Sounds like some of the guys from my fleet in MD may want to do the race & am thinking you could convince them to ride with you back to the DC area on your way up to Boston. Let me know if you want me to ask around.
Here is the info on Miami to Key Largo. Its a dragrace to the Keys with big boats, cats and even wind surfers ...a great party the night of the race.
Apr 19 -- Miami-Key Largo Race, 1st of the Triple Crown of Distance Races, Miami Yacht Club, Miami, FL
You should try to do Hogsbreath too since the flights from up north are crazy cheap, I heard this year it is going to a one day format which could be cool from Islamorado to KeyWest.
Apr 26-27 -- Hogsbreath-Keys 100, from Key Largo to Key West, 2nd of the Triple Crown of Distance Races