I've done this transit many times, and kept a couple of
boats in Fishers Island Sound (Noank).
You'll want to have a fair current with you. Check the venerable Elderidge book for the way to do it starting where you are, and plan to ride the current all the way to Norwalk if you time things right. it will make a good difference for your size boat.
check the currents at Watch Hill
Passage as the
water boils there when the tide is ripping and pulling the buoys down. Once through Watch Hill pass you can
head immediately to East Harbor of Fishers Island; wonderful, protected from all sides but the north
wind. no place to land though. if you want to go ashore
head to Stonington harbor, get a
mooring and then you can get over to the various bars and cafes.
Also, have a plan to go on the south side of Fishers Island, especially if you are moving with good speed, and then enter Fishers Island Sound via The
Race. Check the time of the flood current there to ride in, then you can tuck around the west end of Fishers and up into the West Harbor, also excellent cove in anything except north winds. no place to land there, if you want to go ashore grab a mooring from Spicers or Noank Shipyard. Seahorse Restaurant is fantastic and reasonable. also the tourist lobster places are at hand (though overpriced for what you get).
or you might enter the Sound at The
Race and continue to Westbrook, or New London, or the Connecticut River. lots of great places to spend the night.
the other thing to consider is the prevailing SW winds which are sometime W. this can be a chopping ride if you enter/ride with the flood tide. if you had a W or E wind at Judith you might head south towards Block then wait for the SW to start in the afternoon and come in on one long tack - I did that many times. you'll do
hull speed plus the fair current - fast and flat.
Once I waited for a low pressure cell to roll though CT/MA and it created an 20 kt ENE wind for me to blast from Judith all the way to Milford fast no stops. unfortunately it troubled the Sound waters enough to anger the Admiral, but worked like a charm for a fast sail in my 41' boat.
pick your wind, ride the flood, careful in Watch Hill or The Race. Enjoy.