If you want to drink a well-crafted cocktail in a space that allows for a really good conversation then go to the Spotted Owl. It is located in a historic space in Tremont and definitely has that speakeasy bar feel. What sets the Spotted Owl apart from other cocktail bars is their cocktail wheel (my favorite thing ever!). How it works: you get the board, you let the bartender know what you are feeling/your intentions for the mood for the night (e.g. to relax, reflect, regale or restore), then you tell them your taste profile. From there, you give all your trust to the bartender to make a unique cocktail specific to you. Very anxiety prone. I know. But have no fear, their cocktails ALWAYS come out amazing. It is my favorite place to go to for a drink before/after dinner or on a Friday night to unwind from the week.