How long would it take a casual but experienced sailor to sail from eastern Connecticut to southern Maine?

I'm working on a writing project and the need to know about how long it would take a relatively small boat, with a very small crew to sail from eastern Connecticut to southern Maine in the summer months. Moreover, when people travel like this is what usually dock at night and find places to stay shore, or pier and sleep in their boats? Even relatively small sailboats have the ability some people sleep in them? And if there is only one person capable to sail the boat, and one other person on board, how many hours per day could reasonably candle before burnout? Finally, how many mph does a sailboat trip? FOLLOW-UP: Any discrepancy between "three days" and "a couple of weeks" – anyone care to tip the balance in a way or another? Thank you!

That's a lot of questions by just two points, but here goes. It's 366 miles of New Haven nautical Portland, ME. A an average speed of 5 knots, it would take 3 days to transit this distance, non-stop. If the ship was fully manned could go non-stop, or at least a stop. Short handed sailing with a single sailor, 12-14 hours per day would be a typical routine. If there is a cabin, sailing sleepers have bunks. "Open" ship would not. To save costs, everyone went to sleep on board. Otherwise, you need a car or taxi to and from hotels. They can eat the evening meal ashore and cook other meals on board.

Bikini Sailing Crew 3