It's not that far from Rockport to Cape Cod(150 to 170nm depending on track), but it's about the limit of what is feasible for a 2 week vacation for us.

I was watching the sunset from Monhegan after motoring into a headwind since 5 am from Isle of Shoals. I broke the return up into 3 pieces; Onset to P-town, P-town to Isle of Shoals, IofS to Monhegan. The last two are pretty long day trips, I've done them before.

On the way down, I went overnight from Rockport to Onset in about 32 hours, almost all under power in little wind, building to great wind on the nose. I've done that before, a few times. A little boring at times and the last 8 or so hours are always the hardest. But after a very long nights sleep, it's over, and you're there.

My preference is to sail of course. I've done it downwind and up wind in a continuous sail. Either time, or direction, that's been the fastest. Those trips have been the most fun too.

If you break this trip into easy day trips, it can get quite long, but it's great if time allows. I've done that before. CC, Ptown, Marblehead, Portland, Boothbay, Monhegan, Rockport. Pretty soon, you're taking a week, conditions can make it quite a bit longer still. Alot of weather is hard to predict after 2 or 3 days.

I find that a lot of time is burned up leaving the "track" to veer off into harbors and lay over anchorages. There really is not a single option even close to the rhumb line to overnight. That line is a time saver.

The first thing that would improve the trip, is allow enough time to wait for favorable winds.
Often, they're just a day or two behind. How often do you do that? We had two weeks so waiting wasn't much of an option.

I enjoy the 2 week trip, it's long enough to really feel relaxing, yet can fit work or other time constraints. When we did some cruising years ago, seems we spent long blocks of time "waiting for weather". That's fun if you want to be there, but doesn't work on the dreaded, schedule.

The next thing we all deal with is crew. I've done this trip a few times overnight with my family. That's a whole new layer of what you can accomplish, or can be a restriction and add time. I've had it work both ways. We have no problems there, we just work out what works best for everyone each time. Crew is a wild card for most of us, family or friends.

I know many here have made this trip, and there are no doubt similar ones up and down this coast and the west coast. We usually sail close to home on this vacation but get the itch to stretch our legs a bit sometimes.

Anybody have any tricks or tips they use to make passages like this? I'm interested.