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Gary,Shawn, no reason to venture 50 miles offshore - I would stay within 10 miles of the coast, easy trip, and if the weather gets nasty, easy ride into the inlets. Mystic Seaport is a neat place, and I've been there several times in powerboats and by land. When I was an freelance outdoor writer, one of the magazines I wrote for home ported out of Mystic and I had to go there frequently for conferences.
You'll love it,
Having made this same trip many dozen times, I am curious which inlets you speak of. I my opinion the only safe ones on the Jersey coast are Cape May, Atlantic City, Barnegat (graveyard of NJ) and Manesquan. All especially Barnegat are not easy ones. You should be prepared to travel at night if conditions are not good to transit the inlets.
Shawn, we have talked a lot about this and not to throw negatively on it i think this is to much to bite of as a first trip north. It's not about your experience but about the experience.
I will be heading north in mid August as we do every year. We have 19 days. IMHO and experience barely enough time to visit MV and not much else. MV is certainly doable, but you will be on a tight schedule pushing it even if you go straight through to Block from Cape May. I think this is to aggressive. Not the trip I would take as a first timer offshore and with two young children. Give yourself some time to gain some experience .
We gave done this expedition every year for 13 years and find its much more enjoyable to relax and spend time in one area sail between the interesting towns. The next year go back up and explore another area. This way your family will greater enjoy the area and see things which interest them instead of doing 60 to 130 miles of sailing only every day or every other day. Remember you also have to come back against prevailing S winds and put a couple of days in for weather. It would be different if you could get a few friends to help you get the boat up there quickly.
Logically one day to the Delaware. One to Cape May....36 hours or 2 days to Block. I day to the Vineyard.in best conditions. That's 5 days. Non stop sailing. 5 or six days back. That's 10-11 days just transiting. Not much time for seeing much else. To me not a very relaxing vacation.
Since it is your first time to do this I would dial back a little and enjoy this trip. That way maybe you will have a great experience. And your brood will want to do this every year. I would do Block -2 days Greenport-2 days Mystic- 2 days then back down the Sound to Northport or Port Jefferson . Down the East river to Atlantic Highlands. Spend 2 days on the return in Cape May.
In addition you don't have the battery power to be out this long without being at a dock a few tines. In addition is your radar working? The fogs a ***** when it comes in up there for a few days.
Either way you choose I be glad to help you with anchorages, restaurants and routes for your trip.