A Guide to Montalcino: Tuscany’s Top Wine Town

Written by Rem Malloy, since 1995 Rem has been guiding and designing trips to Italy and all of Western Europe and is considered an expert in his field for over 30 years.

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An enchanting little utopia rested atop a hill in the province of Siena, Montalcino is a fantastic destination for those looking to sample some of the world-renowned red wine produced in Tuscany. Picture a delightful little town that is full of idyllic cobblestone streets, breathtaking views over the surrounding valley, a captivating medieval fortress and, of course, an exemplary wine scene.  

One of the best towns in Italy for wine connoisseurs, Montalcino is the celebrated birthplace of Brunello di Montalcino – a world-renowned red wine known for its flavors and notes of coffee. Having played a huge role in making the town what it is today, visitors can enjoy plenty of opportunities to sample the famous wine variety at numerous nearby vineyards and wineries.

But Montalcino isn’t just a hot spot for wine lovers. From archery competitions to world-class wineries, there is so much more to this remarkable Tuscan town! 

If you’re already falling for Montalcino’s charm but would like to hear more before planning a trip, we’ve gathered together some key information to help you plan the most unforgettable visit.

History of Montalcino

Inhabited since pre-Roman times, Montalcino is a little town with a fascinating history. As well as producing wine for over a millennium, this place is home to a magical 14th-century fortress, an ancient Basilica, the spectacular tower of San Giovanni and an idyllic Romanesque chapel.

Sitting at a strategic point along the road to Rome, Montalcino played a crucial defensive role back in the day, acting as a stronghold for the nearby city of Siena. In fact, the town’s beautiful fortress was built to protect the Siena republic’s southernmost border.

The monument went on to become a symbol of the town’s pride after protecting hundreds of refugees who fled here during the attack of the Florentines. The town managed to fight off attacks for four years and even declared the second republic of Siena to have been repaired here before finally falling under the rule of the Florentines until the unification of Italy in 1861.

How To Get To Montalcino

Just 50km south of Siena, Montalcino is a fantastic place to stop off for a taste of classic Italian charm. There are several options for getting to this little town.


The nearest airport to Montalcino is Perugia San Francesco d’Assisi Airport in Perugia. To travel to the town, all you need to do is hop on a bus or taxi from the airport. 

It only takes about an hour and a half to drive to the town from here, and you will be able to take in magical views of the gorgeous Tuscan landscapes on the way. Alternatively, you can opt to take a public bus which will take longer but is a better option for budget travelers.

By Train

If you are hoping to reach Montalcino on a railway adventure, there are around 10 trains each day running from Siena to the nearby station of Buonconvento. Taking the Grosseto line, this part of the journey takes around 25 minutes.

Upon arriving at Buonconvento, you will then have to jump on a bus that will take you to Montalcino. Fortunately, the bus timetable tends to coincide with the train arrivals, so you won’t have to wait for too long.

By Bus

If you want to stick to bussing it the whole way to Montalcino, around 12 buses a day set off from Siena to the town on a journey that takes about two hours. While some of the buses take you directly to Montalcino, others require you to change at Buonconvento. So, make sure you check the timetable carefully and plan your journey accordingly.

By Car

You could always find your way to Montalcino by jumping in the driving seat and skirting along the Tuscan roads in a rental car. Altogether, the drive from Siena to Montalcino is 41km and should take just under an hour.

The Best Things to Do in Montalcino

There are plenty of things to do in this beautiful town, from visiting historical sites to shopping in busy town squares. To make sure you don’t miss out on any key attractions, here are our top 3 things to do in Montalcino. 

Check Out The Piazza del Popolo 

While all of the enchanting little streets of Montalcino are buzzing with quintessential Italian ambience, the atmosphere of the main square, Piazza del Popolo, is particularly special. Over 700 years old, the gothic loggia is a true display of architecture at its finest.

While visiting, be sure to get an up-close look at the town hall’s spectacular clock tower. For those who are feeling a little adventurous, you’ll have the opportunity to climb to the top of the magnificent building, from which you will be treated to spectacular panoramic vistas of the Piazza del Popolo and the bustling streets below. 

Visit La Fortezza

Pay a visit to La Fortezza, the town’s medieval fortress. An important symbol of town pride over the years since the town’s four-year resistance to Florentine rule, the monument is now recognized as one of the best things to see in Montalcino. 

Holding such a special place in the hearts and identities of its townspeople, it comes as no surprise that La Fortezza tends to be at the top of every tourist’s to-do list. What’s more, there are plenty of nearby places to pop in for a wine tasting as well as plenty of open space for the kids to explore. So, if you are traveling as a family, you can have the delight of sampling the local vino while the children make the most of the gorgeous surrounding landscapes.

See The Abbey of Sant’Antimo 

A spectacular former Benedictine monastery, The Abbey of Sant’Antimo lies a mere 10km or 15-minute drive from Montalcino. However, many visitors rave about the fantastic hike from the town to the abbey during which you can take in fantastic views ofthe dazzling Tuscan landscapes and catch a tan.

However you choose to get the abbey, the Romanesque architecture is set to blow you away. Constructed from travertine stone, the marvelous building is nestled in the most idyllic of settings; set amidst secular olive groves and peaceful wheat fields in what creates the most peaceful of surroundings.

Festivals and Events in Montalcino

Montalcino plays host to plenty of festivals during the year, so if you are not sure when to visit Tuscany, it might be worth booking your vacation with these exciting events in mind! We have listed a few below that might pique your interest.

February – Benvenuto Brunello 

Calling all wine enthusiasts, the Benvenuto Brunello is the event in Montalcino you should plan to experience! Every February, everyone gathers in the town center in honor of the new vintage of Brunello di Montalcino being launched for public consumption.

Expect the atmosphere to be buzzing with excitement as journalists, bloggers, sommeliers, influencers and – of course –  the general public, gather around in celebration of the great times (and great wine) to come. 

August – Torneo d’Apertura delle Cacce

A bit of a warm-up event for the Sagra del Tordo, the Torneo d’Apertura delle Cacce (or the Opening of the Hunting Season) is an important date in the calendar of any Montalcino local. Held in August, the town’s four neighborhoods, Borghetto, Travaglio, Ruga and Pianello, challenge each other to a crossbow competition in front of the fortress. 

Prepare to see the locals dressed to the nines in their medieval gear, parading around the town while donning velvet robes, piebald tights and elaborate bodices. Of course, you’ll also have the opportunity to get involved with folk dancing in front of the main square.

October – Sagra del Tordo

A tradition going back to 1958, the Sagra del Tordo, or ‘The Song Thrush Festival’, takes place every year during the last weekend of October. The celebrations commemorate the moment when hunters and falconers used to return home with their prey, which sometimes came in the form of thrushes, hence the name!

These days, the main event of the festival consists of people from each district slipping into their regional colors for an archery competition. There is also a parade, lots of medieval costumes and a lot of food involved in what is set to be fun for all the family.

Wineries and Vineyards in Montalcino

While Tuscany is known to be one of the best wine regions in Italy to visit, its little town of Montalcino has gained quite a reputation for itself. The world-renowned grape varieties of the town have played a huge role in building its prosperity.

The popularity of the wine has resulted in the town becoming world-famous and recognized as the birthplace of some of the finest red wines from Tuscany. Made only from the Sangiovese grape variety, which can be found almost everywhere in the Montalcino region, this wine is truly exceptional and simply has to be sampled during your visit.

Here’s what you’ve all been waiting for: a run-through of the best wineries and vineyards in Montalcino. Prepare to be impressed, as this little town is home to some of the best wine tasting tours in Tuscany.

Il Palazzone

Owned by the Parsons family, Il Palazzone is a must-visit for any wine lovers. You won’t just be blessed with the opportunity to try some Brunello, but the owners, Marco and Laura, will also be able to tell you all about the wine and its history in what is sure to be a fascinating experience. 

The estate actually has three separate vineyards in different parts of Montalcino, so their Brunello is infused with an exquisite combination of grapes that have been harvested from different terrains. The area that you’ll be exploring lies just 1km from the town center and has a small store on-site where you can purchase a delightful selection of vintages as well as olive oil and grappa.

Casa Raia

An organic winery set just a short walk from the village, Casa Raia has a fascinating history and lots of unique wine varieties that easily make it one of the best vineyards in Montalcino. 

Many years ago, Ludmilla Temertey was searching for a home in Tuscany and stumbled upon these laboring vines. Seeing the potential, Ludmilla took over the land and was able to give it a whole new lease of life as a winemaking business.

These days, the vineyards and winery are run by her daughter and son-in-law who have replenished the grapes and restored them to their former glory. In fact, the couple are now producing a wonderful range of natural wines that you’ll have to try during your visit.

Biondi Santi

If you are a bit of a vintage wine fanatic and prefer the classic varieties, Biondi Santi is where you should head. The winery is known to be home to bottles that date back to 1888, which is the year when the very first editions of Brunello di Montalcino were ever made!

Your guide will lead you through the enchanting landscapes and estate, bestowing you with knowledge of the history of the winery. Bear in mind that, as Biondi Santi is rather prestigious and a bit of a celeb in the wine world, you will definitely need to book your tour in advance.

Pian Dell-Orino

For an understated and relaxed introduction to the history of Brunello di Montalcino, try Pian Dell-Orino, home to bio-dynamic winemaking techniques. The vineyards here house three different types of soil, each connected to a specific geological formation that is able to give their wines such an exceptional flavor.

Expect to be guided through the grounds and blown away by the stunning sight of the 5.5 hectares of vineyard, 3.5 hectares of forest and enchanting olive trees in what is an incredibly bio-diverse landscape.


A dreamy paradise of dazzling medieval architecture and world-famous wines, Montalcino is easily one of the most beautiful towns in Tuscany and a fantastic place to visit during your Italian vacation. Although the exquisite drinks offered might well be enough to draw you in, this remarkable Tuscany town has so much more to offer beyond being home to some of the most highly renowned red wines from the region. 

With spectacular clocks, breathtaking abbeys, a bustling town center and a wide array of fantastic events going on throughout the year, there is certainly something for everyone in this enchanting part of the world.

If you’re hoping to take a trip to Tuscany and visit magical towns such as Montalcino, get in touch with Italy4Real and speak to a member of our team for personalized advice and help planning a bespoke trip.

About the Author

Rem Malloy started Italy4real back in 1995 with his mother, Deborah de Maio.

He specialises in Italian tours as well as customised tours to France, England, Ireland, Germany, Switzerland, Greece and Spain. He was also featured in the Travel Channel show Mysteries at The Museum in 2016.

Rem has family in Italy and his mothers home town is Cava di Terrani, near the Amalfi Coast. The family has a street named after them in Sorrento, Via Luigi de Maio; a relative who was mayor of Sorrento.

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