You'll get a lot of opinions and advice here. But there are so many variables you will have to take each with a grain of salt
If you are new at this I would not recommend sailing FROM FL upwind to the Easter Caribe thru the Bahamas
. This can be rough sailing... upwind. Sailing the reverse direction is a down wind easy dry flat sail.
Sailing north and south through the eastern Caribe is pretty much a reach and you can fetch your destination
without tacking for the most part. But for example sailing into Point a Pitre Guadeloupe
will be upwind.
There are not very many marinas in the Caribe compared to the States and so anchoring
is something you'll need to master and rely on. You'll also need a decent dink and out board which becomes your life line to shore side activities.
There are any number of cruising guides
which you should have on board which will give you all sorts of useful information about each island, anchorages
and sailing directions.
Having lived in and sailed the Caribe for several years without a bow thruster or spending a single night at a marina or dock
I can say a bow thruster is not required.. but chain, a good windlass
is mission critical along with anchoring technique.
Refer is a nice luxury and most are 12v and so you'll need large batts and charging
source for them. AC is not necessary as the trades provide plenty of cooling
breezes. You'll want a bimini
of some sort of sun protection to rig at anchor
as well... Mission critical.
Unless you are requiring enormous amounts of electricity, you can make do with 12v, an inverter probably 2,000 watts, solar, wind generator
, high output alternator(s) and smart regulator
and not have to run a generator. They're noisy too.
I managed fine with an engine driven refer, large 8D batts and 110 watts of solar. I did run the engine between 1 and 2 hrs a day which charged the batts, got me in and out of anchorages
, cooled the fridge and produced hot water.
Sailing between Islands is a day sail (12 hrs) or less. But you want a reliable autopilot.
You'll have to maintain all the systems... be prepared... carry spares.
Look for a boat with a large and comfortable cockpit
Be careful... You'll have a great time.