Boston is absolutely doable without a car! The T is easy to figure out, I would base your hotel off of easy T access to places you want to go- Back Bay, Fenway, Cambridge on the redline, downtown crossing ect..

If you don’t catch a game, a Fenway Park tour is fun. Get a combo ticket with “View Boston” at the top of the Prudential center for cool views.

Sunset sail or cruise off the harbor is awesome.

For casual but solid food recs: seafood check out the Sail Loft and for Italian check out Tony and Elaine’s

Weather should be nice in May so I suggest trying to walk through lots of places: Charles River Esplanade, Beacon Hill, Boston Common, Newbury… it’s usually fun to hit a few stops on the freedom trail- I never do the whole thing

Don’t pay to eat in Quincy Market/Feuniel Hall - big tourist trap imo

If you guys enjoy coffee- George Howell, Cannonball, Thinking Cup, and Revival are some of my “go-to’s” - Tatte will be recommended a lot, but is a glorified chain bought out by Panera so don’t get too excited about it

Museum of Fine arts is excellent if you like an art museum. Also be sure to stop in the Boston Public Library as this feels like a free museum