The East River used to be full of sailboats with no engine
Going west along the South Side of
Long Island without an engine is no fun. The prevailing
wind is against you. The swell is nasty. There are no all
weather deep inlets. You can't
anchor.
Long Island Sound has none of these negatives and a tide that's more reliable than any engine.
Get a copy of Eldridge
Plan your whole trip based on tide. This will mean
anchoring at weird times to wait out an adverse tide. And
anchor for the night in big open bights like
Fisher Island - don't try to go up some channel. Because the days are so long, this will be much easier than if you were doing the trip in October.
I wouldn't try it without an engine in reserve. It sounds like your engine does
work well enough to be started and get you out of a jamb. And don't try the East River with no
wind. You might have to wait a day in City Island - not a bad place to wait. If you time the
current, the East River is only an hour transit. You might just leave your engine on in neutral the whole way.
Be a
member of TowBoat US or SeaTow. Call them before you are in bad trouble.