It's never to late to start!! I was visiting Friday Harbor (San Juan Islands) and it hit me like a bag of bricks..Well I was with my girl having a glass of wine watching the sail boats sailing away in the distance...I'm 42 and I'm ready to start my journey... Where do I start!! Lessons are first... I want to travel the world is for sure!! So I would need to find a sailboat that I will live while planning my trip and can handle blue water!! A boat that I could easily handle with ease??? A 40' boat is what I would like and of course I don't have ton's of money...So what type of boat should we get??? Used of Course..ha..ha..ha.. Any suggestions would be wonderful!!
The standing joke in my family is that we learned to sail on Youtube.
Seriously, watching videos there and on Netflix is a good place to start. Youtube has a lot of videos done by people that are out there sailing. There are a lot of people that video their day to day logs. That will give you an idea of how things will be. Read a lot of books. There will probably be a lot of people chiming on with suggestions - listen to them. There is a LOT of knowledge on this site.
To start with we bought a cheap little 26 footer - one that was in good enough shape to be safe, but that wouldn't break the bank if we sank her. We had enough insurance to pay for what we might break, too. We sailed her for about eight months and loved every minute. We sold her for what we paid and bought a 31 footer. Sailed her to the islands a few times and loved her. We ended up with a 36 footer that seems to fit us well.
We started small and cheap in the event that we might discover that we hated sailing. That way we wouldn't be out of pocket a lot. We really knew that we were going to love it, but didn't want to take any chances. Something else that I had not counted on is that the wife fell in love with fishing in the process. She has a passion for it now that is almost crazy. I have developed a passion for sailing and the mechanical/electrical side of boats, so things worked out well.
If you are going to take your girl out, start slowly. Let her get used to sleeping on the boat at the marina. Get up early and fix her breakfast. Make it "her" time, too. Take her out to a calm place on a calm day, sail a bit, then drop anchor in a calm cove. Her first experiences will stick with her! Then work your way into a more active sailing adventure. But we're getting ahead of ourselves here. You have to learn first, right?
It'll be nothing but fun, and you have come to a good place here to get started.