Hi,
There're three major geographical divisions to LI sailing, as you probably already know. North Shore, South Shore (mianly the Great South Bay) and East End, which is the Peconic Bays, Shelter Island Sound, Gardiner's Bay, Block Island Sound, etc etc. Steve Bellavia knows more about the East End than I; I'll leave that to him.
I bet "Bob T" can tell us about the North Shore, I'd sure like to know more, too...
As for the Great South Bay... the amazingly good thing is: you get 15 kts SW any sunny day unless the larger weather pattern overrides the SW seabreeze. The one tiny drawback is the very healthy waters support a huge population of eelgrass, which gets uprooted by the powerboats, and drifts around the bay in clumps, some of which get so big you'd swear you could walk on. The bay warms up quick in the spring, as it is very shallow, ranging from 8 inches to 18 or so feet, only getting deper near the channels leading to the ocean.
A bunch of us sail out of Heckscher State Park, field 7. The park is at the end of the Southern Parkway (use the Sunrise Hwy if you're trailering a boat - only the last mile of the parkway is open to trailers, that mile is called the Heckscher Parkway.)
Whichever is a good sailing day, some of us will be there this weekend... and as you might have read, Monday, weather permitting, is also under discussion. Stay tuned.
Why don't you come down for a ride on any / all of our boats, to help you get an idea which may or may not be for you? The H 16 is a fine boat, a boat which started the whole thing, or nearly so, the H 14 came before, and there were others around, too, but it was the Hobie line which became synonymous with the boom in catting. However, while many people find it satisfies them all their lives, others move to different boats, for different reasons. Sail around, find your preference early. 'nother thing good about H16; you can buy an old one cheap ($1000) sail it two seasons, and get what you payed for it if you sell it due to learning to like another kind of boat.
As for instructors, hell, just show up at Heckscher every weekend, we've made plenty of total newbies into competent, safe, *fast* sailors.
Just drop in at field 7 and use the secret code phrase, "Hi, nice boat." and we'll reply with the standard countersign, "Want a ride?" You should bring a bathing suit, a wetsuit if you have one, many of us carry spares.
Keep watching the forum, I'll try to post whatever I hear about sailing plans.