Posted By:
AlMy 2 cents...
Stay at the airport Hilton and take a taxi to Fenway. It won't be cheap because of potential traffic delays. Reversing course is a snap, take the T back to Logan (airport stop). You get on at Kenmore square (blue line I believe) then change over to the green line to the airport. Google Boston MBTA maps for a color grid of the system. This allows you to drop the luggage, freshen up a bit and be on your way.
Take the T back to the Hilton (airport stop). When leaving the game, you will cross over the Massachusetts turnpike, (parallel to the 3rd base line) and when it joins Kenmore square turn right and down just a bit on the right is the entry to the T. You can almost follow the crowd or simply ask, people are pretty friendly...UNLESS it's a Yankees game and you have Yankee's gear on...NOT recommended!!!
Hope it works for you, enjoy the game.