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Day trips from San Gimignano

Our most recommended San Gimignano Day Trips From

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, 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.

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 Siena: San Gimignano, Montalcino & Wine Tasting

5. 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

6. 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 Florence: Tuscany Day Trip with a Private Chauffeur

7. 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.

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: 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.

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

10. 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.

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What people are saying about San Gimignano

Overall rating

4.5 / 5

based on 4,503 reviews

Our tour guide Sara was lovely and very knowledgeable about the history of Tuscany. Bravo Sara thank you to our patient driver Gaspare. The tour was jam-packed but we got to visit Siena, San Gimignano and Pisa, ss well as a winery. It was hot and exhausting, but a fun day!! Wear comfortable shoes because you will be walking a lot!!

Very nice tour to the main sites of the beautiful Tuscany. Both Siena, the wine tasting, and Pisa was great. It was a very professional setup Both the driver and the guide was doing excellent jobs. Be aware that due to large scope the it is a full day tour with fairly short time per location.

I usually do not purchase tours and hesitated to do so. However, this tour was amazing! It was well worth it and we got to see places we would have not seen otherwise. The timing at each places were great and the lunch experience was so much fun.

Guides were very knowledgeable and helpful. Really enjoyed the free time with recommendations of places to go. The lunch at the vineyard was really good and I felt it was worth the money!

Fantastic tour guide, lovely food and amazing scenery.