I will opt for the GPS, and hopefully make the trip in 2 days. If the weather looks bleak for the day 2 trip from Westbrook through the Gut I will continue to dock in Westbrook until favorable day weather. If I am only looking to do fair weather day sailing, will just GPS and back up paper charts be sufficient? Will also consult Eldredge prior to the trip for those days I am on the water.
OK first, Westbrook marinas. You can find some others via google, but you might as well just tie up at Brewer's Pilot's Point:
Brewer Pilots Point Marina, Westbrook CT
First rate service and they also have marinas in Old Saybrook and Greenpoint, NY. They are literally everywhere in this area. You might save a few bucks elsewhere if you look around.
You should be fine with the GPS and paper charts plus Eldridge. Note that your handheld GPS will eat batteries, so have plenty of spares and know how to change them quickly while underway. It may not have built in charts so you will want to load in waypoints to help you along. You won't want to be converting lat and long from the GPS to your charts, it's too time consuming, especially if you are singlehanding. Stick to Garmin in the GPS... the very best IMHO. The one I linked would be great because you can buy the charts from Garmin to load into the unit, and it just does everything well.
Be sure to have some good binoculars and a hand bearing compass might also come in handy.
Make sure that chartkit from Defender includes the waters around Shelter Island. I am pretty sure it does, but just make sure before you buy.