And have talked about it with you.

Having done an overnighter to-and-from Salem to Boothbay, we're less inclined than I once was to choose that approach. The way north, all under sail, steering by the stars, was great. The return trip, all under power and fewer stars to see in the southern hemisphere (and no autopilot), was much less fun.

We used to make day hops from Onset and found ourselves stopping short of Cape Ann. We now stage from Duxbury and can make it to Isles of Shoals. But it's a looong day and arrival after sunset is the norm. Below is a slightly earlier arrival; we'd stopped in Cohasset after a late start from Onset. We've also tried P-town but, as you say, entering and leaving harbors usually costs a lot of time. P-town is a good (or bad if you wish) example; so it Plymouth. We once stopped in Portsmouth when a strong NW would have made IofS uncomfortable, but it, again, is a long way in and out. (The next trip we stopped in IofS anyway with a 30kt NW and had fun picking up moorings!)

There are two stops which are on (or close to) the rhumb line: Isles of Shoals and Jewell or Cliff Island in Casco Bay. If not too tired from the previous long days, you can then make it to Penobscot Bay in another day from there.

Back in Mass Bay, two places to anchor in proper conditions are outside of Cohasset on the South Shore and behind Great Misery Island on the North Shore. Neither involves too great a deviation from your course.

It's all a matter of the time you have (as others have said) and the weather. We've been lucky in six two-week trips to have had little bad weather, either rain or fog, and seen many of the wonderful islands in Pen Bay. And always made it to work the following Monday!