Like another poster posted you can learn to sail in 20 minutes an the rest of your life gaining experience. Each time you go out you learn something new.
We had never been on a boat before we purchased ours. I was 63 then. We splashed her in July 08 with a friend on board. I backed out of the slip in Port O'Connor. Our friend raised the sails handed the wife the tiller and I killed the motor. She sailed out the ICW and half way to Port Lavaca. I finished the rest of the trip. So if a lifetime cowboy can learn to sail anyone can.
Don't get a big boat that takes a crew to handle. We have a 22'er that we are learning on. We also plan on taking her to Fla come spring. Nope not offshore but the ICW.
Make sure you have a reliable motor. Mines not and I hate it. Going to get a new 4 stroke before we head out.