I would also go up Long Island sound
. You could have great weather
in October but it could just as easily be cold and rough. Big difference between early and late October!
As mentioned, tidal current
is important in these waters. get a copy of Eldridge and build a plan around the tide.
Days will be getting short and it may be surprising cold. Be sure your crew packs warm gloves, socks and hats. You could lose some days to bad weather
so you may want to bend your "night sailing" rule
. Some predawn departures on good weather/tide days could make a big difference. It's also very easy to transit the Cape Cod
in the dark. If you have a chartplotter
, one good plan would be to overnight through the canal. Dawn will come well before you get close to the hazards of Boston. Of course, be sure everyone wears a harness on deck
Many, many safe anchorages
and the crowds will be gone. Montauk, Newport
, Block Island, and Cuttyhunk are all special and easy to enter.