Things to do in Monteriggioni

Our most recommended things to do in Monteriggioni

Siena, San Gimignano and Chianti with Wine Tasting and Lunch

1. Siena, San Gimignano and Chianti with Wine Tasting and Lunch

Along the way that will lead you to Siena, stop at San Gimignano, a small and world-famous walled town located on a hilltop, which remained intact through the centuries. It is renowned for its tall towers, wonderful frescoes and many other valuable works of art.  Here, be led to the heart of the historical center, where you will have free time to explore. Following San Gimignano, stop at the charming historical hamlet of Monteriggioni, an amazing medieval village enclosed by its famous walls, which have remained standing to this day.  Enjoy some free time to visit this village. Then, crossing the gently rolling Chianti hills, arrive at a small and typical winery where you will taste 4 fantastic wines and sample balsamic vinegar and locally produced delicacies. Upon arrival in Siena, after free time for lunch, meet your local guide. Take a comprehensive guided tour of the historic center, starting from its most beautiful square, Piazza del Campo.  Walk along the narrow medieval streets of the city, flanked by splendid palaces and historic shops, until you reach the Museum and Oratory of a Contrada (when open), where you can experience the atmosphere of the authentic and most intimate soul of the town. The “Contrade” (districts into which the city is divided) are the real core of local social life, where inhabitants of each district compete with each other, as they devote themselves to the preparation of the famous Palio horse-race.  The Museum of a ”Contrada”, as well as its Oratory, is therefore the heart of the district. It is an intimate and secret place containing historical documents and wonderful relics of the famous Palio, as well as magnificent works of art which are normally not disclosed to the public.  If you wish, your tour can include a guided visit inside the famous Siena Cathedral, built in the 12th century, to discover the beauty of its treasures and works of art.

Florence: Siena, San Gimignano, & Monteriggioni Day Tour

2. Florence: Siena, San Gimignano, & Monteriggioni Day Tour

Explore the heart of beautiful Tuscany on a full-day tour of the towns of San Gimignano and Siena, then discover the bucolic wine region of Chianti. Depart from Florence by an air-conditioned bus to your first stop, the UNESCO World Heritage Site of San Gimignano. Discover one of the most splendid examples of an Italian medieval town. Distinguished by its famous towering skyline, San Gimignano stands along the Via Francigena on the hills of the Upper Val D’Elsa. Get acquainted with the Tuscan environment with the town’s Vernaccia di San Gimignano wine, saffron, and Santa Fina pottery. Enjoy some free time to stroll through the town on your own and see its beautiful squares, architecture, churches, and side streets. Afterward, head out to a unique location in the Chianti countryside to enjoy a wine tasting. Once you hop off the bus, be guided around a splendid winery. Get introduced to the estate's fascinating history and background. Head inside the cellars to learn the secrets of Chianti winemaking together with the local host. Then enjoy a delicious wine tasting of Chianti Classico. Continue to Siena for a guided tour of its enchanting architectural styles, including the Cathedral (exterior only) and Palazzo Comunale (Municipal Building, exterior only) in Piazza del Campo. The famous shell-shaped square provides the stage for the thrilling Palio horse race, run twice every summer.

From Florence: Chianti Half-Day Afternoon Tour

3. From Florence: Chianti Half-Day Afternoon Tour

Discover the Tuscan wine region of Chianti on a scenic guided tour by van from Florence. Visit a local wine estate, tasting its wines and local produce. Immerse yourself in the surrounding picturesque landscape, with a visit to a medieval village in the region. Visit a charming Chianti wine estate, enjoy a guided tour of its wine cellars, and gain an insight into the various stages of wine production.  You know the typical cypress avenue printed on every postcard in any gift store, right? Well yes, you will get to walk on one of these avenues and take memorable photos of authentic Tuscany. Visit a winery that not only offers a tasting that even true connoisseurs will enjoy with great pleasure, paired with samples of sliced cold meats, bruschetta, and salami, but you will also get to enjoy the wonderful surrounding landscape, immersed in an enchanting and welcoming atmosphere.  Visit a real Medieval village in Chianti hills, enjoy some free time to stroll out, and breathe in the local atmosphere. You'll also have the opportunity to buy wine, olive oil, balsamic vinegar, cheese, and herbs to take home.

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

4. 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 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. Visit San Gimignano, 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. Afterwards, stop at a winery for a lunch of salami, cheese, and other local products, accompanied by Chianti tasting.  Discover 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. Finally, enter 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.

From Florence: Siena, San Gimignano & Monteriggioni Tour

6. From Florence: Siena, San Gimignano & Monteriggioni Tour

Experience the charm of Tuscany on a day trip to Siena, San Gimignano, and Monteriggioni from Florence. Try a variety of Chianti wines paired with snacks and admire the picturesque Tuscan hills. Cross the beautiful Chianti hills as you ride south from Florence in an air-conditioned GT bus. Arrive at San Gimignano, a medieval town declared a World Heritage Site by UNESCO. Take time to wind your way through the narrow streets and admire the landscape. Make the second stop at Siena. Explore the Piazza del Campo, famous for the Palio Horse Race and for its splendid examples of Gothic civic architecture. You can also visit the magnificent Palazzo Pubblico. Finally, visit Monteriggioni and its intact medieval city walls. Then, head to the Chianti area and enjoy postcard-perfect landscapes. Conclude your day at a famous wine estate and taste fine Chianti red wine along with homemade snacks.

From Florence: Siena and Chianti Wine Tour

7. From Florence: Siena and Chianti Wine Tour

Escape bustling Florence and discover the regional wines of Siena, Monteriggioni, and Greve in Chianti, with a guided bus tour. Taste test Chianti Classico and extra virgin olive oil, learn about the winemaking process with a winery tour, and marvel at the historic city walls of Monteriggioni.  Enjoy a bus ride from Florence to Siena, marveling at the picturesque countryside and surrounding medieval villages. Tour a winery, taste test a glass of wine, and sample virgin olive oil. Pass through the streets of San Gimignano and Monteriggioni before returning to Florence.

Full-Day Excursion to Siena, San Gimignano & Chianti

8. Full-Day Excursion to Siena, San Gimignano & Chianti

Enjoy a full-day excursion by minivan to see the beautiful Chianti area and to visit the cities of Siena and San Gimignano.  Depart at 9:00 AM from Piazza Cavalleggeri, the meeting point located in the city center of Florence. Stop at Piazzale Michelangelo for few minutes to see the splendid panorama and then in one hour you will arrive in Siena. Take a guided tour of the city center, including Piazza del Campo and the Cathedral. There is free time to walk by yourself in the narrow and ancient streets.  Then leave Siena to arrive in Monteriggioni, an old Medieval little village. After a short stop, continue to San Gimignano where you will have free time to explore the city center on your own. San Gimignano is famous for its towers, vernaccia wine and its characteristic craft articles.

San Gimignano and Volterra: Day Tour from Siena

9. 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.

From Florence: Chianti, Montalcino & Montepulciano - Minivan

10. From Florence: Chianti, Montalcino & Montepulciano - Minivan

Enter the heart of Tuscany and discover medieval villages, ancient farming traditions, delicious local food and unforgettable landscapes. Driving past hills dotted with old vineyards and olive groves, we will reach the town of Castellina, visiting its historic square flanked by open galleries and wandering through its narrow streets. Just outside the village, in one of the area’s best-known vineyards, you will be guided through a short tasting of different wines of the Chianti area, as well as locally produced foods including extra virgin olive oil on Tuscan bread and lavender honey. Continuing along a scenic road we will pass the medieval village of Monteriggioni, as well as the unmistakable clay landscape of the Crete Senesi. From here we will pass along green rolling hills home with ancient villages along the route of 'Via Francigena'. After stopping at a local farm, you will be served a guided lunch-tasting of the renowned Rosso di Montalcino, Brunello and Supertuscan wines, as well as a selection of authentic products of the territory and a delicious homemade fruit pie. We will then visit local wine cellars, and take some free time to enjoy the beautiful surroundings. From there we will make a stop in the medieval village of Montalcino, and visit an imposing 14th century fortress that offers one of the most beautiful views onto Val d'Orcia. Finally, after another short drive, we will reach Montepulciano, perched high above the Val D'Orcia and Val di Chiana. Take some time to explore this town, renowned for its fine wine and elegant squares, before a visit to one of the many wine-cellars of the old town.

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What people are saying about Monteriggioni

Overall rating

4.4 / 5

based on 5,996 reviews

Hello! The trip was wonderful! Our guide Sandro was attentive, cheerful and gave us a lot of information along the route. The chosen itinerary and the proposed objectives are very interesting, and the wine tasting was a unique experience. Leonardo, our coach driver very nice, attentive and very professional. Many thanks to the whole team!

This was definitely one of the top highlights of the trip. Jon was a wonderful and knowledgeable guide, and everything was perfectly planned out. We had ample time in each place and at the winery to see everything we needed to see.

Thank you to Marta and Lido for making our tour entertaining, informative, and comfortable. Recommendations for wine, gelato, and boar were spot on and much appreciated.

Fabio was a wonderful guide and very accommodating. The wine tasting and lunch was very good and would definitely go back.

Great trip, especially Siena and local guide there.