port jeff on the
long island side is a reasonable half way point.
if port jeff is not doable

port jeff is a long haul for sailing the usual winds of LIS. it is also a
long, long haul for sailing the usual winds of LIS and Block Island Sound.
There is no reasonable anchorage on Long Island between PJ and BI (Mt Sinai is
too close to PJ to be all that useful, and Matituck Inlet is reported to be
awfully shoal in spots these days).

It is 120 miles CI to BI. If you get lucky and get winds out of the North
(usually 15 knots or more) you can sail it in two days, either direction.
Three days can be easier, unless you wanna push the throttle forward quite a
bit. Also, watch the currents at The Race. They can be seriously against you.

If you stop at nortport you will have to stop in CT the next day.