Chios Town offers a few distinct areas for nightlife, suiting different preferences.
The central waterfront area, particularly along Leoforos Aigaiou, is where you'll find a concentration of cafes and bars that transition into evening spots. Many of these establishments offer outdoor seating with views of the harbor, and they often play popular music. It's a generally relaxed setting, good for a drink after dinner.
Moving slightly inland, around the main square (Plateia Vounakiou) and the surrounding streets, there are more traditional tavernas and a few bars that cater to a local crowd. These spots might feature Greek music and have a more casual, neighborhood feel.
As another option, some of the smaller streets leading off the main waterfront area, especially around the Castle, have a few boutique bars.