I would want to take a 3-4 day break in the trip to do some work and then resume the sailing. My 4GLTE in New York is faster than my cable modem, but it is the security that they demand. In terms of speed I just need something more than dial up or DSL. I don't need much bandwidth. Just downloading medical records of about 100-150 pages in PDF and then uploading quick 2-4 page word files.
Since I work Mon-Wed, I can leave RI on a Thursday, sail for a week and a half, then camp out and work for three days and then finish the trip. This way I get three and a half weeks of vacation but only have to take off two weeks.
I could rent a car and go back and forth, but I think it would be more fun to stay up there.