Hi Matt,
You already know how much fun the Boston Islands are, no doubt. If you’re into geocaching there are some caches out on the islands.
From Gloucester it’s fun to go up the Blynman Canal and Annisquam River. You can beach it and swim/walk in the water on the east side of the river in Annisquam, and see the cottages on floats. There is a restaurant with a dock in Annisquam on the west side.
You probably know about Rockport. Tough to get a place to anchor – try Pigeon Cove, and hike to town. Unfortunately, it’s a dry town!
Oh yeah, do you know how Halibut Point got it's name? It has nothing to do with the fish Halibut.
From Annisquam, go up the Essex River to Essex. You can tie up at the restaurant there, and there are antique shops. All the way up, is the Essex Maritime Museum, which sometimes has space to tie up. The nearby town dock only allows tie up for a few minutes. The outer harbor has lots of shallow rivers to explore, and you can beach at Crane’s Beach back side to wade and swim. Don’t try this in July due to Greenheads.
From there, go into Ipswich Harbor, and up the Ipswich River to the town dock, then walk into Ipswich.
From Ipswich Harbor, take the Plum Island River, only at high tide (I have a shiny prop from ½ tide) to Newburyport. You also can go up the Parker River from Ipswich/Plum Island sound. All this area is a National Wildlife area that is famous world wide for the birds.
Newburyport has tie up at the town docks. They charge by the hour when busy. Newburyport is fun to explore with it’s restaurants, museum, shops, and antiques. I recommend Angies Restaurant which is like a local diner with tasty Greek foods, but there are many up scale restaurants there. The book shop and Museum sometimes have local interest publications.
For an interesting trip, go up the Merrimack all the way to Haverhill. It is slow due to No Wake zones, but you should see Eagles.
When you want to go north of Newburyport let me know. I keep my boat in Newington NH, just off the Piscataqua, and have done all the coast to Penobscot.
Rick from Maine