Check out the Yale are museum! It’s free on chapel street. Group W bench on the same street is a historic little head shop that has great souvenirs and jewelry. Check out Wooster square if you want some pizza and Libby’s for Italian pastries. Ordinary and Owl Shop are my favorite bars and they both have a great vibe. Walking up east rock to check out the monument and the city below is always nice if you’ve never done it. And finally lol, union league cafe is an amazing special occasion restaurant. I also like shell and bones for great seafood and oysters and a pretty waterside view. Tavern on state is also worth a try for a nice dinner but I’ve honestly had mixed experiences there, and if I’m planning to spend that much money on dinner I want consistency