I am a newbie to sailboats. I figure it is alot like learning to fly, seeing the sails are airfoils, so I am comfortable with the aerodynamics. I'm thinking I just need a few hands on lessons from an experienced sailor and I can pick it up. My question is this . . . I am looking to buy a home in Pensacola Fl for retirement in the next two years. I would like to sail as my retirement hobby. Do you sail boat owners recommend I start with an 18-23 footer to learn on, then sell it to buy a larger boat, or go with a 27-32 footer to learn on,? Here are some of the boats I have been considering . . .
Richard Bach once wrote that the reason Aviators like airplanes and sailboats is that both free you from the constraints of time. The airplane because it compresses time over large distances and the sailboat because you're simply not going to go very fast and you can't do much about it.
I raced dingy's in college and skippered and raced up to 44' boats in my time including racing J boats in Pensacola. Owned a 24' San Juan with another NFO at Whidbey for 8 years.
For my 2 cents you can learn a lot more about how sailing really works in a smaller boat but unless you're just going to day sail, which I enjoy a lot, or race a planing hull like an International 14 then go with something like a 22-26' boat.
Are you going to sail it alone? Get a roller furling headsail. Get an auto helm. In NPA sailing that single handed would be very easy most of the time. With an auto helm on ours I could even fly the Spinnaker myself in light wind. I also recall racing in the bay where we had to drop anchor to keep from being swept out of the bay there is so little wind. Get ready to motor when you need a Bushwhacker at the Sandshaker
Bigger is in many ways easier but if you're single handing you will need some power winches (or wenches your call!) and frankly as far as there sailing part it's not as much fun unless you're off shore on a good reach as a smaller boat.
Buy used! Tons of good boats out there no one uses anymore.