Our much anticipated pilgramage 9 (we travel to NE most summers) begins in 10 days on July 10. Our anticipated stops include Cape May, Barnegat Lighthouse, Atlantic Highlands, through Hell Gate to Northport Harbor , Port Jefferson, Westbrooke Harbor, Mystic Seaport (July 17 and 18), Block Island (July 19 and 20), Guilford, Huntington Harbor, Atlantic Highlands, Barnegat Lighthouse, Cape May (July 24 and July 25th) and then back home to our club on the Chesapeake in Rock Creek.
We would also love to meet up with any of our extended sailnet family if we are going to be in your area when you are out. Would be nice to put a friendly face ( or scarey one) to the comments I read here.
There have been a fair number of posts about places to go, things to do, and where to stay, including some by me. I'll give a few thoughts, but I encourage you to search a bit.
Give some thought to stopping in Port Washington (Manhasset Bay) on your way to Northport. It's the first good harbor on Long Island after you enter the Sound. Very good holding, can grab a mooring if you prefer, and very nice and accommodating Yacht Clubs. There's also a water taxi. The town has some nice stuff too. A park for the young ones, if you have them with you. A number of good restaurants (Louie's is a landmark, and is a dock-n-dine). There's also a West Marine and supermarket walking distance from the harbor.
Port Jeff gives you lots of options in terms of mooring, dockage or anchoring. You probably already know that considering that you're going there and you indicated that you've been there before.
A place you have not mentioned in Milford. It's right across the Sound from Port Jeff, and it's a nice harbor. You need to go dockside or tie up to one of their floats. There are a number of clubs and marinas, and you're walking distance to town.
In Westbrook, are you planning to stay dockside or anchor behind Duck Island? I've done both several times. Pluses and minuses to everything. Dinghy distance is Bill's Seafood, which essentially is a greasy spoon, but a fun one.
An entire area you left off, which you might want to consider and thus skip a place like Guilford or maybe even Huntington (considering that you're going to Northport on your way out), is the Shelter Island/Gardiner's Bay area. This area offers a number of harbors with tons of stuff to do, and some of the best sailing I've done has been in Gardiner's Bay. You have Greenport, and if you go there stay at the Mitchell Park Marina (it's a new municipal marina right in the heart of town with beautiful floating docks). There are bars, restaurants, shopping, and even a carousel right there at the marina. If you go, as for Jeff the manager. It's a great spot and the town really is in a period of revitalization. In this area you also have Sag Harbor, which is a town, not a harbor, though it has a beautiful harbor filled with mega yachts. On Shelter Island itself you have Dering Harbor (not my favorite), Coecles and West neck Harbor. The latter two give you seclusion and great scenery.
You also didn't mention the Connecticut River, which has Old Saybrook and Essex, which both boast nice downtown areas with restaurants, shops, and, of course, bars.
Just some of my 2 minute thoughts. I know you can't get everywhere in a single trip, but it sure is fun to try!
We'll be out east from July 11-25 or so. We'll likely be farther east (Block Island, Martha's Vineyard and Nantucket the first week) than you will be, but you never know.