With your limited experience, I suggest you look into a trip to Washington
state and spend the summer fooling around in Puget Sound
. You can find cheap
boats here. You can buy a season State Park moorage permit
for about a $100 and camp all over the San Juan Islands
bouys and tie up to several docks and go ashore to explore, camp, crab fish
, salmon fish
, dive, etc. You can just put your anchor
down for free. You have light to moderate wind
conditions in the summer and can sail most of the time. You have alot of tidal action to deal with but you plan around it - come and go with the tide and make it work for you instead of against you. Your cost of living will be a far cry from what the Caribe will cost you! You can buy a trailer sailer you can pull with a medium sized pickup, enjoy your summer in the NW, then tow it home with you and put it on different lakes or tow it down to the Sea of Cortez
in the winter which is closer to where you live.
I've sailed all over the world in my life and I have as much fun here as I did in the Bahammas, Virgins, Med, Oz, China
Sea, etc, etc.
I spent 7 years in Alaska fishing
salmon on my troller. I'm going up on my 48' ketch
next summer. I've got a Nimble 20 that I'll rent to you and you can follow me around if you want. It's on the small side but I've camped in it alot - great little boat! Tuff, stable,sea worthy, unsinkable little boat. I put a bow sprit on it so I can fly 2 head sails
If I want. I honestly have as much fun with it as my 48'er.
You'd be miles ahead if you started this way. You would see some beautiful country, never be more than a day from land, grociery stores, drinking water
or free moorage/anchoring, no duty, no customs
, no entryfees, etc. You will learn to sail, navigate through tides & currents, visit many different islands, beaches ,etc., etc.
A good way to get some experience before you jump into more than you can chew and have a bawl doing it - The weather
can be challenging here but it's challenging everywhere I've ever been and in 40 years, I can say I've seen the elephant.
Something to think about. If you go for it, I'd be glad to help you out.