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Monteriggioni

Food & gourmet tours

Our most recommended Monteriggioni Food & Gourmet Tours

Chianti and San Gimignano Sunset Tour from Siena

1. 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 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.

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

3. 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 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. 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

5. Chianti and Castles Tour From San Gimignano

Immerse yourself in the picturesque Tuscan scenery on a sightseeing trip to the beautiful region of Chianti. Visit the Castellina in Chianti before enjoying a wine tasting at a winery in the area. The beautiful ruby-red color and the characteristic bouquet with scents of violet are the special features that reveal the identity of one of the most famous wines in the world: Chianti. This wine results from the wise blend of Sangiovese, Canaiolo, Merlot, and Cabernet Sauvignon grapes. On this trip, discover the breathtaking, uncontaminated landscapes that have been cradling the Chianti vineyards for centuries, presenting you with a harmony of colors that can only be found in the hills of this region. The sounds, scents, and flavors of this land will capture your senses through a unique experience. Visit ancient churches, medieval castles, and small villages where the rhythm of life remains unaltered over time. Later, move on to a winery in the middle of the Chianti Classico area, where you’ll have a wine tasting alongside an extra virgin olive oil tasting. The tour will end with a return to Siena.

From Florence: Chianti, Montalcino & Montepulciano - Minivan

6. 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.

From Rome: Siena, Chianti, Wine Tasting and Lunch

7. From Rome: Siena, Chianti, Wine Tasting and Lunch

This tour has been designed to showcase the very best of Tuscany in just one-day and is perfect for travelers who only have a short amount of time. The day begins with departure from Rome at 6:45am on a fast speed train to Florence. Upon arrival in Florence, head to the meeting point sent to your email to meet your guide and set out on your sightseeing adventure. The first stop of the day is the historic city of Siena, which is bursting with rich architectural styles, best showcased at the cathedral and the old palace. After a brief guided walking tour of Siena, enjoy free time to explore on your own. Wander around the quaint streets of this magical town, have a traditional Italian lunch at one of the many cafés, or shop for handmade crafts and souvenirs. Continue the tour to the walled town of Monteriggioni next, which was the filming location of the blockbuster movie, Gladiator. Arrive at the UNESCO World Heritage Listed San Gimignano next, which is the most famous walled medieval town in Tuscany, and nicknamed the ‘Manhattan of Tuscany’ due to its many towers. Armed with tips and recommendations from your guide, head out on your own adventure in the town and visit the sights and attractions that interest you most. Don’t forget to stop by the store of the world-champion gelato maker, and treat yourself to a seriously sweet treat. During the day, ride through the rolling countryside of Chianti and soak up the charming scenic views on the way to an authentic Tuscan winery. Against the backdrop of luscious vineyards and olive groves, enjoy a spectacular lunch with a wine and olive oil tasting session. At the end of a truly unforgettable day, head back to Rome, arriving at approximately 8 PM.

Siena, San Gimignano and Chianti Experience

8. Siena, San Gimignano and Chianti Experience

Explore the essence of Tuscany: Siena, San Gimignano and Monteriggioni are waiting to be discovered. The first step is Siena. Here, be welcomed by a local guide that will lead you through the most typical spots such as Piazza del Campo and Piazza del Duomo, where you can appreciate the authentic medieval atmosphere which makes this town special and unique. After that you will have an hour of free time that you can spend to visit the Duomo, do some shopping or simply enjoy the local deliciousness. Back in the minivan, head to the lovely town of Monteriggioni. Built in 1213, its fame was so big that the great poet Dante Alighieri made a sign to his round enclosure in the Divine Comedy. Here, finally, have lunch in a typical restaurant and have the chance to taste local food and wine. In the afternoon, reach San Gimignano, where you will have free time to discover the town and admire the amazing landscape. The city of beautiful towers, has been nominated as a UNESCO world heritage site as an example of a medieval town. At the end of the visit, come back to Florence in full comfort just in time for the sunset.

From Florence: Private GUIDED tour, Siena & San Gimignano

9. From Florence: Private GUIDED tour, Siena & San Gimignano

• Stop At: Siena, Tuscany. Experience Siena through the expert and knowledgeable lens of a professional tour guide! Siena is one of the most popular and visited places in Tuscany. It is known throughout Italy for its distinguished medieval architecture. Upon arrival, explore with your guide Siena’s rich history and art, through its notable local monuments such as the famous seashell-shaped Piazza del Campo and the outstanding Siena Cathedral. Many local shops fill the historic streets of Siena, a great opportunity for you to taste local food or buy some gifts! Duration: 3 hours • Stop At: Castello di Monteriggioni, Tuscany. Make a lovely stop in the small, fortified village, which is still surrounded by its original medieval walls. Located not far from Siena, Monteriggioni is a great spot for a short walk after lunch at one of the local restaurants. Duration: 2 hours • Pass By: Village of Fonterutoli, Siena. Fonterutoli has been an important village ever since the Roman times. The Via Romea passes here, and is still today traveled by pilgrims from all over the world. Location of the historic Mazzei family since 1435 (for 24 generations), the village of Fonterutoli maintains its medieval appearance intact. Stroll in the village to stretch your legs and take some beautiful photos. Duration: 30 minutes •Stop At: Organic Farm/Winery Tenuta Casanova, Tuscany. (*optional) *OPTIONAL lunch at the Farm or Winery. Have lunch in a wonderful organic farm. While the owner will show you around the property, his wife will prepare a delicious and unforgettable lunch for your private group. The owner will show you to his cellar to admire his Super Tuscans and Chianti Classico wines -Craft Wine- and to the nearby Acetaia, a vinegar cellar, with old vinegar. Afterwards, experience a unique dining setting while taking in an amazing Tuscan panorama. You will taste organic specialties, such as the typical Lasagna with traditional sauces, crostini, local meats and cold cuts, legumes, seasonal vegetables, honey, and cheeses seasoned with an incredible aged balsamic vinegar. Wine will accompany this lunch every step of the way. Each of the four main courses and desserts will be paired with a different and distinctive glass of wine. We will conclude with ice cream and balsamic vinegar or other desserts. (This option will slightly reduce your time to visit the cities of Siena and San Gimignano, and exclude the possibility to visit the fortress of Monteriggioni). Duration: 2 hours •Stop At: Historic Center of San Gimignano, Tuscany. The beautiful stronghold of San Gimignano is one of the most popular tourist attractions in Tuscany. San Gimignano is a treasure of medieval architecture, frozen in time at 1300 AD. Above all, it is famous for its ancient towers, which still stand out from its skyline, earning it the nickname Manhattan of the Middle Ages. This is the last destination of the day, before returning to Florence. Duration: 1h30m

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What people are saying about Monteriggioni

Overall rating

4.3 / 5

based on 4 reviews

Amazing experience !! I loved every moment. High recommend this wine tasting tour. It was more than I expected and very memorable. From beginning to end, everything was just wow. We explored wonderful cities, got to taste some exquisite wines from the Chianti and Montalcino lands - both Chianti and Brunello wines were such a tasteful delight . Above all, Fabio was amazing. Not only is he a man with class, charisma, and great character but he is funny and knowledgeable. He really taught us a lot and took us to wonderful picture sites and gave us tips and places to see for each little village we stopped at. Fabio I hope to see you again one day! From Jessica and Anthony- de Canada

We had a great day. Great driver, great wine tasting and gorgeous villages and scenery, definitely recommend.

Fabio was an great host. Awesome personality that made the tour even more enjoyable.

Fun time. Too much time spent in the wineries we visited.

A fantastic tour and a highlight of our holiday in Siena!