Re: Marblehead to Hampton, NH
Nice trip either way. If the sailing is good with winds from West or South, I'd go to Rockport and spend the night in Sandy Cove if you have a dinghy, or in the harbor if not. Call the harbormaster and they will take good care of you. It is a wonderful stopover.
If its snotty off Cape Ann (winds out of the North or NE) then I'd opt for the Annisquam. Going through the Annisquam is pretty straightforward. Pass each buoy on the correct side and you will have no problem. There are some sharp bends, some close to shore, but is not difficult. In Gloucester, you will have to wait for a favorable current passing into the river via the Blynman Canal. I'd stay away from max current on my first time through. You can go through against a mild outgoing current. There will be minimal traffic if you are going through in 3 weeks, but even when it's crowded everybody just seems to find their spot in line. Call the Bridge tenders and they will talk you though. When you come out the other side of the canal, everything calms down. There is a railroad bridge around the first bend that is usually open but will open on request. Then it's just a couple of miles of easy going in a beautiful salt marsh. Follow the channel out the river as it turns east for a while, then you are in deep water again. You can head straight for Hampton Harbor from there.