My (not a frequenter, but having cruised a bit through up there) is that there are several very neat harbours on the North Shore of LI -- but they are a bit far apart after you get past Huntington until you get closer to the Sag Harbor end of LI.

You really would be criss crossing between the Connecticut side. There are some interesting places, but I think the time of year, whether you're anchoring (sometimes limited), picking up moorings, trying for slips, need AC for comfort, etc. It can certainly get crowded on the 4th of July and in late July and August.

The late July and August period is pretty hot (especially, it seems to me) on the CT side. The current and light winds become a factor.

Tell the experts (not me) some more, and they could probably guide you a little better.