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San Gimignano Neighborhood tours

Our most recommended San Gimignano Neighborhood tours

Florence: Pisa, Siena, San Gimignano, and Chianti Experience

1. Florence: Pisa, Siena, San Gimignano, and Chianti Experience

Start in the morning with a tour of Pisa. Have time to admire the cathedral, the baptistery, the monumental cemetery, and the famous Leaning Tower. Then move on to a typical winery in the Chianti Hills on the slopes of San Gimignano. Enjoy a Tuscan lunch accompanied by a local wine tasting. Following lunch discover one of the most beautiful medieval villages of San Gimignano, or the "Medieval Manhattan, where you can explore the maze of cobbled streets, small squares, and many local craft stores. Continue on with a panoramic view of the Chianti countryside before arriving in Siena, where if desired, your professional guide will take you to see the most important squares, from Piazza del Campo to the cathedral, passing through the most beautiful contrade that characterizes this city. At the end of the guided tour, choose to have some free time to enjoy a cup of coffee or a panforte (a typical local cake), and to go shopping. Your return to Florence will have a gorgeous sunset in the backdrop, making for a perfect ending to an unforgettable day spent in Tuscany.

From Florence: Tuscany Day Trip with Lunch at Chianti winery

2. From Florence: Tuscany Day Trip with Lunch at Chianti winery

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: Siena, San Gimignano & Chianti Day Trip with Lunch

3. Florence: Siena, San Gimignano & Chianti Day Trip with Lunch

Hop aboard your minibus at 7:45 AM and drive for around an hour through the Tuscan countryside. Enter the heart of Siena, and start the visit with your guide. Take off through the town's narrow streets and hear stories about Siena as you go. Skip the line to see the interior of the magnificent cathedral, and pass through the shell–shaped Piazza del Campo, where the Palio horse race is held twice a year. After your walking tour, enjoy some free time to enjoy Siena at your own leisure. Move on to San Gimignano, and admire the unique Tuscan landscape as you drive through marvelous scenery surrounded by olive trees, vines and old stone buildings on your way. Stop at a family owned wine estate to relax and enjoy a traditional Tuscan lunch for a taste of country hospitality. After lunch, take an easy drive to San Gimignano to finish your day. Famous for its splendid skyline of tall medieval towers, have free time to explore on your own. Discover the main street full of typical shops, have a look at the Collegiata (main church), or enjoy a gelato. Return to Florence in the late afternoon.

San Gimignano and Volterra: Day Tour from Siena

4. 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. 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.

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

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

Start your experience in the morning 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 in the early afternoon.

San Gimignano: Vernaccia Wine Tasting Experience

6. 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.

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

7. 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. 

San Gimignano: Private Chianti Hills Tuk-Tuk Tour

8. San Gimignano: Private Chianti Hills Tuk-Tuk Tour

You'll depart from the headquarters located in Poggibonsi at 10:45AM, where your wonderful guide will welcome you. From there you will venture then through the panoramic roads of Tuscany and the Chianti hills where you are bound to fall in love with the fields of vines, cypresses, and Tuscan rural houses. Don't forget to bring your camera, as there will be plenty of photo opportunities to capture the eagerly awaited moment and freeze it in time. Your next stop will be to a local winery where the kind owners will take you around their property before serving a wonderful and authentic Tuscan meal complete with a wine and extra virgin olive oil tasting. Following lunch you will hit the rad once again to travel through the iconic Ape Calessino to enjoy the last part of this scenic drive. You will later arrive back to the office at approximately 3:45PM, which will mark the end of your tour.

From Florence: Pasta Cooking Class at San Gimignano Winery

9. From Florence: Pasta Cooking Class at San Gimignano Winery

Upon arrival, you will be greeted by the staff in the welcome center then go for a short walking tour of the historic property. Then you will begin your unique pasta cooking class where you will learn how to make authentic Italian pasta with a seasoned professional in a relaxed and respectful environment.  Here you learn to cut, braise, boil, cook and roast a complete Tuscan meal with great pleasure and fun creating unforgettable dishes in the kitchen. Then enjoy your handmade pasta and enjoy wine, locally sourced meats, fresh products of our vegetable garden and plenty of fresh bread with extra virgin olive oil. Discover the secrets of pasta making and enjoy Tuscan culture and cuisine. 

From Florence: Private Full-Day Jewels of Tuscany Tour

10. From Florence: Private Full-Day Jewels of Tuscany Tour

Be seduced by the eternal charm of Tuscany’s jewels on this 12-hour tour. What are Tuscany’s jewels? The beautiful cities and villages, as well as art and the historical monuments that call this unique region of Italy home. Falling in step with the more ‘human’ way of life in Tuscany, this relaxed tour begins when you want it to. You determine the pick-up time from your centrally-located Florence hotel. You will also enjoy the transportation, which is provided by a private vehicle operated by an English-speaking driver. After pick-up, you will drive through the Tuscan countryside until your first stop, Siena, is reached. Siena is a medieval city known for its artistic treasures, which have been recognized by UNESCO. In Siena you will visit the shell-shaped Piazza del Campo. Here you will find the Palazzo Comunale flanked by the Torre del Mangia. Every year the famous Palio takes place here. You will also have free time to visit the cathedral, built in the Middle Ages and admire the splendid buildings and narrow streets. From Siena, you will enjoy a drive through Chianti territory on your way to Monteriggioni. The drive boasts a panoramic view of the vineyards and olive groves. Monteriggioni is a small 13th-century town which is still surrounded with its original town walls. Here you will take a walk within the restricted perimeter of the walls, which have eleven towers with spectacular views. This is a Tuscan gem that will transport you back in time. Only a short distance away, in a pleasant country estate you will be served a typical Chianti-region lunch. You will also enjoy a guided tasting of Chianti and Vernaccia wines. After lunch you will leave the estates and go to San Gimignano, another beautiful town and UNESCO world heritage site. Famous for its signature medieval town planning, it is called the “Manhattan of the Middle Ages”. On a stroll through the town center you will discover the Piazza della Cisterna, the Dome, the Palazzo del Podestà and the Church of Saint Agostino. Your final stop will be at the famous town of Pisa, which is also a UNESCO world heritage site. In the Piassa dei Miracoli the masterpieces in marble rise from the green lawn, including the famous Leaning Tower of Pisa, the magnificent Baptistery, the stunning Cathedral and the Monumental Graveyard Tuscany is a one-of-a-kind region of boundless natural and cultural beauty. This small, personalized tour is an authentically Tuscan experience.

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What people are saying about San Gimignano

Overall rating

4.5 / 5

based on 10 reviews

Wonderful trip! One of the highlights on our trip to Italy! So much information and history. We loved it! Things to note it is a LOT of walking. We walked the 10 minute walk from our hotel to the train station so that added on but we clocked over 20K steps that day. I would say we are fairly average size Americans, my husband is 5'9, I'm 5'6 the bus was a bit of a tight squeeze with no bathroom. If we had been taller or plus sized it would have been very uncomfortable.

A wonderful experience with a wonderful guide and bus driver! Barbara was very warm, friendly, and helpful and took extra measures to ensure everyone was having a nice time. She is a delightful guide and very knowledgeable! Fiorenzo is a very safe driver and got us everywhere on time with no problems. Definitely recommend!

The tour was conducted by Walkabout. It was one of the most organised tour I had in Italy. Guide Lavinya was excellent. Her knowledge in Tuscany region and passion for tour is excellent. Great experience with Wine testing. Good to know the local history of Florence, Siena , San G and Pisa..I highly recommend this tour

The vans were very comfortable. Our driver was a sweetheart. Plenty of time in each area. We left a couple of areas a little early by our choice because the weather was windy and cold. Our driver came each time we called.

Everything we wanted to visit in Tuscany into one day: Pisa, Sienna and the countryside. Saint Giminagno the most beautiful discovery