Vernon Jordan was a prominent summer resident of Martha's Vineyard.
The Clintons used to visit him during the summer every year even during Bill's presidency.
Then Obama became a big Vineyard person too and bought a big place there about a year ago.
I went to high school in Boston and my girlfriend had a place on the Vineyard so I went a lot. If you have ever been there, it feels touristy in Edgartown or Oak Bluffs, but when you get out to Chilmark and other towns, you might be the only one for miles.
Also, the airport was tiny and always felt very casual. Lots of teenagers with important jobs for the summer. Some of my buddies were cops for the summer. I shit you not. You think some high school kid is going to insist on searching the presidents private jet etc?
Might have been a good place to smuggle into.