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San Gimignano

Day trips

Our most recommended San Gimignano Day Trips

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.

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

2. 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 Florence: Tuscany Wine Tasting Full-Day Trip

3. 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 including the renowned black rooster Chianti Classico, Brunello of Montalcino, Super Tuscan wines, along with a 30-year-old balsamic vinegar, and truffle extra virgin olive oil. 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. Enjoy the Vernaccia white wine and a Chianti Colli Senesi D.O.C.G. 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 icecream 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.

From Siena: San Gimignano, Montalcino & Wine Tasting

4. 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.

Chianti and San Gimignano Sunset Tour from Siena

5. 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.

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

6. 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.

Rome: Siena to San Gimignano Tuscan Wine Tour

7. Rome: Siena to San Gimignano Tuscan Wine Tour

Discover the history of medieval Tuscany with a visit to two of the most famous medieval locations in Italy, Siena and San Gimignano. Along the way, you will taste delicious local food and drink and even enjoy lunch at a wine estate. You’ll depart from Rome to visit Siena, one of the best-preserved medieval cities in Europe, distinguished by its ancient brick buildings. The fan-shaped central square, Piazza del Campo, is known throughout the world for the famous Palio, a historical horse race that is still run today.  While exploring such historic sites, try an Italian coffee and taste some of the typical pastries of Siena: the Panpepato, the Panforte, and the Ricciarelli.  From Siena, you will continue to San Gimignano, known as The Town of Fine Towers. You’ll soon see why, with its absolutely unforgettable skyline featuring a dozen well-preserved tower houses. Explore its charming medieval streets and feel like you’ve stepped backward in time.  You’ll then stop for a wine tasting and enjoy local delicacies in a beautiful local winery. From there, it’s a visit to the local estate to learn how the grapes are processed. Finally, you’ll enjoy a fantastic lunch at the estate's restaurant before returning to Rome.

Florence: Chianti Villages, San Gimignano & Wine Roads

8. Florence: Chianti Villages, San Gimignano & Wine Roads

Journey into the heart of the Chianti region along the famous Chiantigiana Road and through a classic Tuscan landscape characterized by gently rolling hills, vineyards, silver olive groves and dotted with quaint villages. Near Greve in Chianti, enjoy a tour of a local winery with wine tasting. Here you have the opportunity to taste and buy organic extra virgin olive oil. En route, stops to get to know the area including the stunning UNESCO World Heritage Site of San Gimignano, famous for its 13 medieval towers which dominate the skyline. At the end of the visit to San Gimignano, enjoy a traditional Italian light lunch with a wine tasting, either in a wine estate or a typical restaurant producing organic wine. Throughout the day, you will travel in a comfortable car or minivan with an English-speaking driver. 

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.

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

10. 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. 

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Frequently asked questions about San Gimignano Day Trips

What are other things to do than Day Trips that are worth visiting in San Gimignano?

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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 4,503 reviews

Sara (guide) and Fabio (driver) were excellent. We never felt lost, even though each stop went by very quickly. Sara kept us engaged to whichever degree we wanted, and read the room to keep our energy up or let us rest. She was extremely kind, informed, and personable. English speakers will be able to communicate with Sara seamlessly! Other travelers: 1) Eat breakfast before you board! Our group was hungry; 2) Bring sunscreen - the Tuscan sun is no joke!; 3) Pack snacks; 4) Come prepared with lots of 1 Euro and 50 cent coins for public restrooms and factor in wait time; 5) You're able to keep items on the bus, so bring a bigger bag to store your souvenirs and a smaller bag to carry with you; 6) You'll have time to nap and relax on the bus, but never longer than 2 hours at at time; 7) You may think you won't have enough time in Pisa, but for real you only need 30 minutes so this is the perfect way to see it; 8) The meeting point at the train station uses "Walkabout" NOT "GetYourGuide."

We really enjoyed this excursion. Manolo was an excellent guide. Very knowledgeable but also just good at keeping the group together and moving along on the itinerary. I enjoyed all of our stops, but I especially liked Siena where the local guide shared a lot of fun details about Siena’s history and their church was absolutely beautiful. We also really enjoyed the winery and lunch - it was worth paying the extra for this part in my opinion! It is a lot of walking, including to the pick up and drop off locations for the buses since they can only get so close to city centers, so be sure to pack comfortable shoes!

This was fantastic. Out of our two week trip in Italy this was up there in terms of our favorite activity for myself and my husband. Our tour leader was Alessandro, who was funny, personable, very informative and kept our large group together and moving seemingly with ease. And our bus driver Nando was fantastic as well! We loved all of the stops and the lunch and wine were delicious plus a very fun time to meet the other travelers. If you are considering booking this, definitely go for it, especially if this is your first time in the area, you’ll have a great time!

The first winery was a hands on tasting experience where you learned a lot and was also accompanied by absolutely delicious meats, cheeses, crackers, oils, etc The second was less of an interactive experience but didn’t need to be with the breathtaking view you get to enjoy. The bonus of being able to walk around San Gimignano was beyond awesome, so surreal to walk around a town with so much history. It was also a huge park that our guide, Julia, was amazing company.

What an amazing trip this was. Special thanks go to Elizabetta (Amazing, Funny, Joyful, and a friendly Tour Guide) and Giancarlo (Super Driver) for making this a memorable trip. Although I experienced so many tours in so many countries, I never wrote a review. However, this is just something special and I confidently can say this is the best tour I’ve ever had. Yes, “ever”.