Best Things to Do in Montalcino: Experience a Beautiful Town

Montalcino is a hilltop gem in Tuscany, world-famous for its Brunello di Montalcino. Surrounded by rolling vineyards, medieval walls, and sweeping views of the Val d’Orcia, the town is perfect for slowing down, sipping award-winning vintages, and soaking up Tuscan culture. This guide highlights the best things to do in Montalcino, from tasting Rosso di Montalcino and exploring the fortress to scenic countryside drives, olive oil tastings, and hearty local cuisine. For an unforgettable escape, discover how Tuscany wine tours paired with Montalcino’s timeless charm create the ultimate Italian journey.

What are the best things to do in Montalcino?

Explore the imposing Fortress of Montalcino

Kick off your adventure with the mighty Fortress of Montalcino, a 14th-century stronghold that still dominates the skyline. From its ramparts, you’ll soak in sweeping views of Brunello vineyards, rolling Tuscan hills, and the winding roads of the Val d’Orcia. Step inside and you’ll find Enoteca La Fortezza, where sipping a glass of Brunello on ancient stone walls feels like a moment straight out of history. It’s one of the most unforgettable things to do in Montalcino, a perfect blend of wine, views, and medieval magic.

Walk around the charming historic center

Montalcino’s old town is pure Tuscan charm. Picture yourself strolling cobblestone lanes that twist past little wine bars, artisan shops, and balconies bursting with flowers. The heart of it all, Piazza del Popolo, buzzes with cafés perfect for a quick espresso or a long glass of vino. Don’t miss the medieval clock tower keeping watch over the rooftops, it feels like a scene straight out of a storybook. Around every corner, there’s another view, another sip, another reason to linger just a little longer.

Set your sights on the Bell Tower of Sant’Agostino

Keep your eyes up — the bell tower of Sant’Agostino pops into view from almost anywhere in town, and it’s as photogenic as Montalcino gets. Right next to it, the church opens its doors to golden altars, Gothic arches, and centuries of stories hidden in the art. It’s a quick stop that adds a touch of culture and history to your wanderings, and easily one of the most charming things to do in Montalcino, especially if you’re hunting for that perfect “I’m in Tuscany” snapshot.

Shop for local products in boutique wine shops

Step into Montalcino’s little wine shops and it’s like walking into Tuscan heaven. Shelves are lined with Brunello and Rosso di Montalcino, but you’ll also spot silky olive oils, handmade pasta, and even wild boar salami begging to be packed in your bag. The shopkeepers know their stuff and love sharing tips on local vintages, sometimes even pointing you to tastings happening nearby. It’s the perfect mix of shopping, snacking, and sipping, with plenty of “one for them, one for me” moments along the way.

Explore Palazzo dei Priori in Piazza del Popolo

Piazza del Popolo is where Montalcino comes alive, and Palazzo dei Priori is its proud centerpiece. The tower rises above the cafés and wine bars, giving the square a touch of grandeur while life unfolds at ground level. Sit on the steps with a coffee, watch locals crossing the piazza, and let the hum of conversation bounce off the medieval walls. Palazzo dei Priori isn’t just a monument, it’s the stage where Montalcino’s everyday charm plays out.

Best Things to Do Around Montalcino

Taste history at a female-run Brunello Cellar

Step into an immersive wine tasting that tells a story, this cellar has been family-owned for generations, passing from mother to daughter, and is proud to be Italy’s first all-female staffed winery. Explore frescoed walls, ancient barrels, and organic vineyards, all while learning about the history of Montalcino and the art of Brunello wine. Cap it off with a tasting of rosso and Brunello accompanied by panoramic views, golden light, and stories that make every sip feel like a celebration.

Camigliano sits quietly among the hills of Montalcino, a castle-village that feels frozen in time, yet alive in flavor. The fortified manor, whose walls date back to the 13th century, holds echoes of medieval life, noble families, and rural traditions that shaped this corner of Tuscany. Here, you’ll wander through vineyards, sink into tastings of bold, aged Brunello, pair your glass with local cheese, and maybe even try your hand at creating your own IGT.

Escape to the surrounding countryside and visit Pienza

Pienza, 14 miles from Montalcino, makes for a dreamy half-day escape through the rolling Val d’Orcia. This Renaissance gem is famous for its pecorino cheese and picture-perfect streets that seem designed for slow wandering. Stroll past courtyards, peek into gourmet shops, and let the sweeping valley views remind you why Tuscany feels timeless. You’ll head back with both your heart and your stomach full.

Don’t miss our guide to the best things to do in Pienza!

Sip among centuries

Nestled in tranquil countryside, this storied estate offers more than just wine, it blends deep history, sweeping views, and world-class tastings into one unforgettable experience. Housed in an ancient fortress dating back to 1100, this place was one of the first four estates to produce Brunello di Montalcino. You’ll wander through organic vineyards, learn how art and tradition shape every bottle at Frescobaldi, and sample tastings that range from casual with Tuscan snacks to full three-course lunches.

Wander to Montepulciano

About 45 minutes from Montalcino, Montepulciano is a Renaissance hilltop town that pairs stunning architecture with world-class wine. Famous for its Vino Nobile, this is the perfect stop to explore Montepulciano wineries and taste how Tuscany’s reds differ from Brunello. Many cellars are hidden beneath the town itself, where vaulted caves make every sip feel like a step back in time. Between wine tastings, fortified walls, and trattorias serving rustic plates, Montepulciano blends culture, cuisine, and heritage into one irresistible experience.

For inspiration on planning your visit, check out our guide to the best things to do in Montepulciano.

Drive to Siena

Less than an hour from Montalcino, the Gothic city of Siena is a must for history lovers and wine enthusiasts. Famous for its medieval walls and the fan-shaped Piazza del Campo, Siena also boasts a thriving wine culture that perfectly rounds out a Tuscan getaway. Duck into cozy enotecas, where tasting Brunello, Chianti, and Rosso di Montalcino feels like slipping into the city’s soul. Between its architecture, cuisine, and lively streets, Siena delivers a full Tuscan experience worth every mile. If you’re looking for cultural highlights, check our guide to the best things to do in Siena, Italy.

If you love wine, nothing beats joining one of the unforgettable Siena wine tours that showcase the region’s finest bottles.

Good to know before visiting Montalcino