We've all been where you are right now. I remember going down to marinas
, walking the docks and not being able to tell one boat from another and being so frustrated! My father is a lifelong pilot and got me started in sailing. There are a ton of similarities between flying and sailing, so I think you will pick it up pretty fast. I'm not a pilot but I've done my fair share of flying in his Cessna and I can tell you the main difference between aviation and sailing is in aviation if you make a mistake you are dead in seconds but in sailing you have hours to think about it!
The post about Beth Leonard's book is a good one but might be a bit ahead of where you are starting right now. I would also suggest you pick up John Vigor's "The Seaworthy Offshore Sailboat
." He is extremely knowledgeable and never takes himself too seriously. Also, Don Casey's "Inspecting the Aging Sailboat
" will help you look at boats with a professional eye.
I also strongly recommend you spend serious time on yachtworld: if it isn't listed on Yachtworld it probably isn't for sale
. All brokerages list their boats on this site from around the world. Set different parameters and see what kind of boats come up. Look carefully at the specs and age of the boat and then the price
. After 6 months or so, you will be able to pull a boat up you are interested in and guess the price
within 10% or so. Then you will be ready to enter the market.
Best of luck. We look forward to hearing good news from you.