I took my US Sailing Basic Keelboat and Basic Cruising
classes at Sound Sailing Center in Norwalk CT. I highly recommend them. Looks like just under $4k will get you a daysailer
membership and the US Sailing Basic Keelboat class. Then you can sail their fleet of
Pearson Ensigns all year (they keeps a couple of boats in year round) as often as you like.
You would pay close to that just for summer dockage/winter
storage for most boats if you want to be a
boat owner. This way you can get your feet wet at minimal cost/investment.
https://soundsailingcenter.com/daysailer-membership/
https://soundsailingcenter.com/basic-keelboat/