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 and
weather 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 sailor! )
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!