Monteriggioni 

Tuscany

 A Timeless Medieval Gem

Monteriggioni is a beautifully preserved medieval town in the heart of Tuscany that seems frozen in time. Perched atop a gently sloping hill, it overlooks the rolling countryside of Siena and offers one of the most historic experiences in the region. The town was founded in the early 13th century by the Republic of Siena as a defensive outpost against Florence, and its circular walls with 14 imposing towers have remained remarkably intact, creating a striking appearance against the Tuscan landscape.

In this Travel guide, we cover all the best things to do in Monteriggioni, how to get here, and where to stay. Best places to eat, and how much time you need here.

 PLAN YOUR TUSCANY ADVENTURE

These are our favorite companies we use when planning a trip, they consistently have the best prices, great customer service, and overall, are better than their competitors.

BOOK YOUR FLIGHT – SKYSCANNER – we always start here and usually always finish here. They price check over 1,200 travel sites to help you find the best prices. You can also try GOING to search prices across a variety of sites.

TRAVEL OPTIONS

CAR RENTAL – We recommend using Discover Cars or Rental Cars when booking a car rental, they work with hundreds of companies worldwide to help you find the best car for your needs.

TRAINS – TRAINLINE – is our favorite, this site is very reliable and easy to use.

BUS – OMIO – this website allows you to book train or bus tickets to travel from city to city the best and cheapest way. FLIXBUS is another terrific website with routes between 20 European countries.

ACCOMMODATIONS

BOOKING.com – is our go to for hotel searches around the world, we find they always have the cheapest rates and offer different payment options. In addition, VRBO is another terrific website for all types of accommodations.

HOSTELWORLD – is great if you’re traveling on a budget, and if you need a cheap place to stay.

SIGHTSEEING TOURS

GET YOUR GUIDE – is our favorite; they have stacks of tours and excursions available in cities all over the world. VIATOR is another great website for all types of tours.

TAKE WALKS – This walking tour company provides inside access to attractions and places you can’t get elsewhere.

TRAVEL INSURANCE

SAFETY WING – is our go to travel medical insurance company, especially for longer trips. You can either purchase a monthly plan or a plan for specific trip dates (i.e. 1-2 week trips). They cover people from all over the world, while outside their home country.

ARC’TERYX – is a go to reliable brand for outdoor adventure and travel, their wide range includes light weight durable, easy to clean travel gear.

                                  Check out our RESOURCE PAGE for more additional planning.

 

Unlike the larger and more tourist-heavy cities of Florence or Siena, Monteriggioni offers an intimate and glimpse into medieval Tuscany. Walking through its narrow streets, you’ll find ancient stone buildings, quaint shops, and a relaxed atmosphere that transports visitors back to the Middle Ages. The town’s small size makes it ideal for a day trip or a peaceful overnight stay, offering a mix of history, nature, and authentic Tuscan cuisine.

With its location, Monteriggioni is an excellent base for exploring Chianti’s vineyards, nearby hill towns, and the rolling landscapes of Val d’Elsa. Whether you’re interested in history, hiking, or simply soaking in Tuscany’s charm, Monteriggioni promises an unforgettable experience

 

Best Things to Do in Monteriggioni

Walk the Medieval Walls & Towers

One of Monteriggioni’s biggest highlights is its 13th-century defensive walls. Walking along the fortified walkway, you’ll enjoy breathtaking panoramic views of the Tuscan countryside, with its vineyards, olive groves, and cypress-lined roads stretching into the horizon. From this vantage point, you can also admire the town’s well-preserved medieval architecture, making it one of the most photogenic spots in Tuscany.

 

Explore Piazza Roma: The Heart of Monteriggioni

At the center of town lies Piazza Roma, the charming main square where you’ll find cozy cafes, artisan shops, and historic buildings. The square’s relaxed ambiance is perfect for people-watching while enjoying an espresso or a glass of local wine. The standout attraction here is the Church of Santa Maria Assunta, a simple yet beautiful Romanesque church that dates back to the town’s founding in 1213.

 

Visit the Monteriggioni Museum of Arms and Armor

For a deeper dive into the town’s military past, the Museo delle Armature (Museum of Arms and Armor) is a must-visit. This small but fascinating museum showcases medieval swords, armor, and weapons, giving visitors insight into the battles fought between Siena and Florence. You can even try on some replica armor, making it a fun stop for history enthusiasts and families alike.

 

Church Santa Maria Assunta

One of the most beautiful attractions in Monteriggioni is the small church of Santa Maria Assunta from the 13th century. It is located in the main square, Piazza Roma, and the facade is still in its original state. The history of the church is closely linked to the history of Monteriggioni because it was built in the same year as the foundation of the castle. The historic church is therefore, along with the imposing defensive wall, the oldest attraction of the village. Only later, at the end of the 18th century, the bell tower was built.

 

 Hike or Cycle the Via Francigena

Monteriggioni sits along the Via Francigena, the ancient pilgrimage route that once connected Canterbury to Rome. Today, it’s a popular trail for hiking and cycling, offering stunning views of the Tuscan countryside. Whether you embark on a short walk to nearby villages or take on a longer trek towards Siena, the route is a fantastic way to experience Tuscany’s natural beauty and rural charm.

 

Discover Nearby Vineyards and Wineries

Tuscany is famous for its world-class wines, and Monteriggioni is no exception. Surrounding the town, you’ll find renowned Chianti wineries where you can tour vineyards, learn about traditional winemaking techniques, and sample Chianti Classico alongside local delicacies. Some excellent nearby wineries include Castello di Monteriggioni, Fattoria Castello di Staggia, and La Rocca di Cispiano.

 

 Attend the Monteriggioni Medieval Festival

If you’re lucky enough to visit in July, don’t miss the Monteriggioni Medieval Festival, one of Tuscany’s most immersive historical events. The town transforms into a lively medieval fair with knights, jesters, musicians, and artisan markets, allowing visitors to step back in time and experience Monteriggioni as it was in the Middle Ages.

 

Where to Stay in Monteriggioni

Though Monteriggioni is small, it offers a range of charming accommodations, from luxury stays in historic castles to rustic farmhouses in the countryside.

Luxury & Boutique Stays

Mid-Range & Farm Stays (Agriturismos)

 

Where to Eat in Monteriggioni

Tuscany is famous for its cuisine, and Monteriggioni offers several excellent dining spots to savor local flavors.

  • Ristorante Il Pozzo – A traditional Tuscan trattoria known for its homemade pasta, Florentine steak, and truffle dishes.
  • Ristorante Da Remo – A family-run gem offering wild boar ragu, fresh pici pasta, and Chianti wine.
  • Bar Dell’Orso – A casual but highly-rated spot known for Tuscan sandwiches, antipasti platters, and local wines.
  • Antico Travaglio – A cozy wine bar and restaurant specializing in local cheeses, cured meats, and homemade desserts.

For dessert, be sure to try cantucci (almond biscotti) dipped in Vin Santo, a classic Tuscan  sweet wine.

 

How much time do you need here.

The town is tiny so a visit  here is very quick.

If you simply want to walk the wall, take a stroll through the town, and visit the museum, an hour to two hours is all you need. If you have more time, you can sit down to lunch or dinner, and even stay the night.

 

How to Get to Monteriggioni

Despite its medieval charm, Monteriggioni is easily accessible from major Tuscan cities.

By Car

The best way to reach Monteriggioni is by car. It’s located just 20 minutes from Siena and 45 minutes from Florence, making it an easy stop on a Tuscan Road trip. Parking is available just outside the city walls, as the town itself is pedestrian-only.

You can compare car rental prices with our favourites Discover cars or Rentalcars.com

By Train

The nearest train station is Castellina Scalo, about 3 km (1.8 miles) from Monteriggioni. From there, you can take a short taxi ride or a scenic walk to the town.

By Bus

There are public buses from Siena (operated by Tiemme) that run regularly to Monteriggioni. The ride takes around 30 minutes and is an affordable option for those without a car.

By Tour

Many visitors choose to explore Monteriggioni as part of a guided tour from Florence, Siena, or San Gimignano. These tours often include wine tastings and visits to multiple Tuscan villages in a single day.

GET YOUR GUIDE TOURS

Monteriggioni may be small in size, but it offers big rewards for travellers seeking history, culture, and breathtaking scenery. Whether you’re wandering its medieval walls, savouring a Tuscan feast, or exploring nearby vineyards, the town provides an authentic and unforgettable slice of Tuscany.

Perfect for a day trip or a tranquil overnight stay, Monteriggioni captures the magic of Italy’s past while offering all the beauty and charm that makes Tuscany so beloved.

MORE PLACES TO VISIT IN TUSCANY

Best Day Trips From Florence

SIENA – The heart of Tuscany

SAN GIMIGANO – Visit the City of Towers

MONTEPULCIANO – A guide to the wine city

LUCCA – The Gem of Tuscany