Welcome and you maybe surprised by how many successful cruisers started about the same time are you are looking at. "Now" is always a good point to start.
To get on the fast track you may want to consider one of the many Vacation
/ Sail Certification
programs. Good way to get started the right way when you don't want to spend too long on the learning
curve and get the certifications often requested by charter
boat companies. Have a great vacation
in a wonderful location and learn more in a couple of weeks than you could ever hope to on our own in months.
Just in the past few days several posted indicated they were doing the vacation charter
out of US Virgin Islands
a great place to learn. Same is available in the BVI and Turks and even more distinct locations. ASA
is one of the larger organizations that has certified instructors located all over the US and Caribbean
. I did the classes
some 20 years ago and had a ball with the weekend classes
as I was working full time.
I would agree that sailing from Florida
may not be a great idea for a new sailor or at least it may be more uncomfortable than you may expect. Do consider possible purchase
in the Caribbean and use it as a base for a while.
Several years ago I bought a boat in Tortola and used it 4 to 6 months a year in multiple trips down and now I'm getting ready to fly down in December with a one way ticket and stay as long as it is fun. It is a really fantastic area and a great place to learn more about sailing in the sailing capital of the world.
Again welcome and let us know where the winds blow you... our paths may cross a few time!