When I was 5-6 years old my family rented a villa in Montalcino, Italy. Montalcino, if you are not familiar, is a small walled medieval town in the heart of the Tuscany Brunello wine region - an absolute paradise for children and adults alike. The villa we rented was smack in the middle of a vineyard and although I was very little, I still have vivid memories of that summer. When I think back to that summer, I can remember running through the vineyards, stomping on grapes, eating fruit right off the trees, playing in the small square in town, and hearing the church bells ring. I also remember how right before the end of the trip, on the first weekend in September, my mom took us to a medieval festival where the city splits into 4 quarters and competes to win the ‘Gold Lance’. They joust, have archery competitions, have a parade in historical costumes, and at the end of the day lots of culinary meet ups. It was paradise!
Fast forward 20+ years to the present and after coming back from a recent trip down memory lane, I had such a fabulous time re-experiencing Montalcino as an adult. This is why I had to promote this destination and write a little travel guide for anyone going so they can make the most out of their stay. Are you ready for it?!
Si Montalcino - this beautiful boutique style villa is the perfect place to stay if you are visiting the region. A less then 5 minute drive to town, the property offers free parking and free breakfast with your stay, a pool, and verandas that look over the Tuscan countryside. Our room was lovely and definitely had some Tuscan charm. The bathroom had been newly renovated in a very clean and modern style. We also had a private terrace where we enjoyed our morning coffee while planning the day’s activities. The staff were very helpful and answered questions to whatever we couldn’t look up using the hotel internet which was one of the best we experienced in Italy. The hotel also has a very friendly, beautiful dog that likes to welcome you back - very quiet and can often be found sunbathing. I highly recommend this place for the location, price, and what it includes. It is well worth every penny. The only thing that I was sad about was that I couldn’t stay longer.
Drogheria Franci (In Montalcino) - One of the best meals of our entire trip. The carbonara here was unbelievable but I was very satisfied with every dish that was served. The chef puts a modern twist on classic Italian dishes and his deep knowledge of the cuisine and inventive new approaches were executed perfectly. The wait staff is very friendly, speaks english and is very helpful and knowledgable about the menu. There is a wine store that is attached/part of the restaurant so they also have a very deep understanding of wineries in the region. Instead of ordering a bottle for our meal, my boyfriend and I asked our waiter to split us a glass with each plate so we could do parings which ended up working out so much better and came to about the same price as a bottle. You definitely have to eat here so make a reservation ahead of time!
Il Pozzo in San Angelo (15mins drive from Montalcino) - Traditional Tuscan cuisine at its finest! This restaurant was recommended to us by many people including the wait staff at Drogheria Franci. This rustic restaurant was super busy (even for when we went on a Sunday evening) and after tasting their food I could tell why. Tucked into a small corner of the little hilltop town of San Angelo, this restaurant offers a variety of fresh pasta dishes, and is famous for their excellent Steak Florentine. Come hungry because you will want to try everything on the menu and I’m positive you won’t be disappointed.
Latta de Luna in La Pienza (20mins drive from Montalcino) - If you are willing to drive a little further away from Montalcino, you have to visit the town of Pienza. This cute Tuscan town is bigger in size then Montalcino but offers the same kind of medieval charm and architecture with more stores to peruse and restaurants to try. When in town, after enjoying the sites I definitely recommend going to Latta de Luna for a bite. Their menu consists of traditional Tuscan cooking and they are known for their suckling pig which we had and was cooked to perfection. Since we went in September they also had some seasonal offerings including a squash soup which I was in heaven over. Definitely a nice little spot to grab a bite if you are willing to make the trip.
Bruno Dalmazio Wine Store (2mins outside Montalcino) - Montalcino has some of the most amazing sunsets and for us sunset lovers, we wanted to take full advantage. In order to do just that we always made sure to book our dinners 15 minutes after the sunset and arrive 45 minutes early with a bottle of wine we purchased at Bruno Dalmazio so we could enjoy it overlooking the sunset no matter what village/town we were in. With that being said, Bruno Dalmazio has a vast variety of wine at all different price ranges. The staff was very helpful at helping us find a perfect wine for the occasion and within our budget. They also gave us some really nice wine glasses to enhance our experience and a drip stopper so it stays good to the last drop. The best!
Locanda Demetra - This little hill top restaurant that overlooks the vineyards of Montalcino is a local hotspot. They offer lunch and dinner for small groups of max 20 people so if you want to get in, I recommend booking it in advance. Since the restaurant isn’t really in town, you would only really find out about it if it was recommend to you by a local - but its great! The reason why it’s in my ‘play’ vs. ‘eat’ section is because they also offer traditional tuscan cooking classes! For €120 per person, we had a 5 hour class which included a walk around the garden, lessons on pasta making (which included both a with and without egg dough making demo and a lesson on how to make different styles of pasta), a traditional tomato sauce, a tiramisu dessert demo, and a bottle of wine with our meal. After we finished cooking we were then led outside and served the pasta and food we we made while overlooking the countryside and enjoying our bottle of wine. An afternoon well spent and definitely a fun activity to do while on vacation.
Podere La Ripi Winery - Little did we know but going wine tasting in Tuscany is not like going to wineries in Canada. Most tastings are done by appointment only and are often booked weeks, sometimes months in advance. Lucky for us, Podere La Ripi had an opening which we quickly snatched up with excitement. The tasting included a walk through the property and the wine cellar, interesting historic information about the region, and of course a tasting which comes in 3, 5 or 6 tastings. Tasting fees are waived if you spend over €100. The experience was lovely and I learned a lot about what makes a Brunello wine, the region and how it became popular for growing wine, different techniques in planting and growing quality grapes and why everyone is transitioning their properties into biodynamic vineyards.
Abbazia Di Sant'Antimo (Abbey) - This former Benedictine Monastery is really close to Podere La Ripi Winery so if you are going there for a tasting this is definitely a beautiful well maintained church and property to check out and take photos on the way. The abbey was original built as a place of refuge for pilgrims on their way to Rome and has since been very well maintained making it a beautiful piece of history to observe
Bon Di Santi Winery - The only reason why this winery is on my list is because it is absolutely stunning. Although this winery is famous for their wine and I would of loved to try them, the €450 price tag for a tasting was way out of my price range not to mention it has to be booked way in advance. It is really close to Montalcino however and you are able to walk around the grounds a little bit which is why I am recommending it. The Cyprus trees that line the entrance driveway make for a beautiful shot and the grounds are so beautifully manicured its worth going for just the photo opportunities.
If you are going to Montalcino, I hope you have a great time and enjoy your stay. If you come back with some of your own recommendations I’d love to hear them so feel free to pop those in the comments below!! If you have any feedback on any of my recommendations as well, I’m interested to hear about other people’s experiences and what they enjoyed/didn’t enjoy. Until next time - Arrivederci!