Sounds like a Great Trip! I think your planned milage is reasonable and conservative, for your boat speed. You didn't say whether or not you planned on anchoring
out or staying at marinas
...or a mixed bag. That might help with options. And Yes, you'll probably motor
a fair bit!!
If you're doing this trip for the 1st time, I think there are some must see places and some ...would be nice..if you had time....and like you said you can always adjust as you go.
In between Salem and Plymouth you might check out Manchester Harbor...if you need to duck in somewhere. or as an alternative.
If the wind
were with you..I might jump over to Provincetown. Though it's too early in the season for the summer crowds, it is a nice place. ( even nicer without the crowds) You could make onset from there...or check out Wellfleet..my favorite cape cod
town...(a little tricky harbor , but then you're a Maine
Cuttyhunk ( mooring
ball ) could be after onset...and would set you up nicely for Block Island (great salt
pond) Where you could anchor
or pick up one of the town mooring
balls. I think Block Island is a must see!!! You could do Newport
from Cuttyhunk then over to block or visa versa....Block and Newport
are worthy stops..
From there..I think the Connecticut River is worth a look..either old saybrook or Essex...very pretty..easy entrance.....if anchoring
is your thing..check out north cove....if you want luxury ( saybrook point marina) ..quaint...essex..
in either case...IT's critical that you carefully time the currents at the Race
of long island! The Cape Cod
Canal, and the East River!!!
From Saybrook...I'd cross over to Port Jefferson NY...it's 40 miles..leave early..you're there in plenty of time...I really enjoy Port Jeff..and it's inexpensive ( moorings)
You can make city island from port jeff..easily enough, but keep in mind there is no diesel fuel
on city island...I'll pm you a great italian restaurant there...(.either fuel
up in port jeff..or duck into manhasset bay for fuel...
Time your East River passage
carefully....if you get it right, you may also carry a fair current
to the highlands....Wind against tide in the narrows can be a pain!....if you get a stiff south wind
against the ebb..you can duck behind Hoffman Island..and head
to Great Kills harbor on Staten Island..
The Jersey shore is pretty straightforward....the current
runs strong in Manasquan..watch the RR bridge..near the Brielle Yacht club...which is a good stop!
Your longest day!...will be the Delaware bay...so wait for good weather
..if you have to..Cape May is a great place to be anyway...
How far down the Chesapeake do you want to go?...Rock Hall has a great Reputation, then there's the Sassafras and Chester Rivers...
I hope to be taking the opposite route
by June!!...I'll be interested in your reports..if you get to post any news as you travel..
Best of luck!