I've been there and done that.
Before you jump into it, think: what will you do with your present possessions? Best answer put them into long term
storage before you sell them.
About sailing the
Caribbean, it'll are a year or two before you can safely do that.
BTW there is never enough room on a boat and you'll get rid of or store stuff.
Here is what I did and recommend.
Move to Fort Walton Beach, FL.
Find a Boatel, small place you can buy or rent with dockage. You need a home base, don't jump into
buying a boat yet.
Buy CHAPMAN and start reading. It is THE text boat on
small boat handling.
Join the Fort Walton Yacht club. Note the name difference. That club was the cheapest in the state. They had a great sailing/racing program. They had world class sailors as members. Great place to socialize and learn. Take the
Power Boat Squadron
boating classes.
ALL boats need
maintenance. Schmooz the people at West
Marine and the boat yards. Learn from those People.
Take a day or two each week and drive to all
marinas. You can find boats
for sale that are not listed where the people want to get rid of the. Beware, they will need
work.
I had fun living on a boat. You can have fun looking at all the boats out there. What size boat do you need?
Wind generators and
solar panels provide free electricity. Will you want a
water maker in the
Bahamas or a
refrigerator?
There are a lot of accessories for your boat to make you comfortable.
ME: I used the built in ice chest, 22 gallon
water tank, camping
stove and no
air conditioning. My 30 footer was too small for want you want to do.