Get a drink at the top of the Omni hotel (John Davenport’s). The view is nicer during the day.

Pop into the Yale Art museum and chill out for a bit in the courtyard at ground level. One of my favorite spots to relax because you feel like you’re in a quiet little fortress.

While we are sticking with Yale things, pop into the Rare Book & Manuscript library.

Go to Trinity in the morning to watch a soccer game and drink. I am not a Liverpool fan but they have the strongest following in the city and it makes for a neat spectacle as a neutral.

Edit: adding a weird one, get a panini and a coffee from owl shop in the afternoon. The place is usually dead at this time, so you don’t have to deal with smoke if that’s not your thing, and they seriously make a great sandwich/coffee. It’s a really unique space and worth considering for your staycation checklist.