieval town of Siena, where the Palio horse race has been held twice a year since the 17th century. When you arrive in Siena you will have free time to explore the red-bricked city and admire the magnificent Duomo di Siena which stands out with its white and greenish-black marble facade. Back aboard your coach, you will spot the iconic tower houses of San Gimignano on the skyline from miles away. This Medieval walled town will be yours to explore, as you wander back in time along the narrow streets, being able to ask your tour leader where to find the best gelato. After enough free time to explore and take pictures, rejoin the group for your complimentary glass of Chianti wine and some nibbles. The coach will then return you to Florence. Hop back on your coach and enjoy a transfer to Pisa. Here you will have free time at the Piazza Dei Miracoli (Square of Miracles) to take pictures in front of the infamous Leaning Tower of Pisa. You will also have time to explore the lesser-known Duomo, a UNESCO World Heritage Site and Baptistery, before your driver returns you to Florence

Frequently asked questions about San Gimignano Nature & Adventure

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Other Sightseeing Options in San Gimignano

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What people are saying about San Gimignano

Overall rating

4.5 / 5

based on 3,969 reviews

I highly recommend the tour for people, which want to see some highlights of Toscany. As I’m not eating mean I was even surprised to have some nice pasta and other dishes which made my stomach happy and Alexandro, he was a guide with a passion, always there when you have some questions

Our guide Ale from Walkabout Florence was amazing! Spent the time to talk to each of us, and was more than happy to answer questions and give us suggestions about the places we went to!

Our guide Sonia was wonderful! If we were to do anther excursion like this, we’d do only 2 towns, 3 seemed too rushed.

It was great, the landscapes, the lunch, the cities visited, everything was very beautiful.

Tour guide was fun and gave us tips for good wine and gelato places to go to! :)