Montalcino - Where to Stay, Where to Eat, & Where to Taste

Updated: Jan 10

Is there a more idyllic place than Tuscany? Those sun-drenched rolling hills and Tuscan stone villas can make anyone dream of their own “Eat, Pray, Love” moment. But those picture-perfect moments are not the only reason why many flock to this magical place. We can’t forget the most obvious reason…the wine. I had the pleasure of visiting Montalcino (the southern part of Tuscany) in October, and today I’m giving you the inside scoop on where to stay, where to eat, and of course, where to taste.


Where to Stay:

Borgo Canalicchio di Sopra


This one could be up for debate depending on what you’re looking for and what your budget is. We were in-between renting an Airbnb in the city center and staying at a property owned by one of the best wine producers in the area. Staying in the middle of a medieval village close to some of the best bars and restaurants Tuscany has to offer was tempting. Still, we wanted luxury amenities and a view, so we decided to stay at 5-star Borgo Canalicchio di Sopra. They offer 1, 2, and 3 bedroom villas with breakfast included. The spaces are beautifully updated, and absolutely NOTHING beats the view of the gorgeous pool overlooking the rolling hills. Make sure to stroll through the property’s vineyards and set up a cellar tour. These wines must not be missed!


Where to Eat:

Boccon di Vino

Boccon di Vino was hands down the BEST dinner we had in Montalcino. With the Fiorani family still at the helm, Boccon di Vino has been offering the best flavors of Tuscany since 1992. All the bread is made in-house, the pasta is made fresh every day, and many ingredients come directly from within the region. An added bonus is the view! The restaurant sits on a hill and has a gorgeous terrace overlooking the Crete Senesi. Not to worry if you can’t get a seat outside - the indoor area also has floor-to-ceiling windows. Pro tip: align your dinner reservation with the sunset!


Drogheria Franci

Talk about a wine list! As soon as you walk in, you can’t help but be drawn to the medieval wine cellar spanning a full story…and it doesn’t stop there. All the walls are dressed with some of the best sips Tuscany has to offer. The dining experience includes a pre-fixe menu showcasing primarily organic, biodynamic, and sustainable ingredients coming directly from the region. Not sure where to start with the wine list? Try a wine pairing menu!