Welcome, good to have you aboard.
Thinking some thin water
and moving moving bars
in Moriches bay/inlet. If your draft
allows and enough
to navigate to Shinnecock inlet might be option.
Believe been a lot of movement since Sandy so suggest you
talk to Sea tow/us boats skippers or coast guard or both.
Under impression many experienced sailors will not do Moriches inlet.
You want a good patch of favorable wind/weather once outside as is
approx. 45 mile (10-12 hrs.) to Montauk with no place to go after Shinnecock.
Is good as days will be long in June.
Have done Orient to west most LI sound in one long overnight and have done same
taking a week. (Could spend a months in LI sound if you had the time.
Once around Montauk Pt. you must time your passage thru the race
or plum gut with
and have enough time with favorable current
to push pass eastern Long Island
where you don't want to deal with opposing stong current.
On Long Island side, from Orient pt to Mt Sinai/Port Jefferson, approx 40 miles, is only one inlet Mattituck and approx mile up Mattituck creek is lovely basin/anchorage, very protected.
Port. Jefferson and west on LI side have good bays with easy access to anchor
on Ct side many good ports/islands, not always easy/straight forward access but
very worth while.
Can pick up a guest mooring
at Steppingstone marina, my marina just west of Manhasset bay on LI side and say hello.