Long Island Sound
has a mix of destinations, and where you go is going to be largely a matter of your goals and tastes. Some of the more populous/busy places have been mentioned, like Mystic, Newport
, Sag, and even Block. If you want to "get away from it all" there are a number of other places like Essex, the Elizabeth Islands, and parts
of Peconic Bay. For example, instead of going to Sag you might want to go to Smith Cove or Coecles Harbor on the SE end of Shelter Island, the whole end of which is a nature preserve. Smith has a gorgeous curving unpopulated beach, but is still a 10 minute dinghy ride to downtown Sag. One benefit to lingering in Peconic Bay is the water
which is unusually clear and clean for a semi-enclosed coastal bay.
If you tell us a bit more about what kind of experience you're looking for, you'll get some great, and more specific information here.
Tides and currents in the Sound are variable. In some spots the tide is @ 5-6', so worthy of close attention. Currents can be considerable in specific places, particularly in the eastern sound. For example, the current
getting into and out of Woods Hole can hit almost 4.5 knots. I would suggest you make sure that the boat you charter has a 2014 copy of Eldridge's Pilot and Tide book on it which will give you an excellent overview of tide/current info, easier to survey
and digest than what you'll get from your chart plotter: