Monteriggioni Tours

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Picturesque Monteriggioni is the quintessential Tuscan village, encircled by medieval walls and perched on a hilltop above a rolling expanse of olive groves and vineyards. Stroll through its postcard-perfect center of cobblestone piazzas, pretty churches, and Renaissance townhouses and enjoy the authentic atmosphere.

The Basics
The fortified village of Monteriggioni was founded in 1214 and formed the northern bastion of the Republic of Siena’s territory, often finding itself on the front line in the power struggle between Siena and its arch rival, Florence. Originally, the outpost served as a garrison for Siena’s soldiers and the main Piazza Roma was the vegetable garden that kept them fed in times of siege; today there is a scattering of bars, restaurants, and souvenir shops to keep modern invaders happy. The town’s 13th-century walls incorporate 14 well-preserved towers, so iconic that they were mentioned by Tuscan poet Dante Alighieri in The Divine Comedy.

Monteriggioni is a popular stop on day trips to the Chianti region of Tuscany from Florence, Siena, and Pisa that explore the countryside surrounding San Gimignano, Montecatini, and Volterra; full-day sightseeing tours generally include lunch and a wine tasting of local Brunello di Montalcino wine. You can also explore the area on foot by joining a Tuscany hiking tour, or zip down the country lanes on a scooter during a Vespa tour.

Things to Know Before You Go
  • The rolling hills of Chianti comprise one of the most picturesque corners of Italy, so be sure to bring your camera.
  • The town is accessible to wheelchair users, but if your visit is part of a wine tour, wineries may not be. Check in advance.
  • Tours of Monteriggioni and the villages of Tuscany require a fair bit of walking. Choose comfortable shoes and dress for the weather.

How to Get There
By car, take the Firenze-Siena highway and exit at Monteriggioni. Arriving by public transportation involves multiple bus connections, so the most convenient way to visit is by joining a small-group or private tour that includes transportation.

When to Get There
Monteriggioni hosts a Festa Medievale (medieval festival) in late July, one of the most famous medieval pageants in Italy, with music and dancing, feasting and merrymaking. The Chianti countryside is particularly beautiful in spring and fall, when the fields and vineyards are lush and colorful.

Medieval San Gimignano
San Gimignano is another historic Tuscan village known for its unique skyline of soaring towers and charming medieval center. Like Monteriggioni, San Gimignano is a lovely town to explore on foot, popping into the Collegiata church and local shops, and stopping for a gelato on the main square.
Location
Address: Monteriggioni, Tuscany, Italy
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5 Tours & Activities to Experience

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Florence Day Trip to Siena and San Gimignano

Experience two of the most beautiful cities in Tuscany on a private, full-day tour from Florence. See Siena’s impressive cathedral and the grand Piazza del Campo, home to the famous Palio horse race. Marvel at the 13th-century fortress in Monteriggioni on the way to San Gimignano, a charming hilltop village honored as a UNESCO World Heritage site thanks to its remarkably well-preserved glimpse into Middle Ages Italy. Stop wherever and as often as you like on a fully customized tour, and enjoy the full attention of a knowledgeable driver throughout the day.
  • Duration: 9 hours
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$760.13 USD
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  • Duration: 9 hours
From
$760.13 USD

Siena and San Gimignano: Small-Group Tour with Lunch from Florence

Get a taste of the Tuscan countryside on this full-day tour from Florence. Take a guided walking tour of Siena, home to the famous Palio horse race, and explore the medieval hill town of San Gimignano. Midday, visit a family-owned winery for a lunch of seasonal Tuscan delicacies paired with local wines. Tour size is limited to a maximum of 16 people.
  • Duration: 9 hours
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$183.12 USD
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  • Duration: 9 hours
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$183.12 USD

Small-Group San Gimignano and Volterra Day Trip from Siena

Get medieval on this guided tour from Sienna to San Gimignano and Volterra. Head to the marvelously diminutive hilltop town of Monteriggioni and then stop for a while in UNESCO world Heritage-listed San Gimignano with its plethora of medieval towers and commanding views over the Tuscan countryside. Finally, spend some time in an alabaster workshop in Volterra before indulging in a rustic lunch at a Tuscan farm. This small-group tour is limited to just eight people, ensuring plenty of personalized attention from the guide. 
  • Duration: 8 hours
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$161.24 USD
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  • Duration: 8 hours
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$161.24 USD

Half-Day Chianti Afternoon Tour from Pisa

Chianti is one of Italy’s most popular wine regions but exploring the Tuscan hills can be difficult without your own transport. This half-day tour from Pisa includes round-trip shuttle transport, free time for lunch (own expense) in Florence, and an afternoon wine and food tasting tour of the Chianti wine region.
  • Duration: 5 hours
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$74.86 USD
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  • Duration: 5 hours
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$74.86 USD

Tuscany Hiking Tour from Siena Including Wine Tasting

Become a pilgrim of sorts and take a scenic hike on the historic Via Francigena, an old pilgrimage route that stretched from Canterbury in England to Rome. The rural route, about 5 miles (8 km), takes you through villages, vineyards, and some of the most scenic countryside in Tuscany. Best of all, once you get to the village of Monteriggioni, one of the most gorgeous hill towns you’ll ever step foot in, you’ll be rewarded with a wine tasting. At the end, head back to Siena via train.
  • Duration: 4 hours
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$51.83 USD
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  • Duration: 4 hours
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$51.83 USD


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