I'm from Huntington, and we've gone up to
Maine several times, so I know the
route well. We almost never stay at
marinas, so can only talk about
anchorages.
We usually go overnight from Huntington to Fischer's Island Sound, choosing the time as best we can to arrive at the
end of the ebb tide. That way, you have the ebb with you when it really matters. There are several little protected coves to anchor in, but if you anchor in West Harbor you can go ashore for a walk.
If I want to break up the
passage, you don't have too many great options, which is why we bite the bullet and just get it over with. I personally love sailing at night. However, the Thimble Islands are a good place to stop and anchor, if the
weather is relatively settled. Very pretty, easy in and out, but you can't go ashore.
The New London city marina has VERY inexpensive moorings, and they are nearly always available. They are right in front of a pier with a restaurant and there is often
music in the evening. Very few cruisers put in there, because the city has a kind of gritty reputation, but they are working hard to come back and we had no problems and a lot of fun there. You can anchor right outside the
mooring field, too, but the moorings are so
cheap, we didn't bother.
Mystic is a great stop. Right across from Fisher's Island. We don't bother taking our big boat in to Mystic, but anchor off Mason Island and take the dingy in.
I'm not crazy about Block, but worth stopping once if you've never been. It's stupid crowded and I've never been able to get a mooring. The anchorage is very deep, and very crowded, so its hard to find a spot big enough to put out sufficient
scope. Honestly, unless you like drunken crowds and dragging powerboats, I wouldn't bother.
Newport is also a fun and easy stop. We have always been able to anchor near the Ida Lewis Yacht Club. You get there and think, "We'll never find a spot!" but there always seems to be room. If not, there are plenty of other places to anchor nearby.
Cuttyhunk is great. We always anchor outside and have never gone ashore. It's just an overnight stop for us, but one of these days we are going to dingy in and take a look!
We almost always anchor in Onset harbor, to wait for the right tide to go through the
canal. Again, we've never not been able to anchor there. There always seems to be room. Just be careful when entering the Onset channel. There is a vicious tide
race right at the channel mouth. If you can hit it at the very short slack tide, do so. Otherwise, be prepared for a few moments of frantic
steering. It's only the first few seconds, then you are in calm
water.
We always sail direct from the
canal to Penobscot Bay in
Maine, so can't help you with the rest of your itinerary, but crossing
Cape Cod Bay is dead easy. For us, it's just the first part of the long
passage up to Maine. Kind of a break after the canal or the open Atlantic. Lots of whales there in the right season, so keep your eyes open!
Have fun!
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