Remember the movie Under the Tuscan Sun? The classic story of woman divorces man, moves to another country on a whim and ultimately finds herself (and of course another mans). Well, it was filmed in this teeny tiny Tuscan hilltop town and, based on the plaques that you see dotting the cobblestoned streets, it is their proudest claim to fame. We rewatched the movie recently (okay I rewatched it…I made Tim watch it for the first time) and it honestly does not do Cortona justice. Even if it is a cinematic masterpiece ;)
We stayed in Cortona in early September and it was the perfect place to base ourselves for a lovely 4 days spent in Tuscany. It’s a picturesque 1.5 hour drive from the Florence airport (or a 2.5 hour train ride) and close to the major wine regions of Montepulciano and Montalcino, plus the larger towns of Arezzo and Siena. Outside of its ideal location, Cortona’s perch on a hilltop gives you incredible views down into the Tuscan wine valley below. The town itself is cute enough to explore for a few days without ever leaving and boasts some of the best cuisine that we have tried in our nearly month long trip throughout Italy (which trust me…is saying a lot!).
If you do find yourself in Cortona, I highly recommend this Airbnb that we stayed at. It was massive and the decor gave me such luxe Tuscan villa vibes, which I’m always striving for. Plus it came with parking! You’ll just have to be comfortable driving in alleyways so narrow that you have to turn your mirrors in and make 3 point turns in a crowded pedestrian streets (thank God Tim was driving).
But whether you’re staying or just passing through, here are some things that we’d recommend!
MANGIA (EAT!)
Tuscany is famous for a specific type of cow called Chianina. It is one of the oldest breeds of cattle having been raised in this region for the last 2200 years. And it is DELICIOUS. No matter where you eat, you have to try a Chianina steak in the traditional style called “Bistecca alla Fiorentina”. And make sure to get it cooked to their suggestion which is typically medium rare. My Dad would claim it’s “still moo-ing” because it’s so pink but, trust me, it’s incredible. Truly all the food we had here was.
Osteria del Teatro (Cortona)
A classic bistro on an adorable side street off of the main square. The food was amazing and the ambiance was great. We got the stuffed squash blossoms, goat cheese ravioli in walnut pesto and bistecca Fiorentina in a foie gras sauce with shaved truffles (really loved the “more is more” approach here). Plus finished it off with a shot of limoncello. Chefs kiss! Call 1-2 days beforehand to grab a reservation.
La Bucaccia (Cortona)
A very popular restaurant set in an intimate wine cellar setting. They do two seatings a night (I believe 7 and 9:15) and it’s popular for good reason. We had a pasta with fresh mushrooms and truffles and duck in a cherry compote and they were both great. The table next to us had the bistecca and it looked amazing, but we needed a break from steak so we switched it up. We actually called the day before and got a reservation but you might want to try a few days in advance to be safe.
Osteria Il Carroccio (Siena)
Delicious pastas, appetizers and meat dishes. This restaurant is right off the main square and fills up for both lunch and dinner. We stopped by for lunch and had to wait in a line for about 10 minutes before being seated. We started with an artichoke tart with freshly shaved truffles (I’m picking up on a theme for myself here…) and then had Carbonara pasta and penne pasta in a spicy red sauce with shaved goat cheese. Incredible.
If you’re wondering if we’ve gained 10 pounds on this trip, the answer is yes. And I don’t regret one bite! Our Airbnb Host, a Cortona local, also recommended these places that we didn’t have time to check out: Ad Braceria, Ristorante La Loggetta, Trattoria Dardano, Beerbone Art Burger, La Taverna del Gozzoviglio.
BERE VINO! (Drink Wine)
Of course this is one of the main reasons you’ll come to Tuscany. We had a car so we were able to drive from place to place which was really nice. We tried wine in the regions of Cortona, Montepulciano and Montalcino.
Baracchi Winery (Cortona)
This estate was STUNNING! The winery is part of a five-star Relais Chateau hotel and includes a Michelin rated restaurant. We felt a little out of place rolling up in our Jeep next to all the Porches and Maseratis, but such is life. You can choose from a traditional tasting or to include food pairings and they all include a tour of the vineyards and cellar. We did the tasting and it was a great value for $25. We especially loved their sparkling rose and white varieties.
La Combarbia (Montepulciano)
This was by far our favorite stop in Montepulciano. It’s a small family run winery that has been producing wine in the region since the 1960’s but only started selling bottled wine and ramping up production in 2016. They are known for their Vino Nobile di Montepulciano DOCG which is made from the best Montepulciano grapes. The DOCG is essentially a certification that the wine came from that particular region and is produced in the correct way (a good representation of the product). We don’t love very tannic wines so we especially liked their Super Toscana which has Merlot grapes blended in. The tasting included a visit to their vineyards and tasting of 8+ wines and the guy who gave the tour, the only other employee outside of the main guy, had lived an awesome life so he was great to chat with.
I Cipressi (Montepulciano)
Another family run and very small winery in the region. This was an adventure because the son who normally gives the tastings (and importantly speaks English) was on vacation so we were with the father/winemaker/grower who spoke zero English. Google Translate became our best friend. The wines were delicious and he made us a beautiful and fresh cheese and meat board. It was fun to meet the older generation who has an incredible passion for wine making.
Mate Winery (Montalcino)
This area is known for Brunello which we really enjoy. This property was beautiful and the wine was delicious, but a little pricey. The winery was actually opened by an American couple who moved to Tuscany. Definitely worth the visit!
Visit the Neighboring Towns
Arezzo
A short drive from Cortona, Arezzo is the main town in this region with a large “Old Town” and a lot of newer shops and restaurants. There’s great parking all around with access to the town via escalators. We felt like we were entering Duloc, the medieval town from Shrek, as we were welcomed over speakers to this magical city. It’s a great place to wander around. We enjoyed visiting the main Church and seeing the square. It was actually decorated with house shields as they had just finished a festival called The Joust which they do the first Sunday of September every year.
Siena
This town really was magical. Siena has the largest University in Tuscany so it has a nice young energy. We parked outside the main city and walked in. We enjoyed lunch at Osteria Il Carroccio and just wandered around. I really loved that all the street lamps around the city are works of art.
And of course, just get lost in the streets of Cortona. Stop for a Campari Spritz and aperitivo in the main square and enjoy the live music. Force the local cats to allow you to pet them (my personal favorite pastime). And find a perch on the hill to watch the sun set over the green valley of vines below, sipping a bottle of wine that you bought from the winemakers that day. I venture to guess that you won’t find a more perfect Tuscan town than Cortona. I know we will be back!
Wandering around Cortona
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