Under The Tuscan Sun
Without a charity auction,
mixed with heavy pours of wine, and it just being way too much fun waving a paddle in the air with no personal consequences because it’s tied to your boyfriend’s credit card account, I would have never heard of the tiny little town of Cortona.
Probably because I have refused to watch Under the Tuscan Sun due to the movie poster screaming “THIS MOVIE DOES NOT PASS THE BECHDEL TEST AND PROBABLY HAD SOME UNCOMFORTABLE JOKES SCATTERED THROUGHOUT.” Just kidding. It’s just bad cover art and I do indeed judge movies by their covers. But, this early 2000s RomCom was based and filmed in the Tuscan town of Cortona.
Once Hollywood did its thing, the town shockingly stayed true to its roots. The town hosts tourists, but instead of embracing the quick cash grabs, it keeps its guests at arms reach. Not bending over backwards to make tourists comfortable has kept the town in its quaint state: the town still has a “rest time” every day where shops and restaurants shut down for hours, the town square is everyone’s meeting spot, and the cobblestone has not even been slightly touched to make the town more accessible for walking in heels (or driving a car).
Overall, if you want a quiet, super authentic experience with some of the best views your eyes will ever take in, I would 100% recommend stopping in Cortona. And if you do, here’s some recommendations for you:
FOOD:
La Dispensa
This was by far our favorite place to eat. There is the main chef who makes fresh bread and pasta in the window which automatically draws you in. But unlike most places with the “food in the window” gimmick, the food at La Dispensa is amazing. Have at least one person at the table order whatever the pasta of the day is–it will always be amazing. They also had homemade gluten free pasta and bread which was amazing for such a small town.
Make sure to go back for lunch and have the best sandwich of your life on fresh salty focaccia that’s pulled out of the oven right in front of your eyes.
Trattoria Dardano
On trip advisor, this is listed as a locals favorite. The waiters are sassy, the jugs of wine are big, and the food is very inexpensive. The overall taste of the food was nothing to write home about for us non-gluten free people, but my mom did say it was some of the best gluten free pasta she’s ever had.
Gran Caffe Signorelli
We grabbed coffee and drinks here every day while listening to live music in the piazza. They also have an espresso gelato machine that is worth trying on a hot summer's day.
Al Tocco
Our second favorite spot, this newer restaurant in Cortona with a young hot chef is definitely worth the stop. We did an early dining tasting menu and everything that hit our tongue was fabulous. I could see this modern concept being nodded at by some Michelin star critics in the near future.
Osteria Del Teatro
Speaking of Michelin Star restaurants, this once heavily decorated restaurant lost its star, and after dining, we can tell why. We were the most excited to try Osteria Del Teatro out of all the restaurants in Cortona, but came out of our dining experience disappointed by the food and service, and heavily creeped out by the women's bathroom.
Gelateria Snoopy
This is hands down the best pistachio gelato I’ve ever had in my life. We stopped by this place every single night for some live music and sweets.
Trattoria Pizzeria “Croce del Travaglio”
This was my mom's least favorite gluten free experience, but one of my favorite (heavily gluten) pizzas I consumed in Italy. The pizza comes out paper thin, but lacks no flavor. I recommend getting anything with the spicy pepperoni on it.
FOOD SKIPS:
Taverna Pano e Vino–it’s a tourist trap because of the great location, but the food and service was awful. There are much better places to spend your time, money, and empty stomach.
ACTIVITIES
Baracchi Winery
This place was divine. We did the tour with wine tasting and we wish we would have booked the full course meal instead. Not only is the winery gorgeous, but the restaurant on the property has a Michelin Star and is run by a female chef. If I went back to Cortona, I would stay at the hotel for at least one night and soak up the luxury.
Vespa Rental
This was so much fun and I highly recommend this activity to drive around Lake Trasimeno (or as I joked to Chris and my father’s dismay– Lake TrashMenO). The authenticity radiating through these smaller villages is palpable, and everywhere we stopped had breathtaking views. Just make sure you don’t accidentally end up on the highway like we did. :)
Museum
This museum held so much more than what meets the eye from the. outside. I would set aside 3 hours to walk through the whole thing. You’ll learn about how old the city of Cortona actually is (older than Rome), see artifacts that date back further than I can wrap my head around, be in the same room as Egyptian mummies (we know how Europe loves to take Egyptian artifacts for their own), and even get to deep dive into more “modern art” (still older than America though).
Walking Tour
We did the walking tour on our last day and thought, “what will we learn about this small town that we haven’t already discovered over the past 6 days…” and boy were we wrong. We learned so much in this hour-long tour and I highly recommend doing it on your first or second day in the town.
See The Under the Tuscan Sun House
Pretty self explanatory. But you will have to look up the address then go on a pretty long hike to find it! So wear comfortable shoes!
TIPS:
The train stop closest to the heart of Cortona is Camucia-Cortona. Pre book a bus to the Cortona Centro - Piazza Garibaldi when you book your train tickets (if you’re not getting a car), otherwise it will be impossible to get up the hill.
There are no ride services around so you either can pre-book private transfers to and from your activities (which is around $150 per activity) or rent a car while you’re there. The car rental place we used was a couple blocks from the train station. So, if you are planning to do any wine tours, vespas, cheese making etc., rent a car right when you get off the train. Our car was $100 per day. Also, take the SMALLEST CAR THEY HAVE not the newest or nicest. SMALLEST. The streets are the most narrow and steep streets you’ll ever see in your life. I had to hold my breath and pray to Jesus every time we drove in and out of the town. (They didn’t ask for an international drivers license… but I can’t say I would recommend not having one… cause that might be illegal… ya know?)
The town is built straight up a hill. So be prepared to only wear tennis shoes.
