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Things to do in

Monteriggioni

Our most recommended things to do in Monteriggioni

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

1. 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

2. 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

3. 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: Siena & Chianti Wine Tour

4. From Florence: Siena & 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. Then it's time to tour the streets of San Gimignano and Monteriggioni before returning to Florence.

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

5. 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. 

Full-Day Excursion to Siena, San Gimignano & Chianti

6. 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.

Siena: Half-day Guided Hike to Monteriggioni

7. Siena: Half-day Guided Hike to Monteriggioni

Give your mind a rest from the noise of the crowded towns, follow your expert guide on a pleasant walk along the Via Francigena, an ancient pilgrim route for the first time plotted down by the Arcbishop ‘Sigeric the serious’ of Cantebury on his return from Rome in the 9th century and considered the main artery to Rome throughout the middle ages. This route, that has for centuries been a highway of men and emotions, a spiritual pilgrimage and a wealthy trade route, has been forgotten and almost entirely relegated to history by the modern paved car roads. Only recently the route has been brought back from the grip of modernity and is today enjoyed by many pilgrims and hikers alike. Experience the beauty of the mixture between the Tuscan countryside and the glory of its medieval past, still present in it's wonderfully preserved castles, villages and ruins.  See the Tuscany you would never want to miss before returning home, pass through forests and fields, vineyards and olive groves from Siena to the imposing fortress of Monteriggioni. A medieval walled town located on a natural hillock, built by the Sienese in the thirteenth century as a bastion of defense in their wars against Florence.  Once in Monteriggioni, enjoy a guided tasting of local organic wines before saying goodbye to your guide for the end of the tour. Feel free to explore the village and the surrounding area at your own pace. You will be given a bus ticket to return to Siena.

San Gimignano and Volterra: Day Tour from Siena

8. 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.

Florence: Private Siena, San Gimignano and Chianti Tour

9. Florence: Private Siena, San Gimignano and Chianti Tour

Explore the beauty of Tuscany in this tour from Florence to Siena, Castello di Monteriggioni, Chianti, and San Gimignano. Visit medieval towns and villages, and drive through idyllic vineyards, with the option to stop at an organic farm and winery for lunch. Meet your friendly guide at your accommodation and drive in an air-conditioned minivan to see the distinguished medieval architecture in Siena, like the seashell-shaped Piazza del Campo and Siena Cathedral before enjoying a scenic drive to Castello di Monteriggioni. Enjoy the small, fortified village and take a short stroll after lunch at one of the local restaurants. Travel along the Chianti wine road which is rich with castles and villages with a stop to admire a small medieval village surrounded by endless vineyards. Experience a unique dining setting while taking in an amazing Tuscan panorama with lunch at an organic farm in Castellina, with the lunch option. Journey to historic center of the picturesque medieval town of San Gimignano and see its ancient towers.

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 Greve. Here we will stop to take a look at local handicrafts and typical products of the Chianti region. Feel free to buy a souvenir to remember this charming town. We will carry on to 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.

Other Sightseeing Options in Monteriggioni

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What people are saying about Monteriggioni

Overall rating

4.4 / 5

based on 5,415 reviews

This tour was amazing. The wine was excelent and our guide was very nice and polite. I strongly recommend this activity if you visit the Chianti area. I will come back to do others for sure

A great tour. Good amount of time at each location, excellent lunch. Get Your Guide were really helpful in sorting out a problem for us so that we didn’t miss the trip.

magnificent experience, punctuality, Erika the guide was fantastic she accompanied us without making us miss anything

We loved learning more about the region and spending time in the towns. The lunch and wine tasting were excellent.

Our wine guide was incredibly knowledgeable and super personable! Would book this again.