We are surprising my dad for his 50th with a trip to Boston to catch a Red Sox game towards the end of May. Right now the plan is to fly up Thur morning and leave Sun and catch a Fri/Sat game. The only thing I know for sure that we will do is the Fenway Tour and the game.

I come to the experts for hotel recommendations, bars, restaurants, tours, or any other can't miss for Boston. My parents aren't big travelers so I definitely don't want to disappoint them.

You have to follow the Freedom Trail. More history than you'll know what to do with. The tour of the Paul Revere house is worthwhile (the only 17th century home left in Boston) and the walk there takes you into north Boston and some fantastic Italian food. Follow the trail to the USS Constitution. Oldest vessel still on active duty in the Navy and a fun tour.

There are some other good sites: the Sam Adams tour is fun, though it's in a bad part of the city. The JFK Presidential Library is pretty cool. If you have a car, Concord is a really great day trip as is Salem.

As far as restaurants, you'll want some seafood. The Barking Crab and James Hook are casual sit-down restaurants with good lobster rolls.

Pretty much what he said. Freedom Trail is great, I would recommend the walking tour vice the trolley if your folks can get around well.

If you go to Salem, don't visit the witch museum. Total rip off.

Thanks for the advice. We booked our flights last night so I'm getting pretty excited. Right now all we have planned is a Red Sox game one day and the freedom trail another day. That leaves one open day.

For lodging, I was looking at VRBO around Back Bay instead of hotels. Should we stay in that area or somewhere else?

Stay in back bay. Lots of public transit options. Actual easily walkable to Fenway from that neighborhood. Or very short cab rides to most places.

Enjoy your trip. All this snow will hopefully be gone by then!