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!


Alle Logge di Piazza

Unfortunately, they weren’t open when we were there; however, you absolutely cannot visit Montalcino as a wine lover without stopping into Alle Logge. Located next to the Piazza, Alle Loge offers a great wine list, service, and views. It’s an excellent place for lunch or even an aperotivo. They’re known for mouthwatering pici with guanciale and onions, steak tartare, and bruschetta.

Osteria di Porta al Cassero

Are you looking for an authentic home-cooked meal? This is the place! Showcasing a simple menu with typical ingredients, Osteria di Porta al Cassero’s dishes taste like a warm hug from nana. Kick back, relax and let one of the very knowledgeable servers suggest the perfect Brunello to pair with your meal. The vibe is casual and friendly and it's the ideal place to end your day after a full itinerary of wine tasting!

Where to Taste:

Ciacci Piccolomini d’Aragona

Dating back to the 17th century, Ciacci Piccolomini is producing premium wines by the Bianchini family. 55.5 hectares are farmed using organic practices, including my favorite vineyard, “Pianrosso,” used for their Riserva bottlings. The views are to die for as the property is set between Arna hill and the Orcia River with Mount Amiata in the background. Pro tip: make sure to try their estate olive oil!


Sanlorenzo Montalcino

Owner/winemaker Luciano Ciolfi produces what the locals call “the real Montalcino.” Here, I learned and experienced how vintage variation affects Montalcino and the flavors, aromas, and textures we find in our glass. It was also where I experienced my first rosé from the region! It was an incredibly personable experience, and the wines were raw, energetic, and terroir-driven.



Conti Costanti

Visiting Conti Costanti felt other-worldly. I had to pinch myself to make sure I hadn’t pre-maturely ascended into heaven. Making Brunello since 1865, the Costanti family is still very much at the helm of the estate. Their land covers 25 hectares, 12 is under vine, and four is for olive groves. The portfolio includes impressive and expressive Brunello along with Rosso di Montalcino and Grappa.



Canalicchio di Sopra

Even if you don’t stay on the property, booking a tasting appointment here is a must! The cellars were recently renovated, showcasing the estate’s innovative values while keeping tradition. Francesco guided us through a highly comprehensive tasting with a significant focus on terroir. It was fascinating to taste the many expressions of Sangiovese across different microclimates, terrain, and exposures.



Biondi-Santi Tenuta Greppo


We can thank the Biondi Santi family for our beloved Brunello. In fact, Clementine Biondi gained international recognition for Brunello in 1865. The property includes 26 hectares of vines including their very own Sangiovese clone, "BBS11." BBS11 is the only clone ever to be named after a producer. These wines are highly collectable, however during our tasting we had a great conversation about how wine is meant to be enjoyed! Note: reach out to the winery directly for availability.



Enoteca la Fortezza di Montalcino

A must-see tasting room and wine shop (or, should I say, wine fortress) at the top of Montalcino. It was founded in 1980 and is considered one of the oldest wine bars in Montalcino. Fabio Tassi of the famous Tassi wine label manages the shop and offers the best of the region. Places like this are unique because they allow you to taste wines from producers you could not visit during your stay. The best part? Free shipping to the USA with 12 or more bottles of Brunello!



Thank you to our friends at Bravino Wine Club for the incredible hospitality during our stay in Montalcino. To find out how you can receive exclusive Italian wines shipped directly to your home, click here. For specific Italian wines I've been loving all winter long, make sure to check out "10 Italian Reds to Crush on This Winter."

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