Things to do in
Monteriggioni

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Our most recommended things to do in Monteriggioni

S. Gimignano, Siena, Chianti: Escorted Tour, Lunch & Tasting

1. S. Gimignano, Siena, Chianti: Escorted Tour, Lunch & 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, stop at the charming historical hamlet of Monteriggioni, an amazing small medieval village enclosed by its famous walls, which remained standing to this day. Enjoy some free time to visit this place. Afterwards, you will cross the gently Chianti rolling hills, arrive at a small and typical winery. Taste 4 fantastic wines, then sample balsamic vinegar and other locally produced zero food miles products, to end this memorable experience in the heart of Tuscany. 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, a UNESCO World Natural and Cultural Heritage Site. 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.

Siena: Half-day Guided Hike to Monteriggioni

3. 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.

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

4. 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

5. 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.

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.

San Gimignano and Volterra: Day Tour from Siena

7. 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.

Chianti and Castles Tour From San Gimignano

8. Chianti and Castles Tour From San Gimignano

Experience the region of Chianti and immerse yourself in picturesque Tuscan scenery on this guided, multi-stop trip from San Gimignano. Visit ancient churches, medieval castles, and small villages where the rhythms of traditional life remain unaltered. Stop at 2 wineries for tours and tastings. Explore the home of one of the most famous wines in the world, with its beautiful ruby-red color and characteristic violet-scented bouquet: Chianti. This wine results from a blend of Sangiovese, Canaiolo, Merlot, and Cabernet Sauvignon grapes. Get picked up directly from your accommodation in San Gimignano, then set out to discover the breathtaking landscapes that have cradled the Chianti vineyards for centuries, presenting you with a harmony of colors that can only be found in this region. After some sightseeing, the tour continues with a visit to a charming wine estate. Here, you'll have the chance to see the area close to the famous Castle of Brolio and you'll take part in a guided tour of the castle gardens. When the tour of the garden ends, enjoy a tasting of two different wines. During this tour, you'll see the characteristic Castle of Brolio from the outside as well as the inner garden of the castle. Later, move on to another winery in the middle of the Chianti Classico area, where you'll savor a second wine tasting paired with extra virgin olive oil. The tour ends with drop-off back in San Gimignano.

Eroica Trail E-bike Tour, Wine Tasting & Monteriggioni Visit

9. Eroica Trail E-bike Tour, Wine Tasting & Monteriggioni Visit

Discover the lush landscapes of Chianti on a guided e-bike tour along the historic bike racing route, the Eroica trail. Pass by romantic castles and flourishing vineyards as you take in the rolling hills of the Chianti landscape. Start off with a bus ride to Chianti from the Florence city center and get geared up for your e-bike tour with an expert guide. After the energizing e-bike tour through the countryside, stop at a winery to learn all about the production process of the Chianti Classico. End the cellar visit with a light lunch of local delicacies such as salami, pecorino, and bruschetta, paired with four wines from the cellar. Continue to the walled town of Monteriggioni, known for its medieval fortifications and watchtowers which you can explore at your own pace. 

Siena San Gimignano Private Full-Day Tour by Deluxe Car

10. Siena San Gimignano Private Full-Day Tour by Deluxe Car

Explore Tuscany on this tour of quaint towns and cities. After pick-up from your hotel, the tour will make its first stop in Monteriggioni. Here you can explore a medieval walled town built by the Sienese in the early 13th century. The tour continues to Siena where you will discover one of the most beautiful cities of Tuscany. Siena is famous for its annual historic horse-race, the "Palio," and for its Duomo, an art-filled cathedral that features works by Michelangelo and Donatello. Make your final stop in San Gimignano, one of the most charming and picturesque Tuscan hill towns. Medieval towers dominate the landscape of this UNESCO World Heritage town in a manner that is strikingly similar to the skyscrapers of our modern cities. During the day, you will have the option to stop in a local restaurant for lunch.

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What people are saying about Monteriggioni

Overall rating

4.4 / 5

based on 5,090 reviews

The experience was amazing! We took the semi-independent tour option and all of us really enjoyed this tour, loving all the three Tuscan towns we visited. It was well managed by our excellent guides and the bus we travelled in was clean and comfortable. The tour started by visiting Montereggioni, followed by lunch at Siena, afterwards heading to the winery, and ended at San Gimignano (with some excellent gelato at one of the most renowned gelaterias here). The wine tasting experience (which also let us taste some excellent truffle oil and balsamic vinegar) was also really good at the Chianti winery. I would definitely recommend this tour to everyone who wants a glimpse of Tuscany in a day.

Bus driver and guide in the bus were very kind and informative. The lunch was unexpectedly large. 3 course meal with typical plate of cheese, salami, ham, olive oil and salad. This was the highlight. Main course was macaroni Bolognese and a small piece of cake as last course. Vegan and vegetarian is also possible. Then we could taste 4 different wines. So lunch was way better than expected. The trip to San Gimignano and Montereggioni were well timed. Enough to see the highlight. Same for Siena. We didn't book any guide in Siena and that was fine as well. I can definatly recommend this journey.

We really enjoyed the day. It's a really good way to visit 3 beautiful places and have a wine tasting at the same time. We also received a lot of information about the history and culture of the places. I would recommend trying this tour while visiting Florence.

Enjoyed a nice day traveling around. A very big group, but super guides and perfect amount of time in the different locations. Mostly met expectations. The wine tasting was not very interesting, but ok

We did the day trip to Monteriggioni, Siena, San Gimignano & a winery with Renata and Luca. It was super and we’d highly recommend to anyone visiting Tuscany!