Cortona does not have as big a nightlife as Rome, Florence, or Milan, but you can still go out and have a good time. There are several small pubs and clubs that you can go to for drinks and entertainment. Generally, what people will do is buy a bottle of wine and drink that before heading out on the town. After the bottle of wine, you can head out to the pubs and enjoy some drinks there. Some of the better known bars in the town are The Lion's Well , Caffe' Degli Artisti , and Route 66 . The nice thing about these smaller bars in towns like Cortona is that they serve the patrons and will stay open as long as there are customers. There will never be a true closing time, but it is expected that you won't be staying there until the morning. Every now and then some of these bars will have live entertainment. They are always a local hang out, however, so there will be plenty of people in there, especially on the weekend. Friday and Saturday are the biggest nights in the bars. If you want to get wine before you head out, it's a good idea. Because you're in Italy, wine is so prevalent and cheap you can literally get a whole bottle of wine for less than a glass of Coke.