In December 2015, I spent 8 nights in Cortona. Here are a few of the restaurants I enjoyed:
Trattoria Dardano: I loved this restaurant so much, I ate there 2 nights. This family run restaurant is so charming. My favorite dish was the pici with duck sauce accompanied by grilled vegetables. The house wine is delicious and they offer local wines as well. The second visit I tried the tagliateli with ragu and the pollo, this time accompanied by a Montepulciano Rossa. Both meals were delicious with the kind of excellent service you become accustomed to in Cortona.
Cortona Bistro: I couldn't resist this place on a warm December afternoon because the umbrellas were up and they were serving at the outside tables. Such a sweet place to eat lunch on a sunny afternoon overlooking the Chiesa Di San Domenico. The waiter was patient with my limited Italian - even though he spoke fluent English - as I ordered a delicious caprese salad, ravioli with speck, pumpkin, and riccota accompanied by a delicious Savignon Blanc.
Trattoria La Grotta: A restaurant just off Piazza Della Repubblica was very low key and relaxing. Here the locals were welcomed warmly and I was tolerated :). Tried bruschetta con lardo - good but will likely need to try again somewhere else to get a real feel for it. The stinco dei maile was delicious and was perfect with another local red.
Ristorante Il Cacciatore: I never would have tried this restaurant had it not been for a suggestion from the Travel Forum. The visitor is directed to this restaurant down a quiet street by a neon sign - usually a bad sign for a tourist! However, after the suggestion I decided to give it a try. Great decision! First, the food was spectacular. A delicious caprese with the most wonderful buffalo mozzerella followed by a heavenly Mafita pasta with prochutto and pumpkin! A local red followed by a delicious limoncello made for memorable dinner. The food was only surpassed by the friendliness of the wait staff. The woman was friendly and even helped me decide to visit Eremo Le Celle (monastary above town) based on a stunning photograph hanging on the wall. She went as far to get out a town map and help me figure out the walk.
Fufluns: Just a few steps down from my hotel, this was the best pizza I had! On the recommendation of the gentleman at my hotel, I had the "young flour". It makes all the difference - very light and not fililng at all. A simple tomato and prochutto pizza was followed by a wonderful insalta mista and accompanied by yet another local red!
Bottega Baracchi: I waited days for this place to open (in December only open Thur-Sun, I think), but it was well worth the wait! This new restaurant is owned by the family that runs Baracchi Wines and other eateries in Cortona, including a spa. I was so glad I splurged on this dinner! The waiter helped me choose a Barrachi Ardito - so great and worked perfectly with the wonderful ribollita which was warm followed by a beef stew that was heavenly! Finished with biscotti and vin santo - beyond description!