I used to visit a friend in RI regularly about ten years ago and at that time RI was just about as bad as MA. I don't think the laws have changed since then, but I haven't made any effort to follow it closely since my friend moved south.
I would second the suggestion to either fly out of Portland or Bangor with the guns checked through to the final destination, or just ship the gun(s) to yourself at your friends' address. It is completely legal to ship guns to yourself (UPS or FedEx, you can't mail handguns unless you're an FFL, and although you can legally mail long guns many post offices don't know it). The only caveat is that your friends cannot (legally) open the guns -- only you can open the package(s).
Flying, eh? Your tough -- I won't deal with the TSA unless I'm flying internationally. I've told my wife if we go anywhere in the U.S. I'll drive. If she wants to fly, I'll drop her at the airport and meet her at the other end.