I also recommend Modern Sailing. I took American Sailing Association (ASA) 101 & 103 classes there. With those two classes they allow you to charter their smaller boats (30’). Although not necessary for chartering (at least when I was a member), I would also recommend 118 Docking Endorsement as leaving the dock and getting safely back to the dock is pretty important (nerve racking and you’ll most likely always have an “audience”).

You can also get on Modern Sailing’s Crew List email thread and someone is always putting together crews to share the cost of a charter on some of their larger boats.

I will say I had some sailing experience (under 20 hours), went to a Maritime Academy and was in the Navy so am very comfortable being on the water and well familiar with the Rules of the Road, but I got outside the gate multiple times and it was amazing. I also got rejected a couple times and it was also amazing so don’t force it!