Really, if you never have sailed before, it's hard for me to help you other than giving you this advice: find a sailing school, join a club, find some weeknight beer can racing. Learning on my 50ft boat is just not the best idea. Can it be done, sure, but it would not be my first option. If you insist, I'll take your money, book a 3 hour sail and I'll explain.
Do you know any serious golfers? Do they take lessons? Of course they do. That's how we get better. When you dock is it a pleasant experience? Do you have anxiety when anchoring or wonder why other sailboats seem to be going faster. Do you want to take the mystery out of changing your own fuel filter or raw water impeller? These are all things that shouldn't make your day on the water worse. Offshore, overnight, ICW....you can do it, I can help.
I can't tell you how many calls I have had and heard "I want a boat, I need to take my wife out and have a good time" Or "We have a 30fter and I want a 40 but I don't know if we can handle it"
They don't just let you take these things for a ride...I encourage everyone to charter before buying if they are uncertain.
Picture: Jim and Cindy used to be powerboaters, they wanted to give sailing a try and came out for 3 hour sail. Fast forward to today - they own a Beneteau 423 and have completed a trip to the Bahamas. I often joke they are my most accomplished students, but they really did it on their own. They just needed a little nudge!