Live in Wisconsin, want to cruise the Caribbean, have 30 days vacation a year...
If it were me, I would keep the boat you got which works well for you there, and I would fly to Tortola and charter for two weeks, split the boat costs with another couple of people.
Next season, charter in Granada.
Next season, charter somewhere else...
yeah, it's gonna cost you half of $ 5K a trip to charter for two weeks..
But what's it going to do pull a trailer from Wisconsin to Florida, leave yer car and trailer in Florida and sail to.........???? How far can you really get into the Caribbean before you have to turn around and start thinking about your haul back from Florida to Wisconsin?
You could settle on just cruising the Bahamas.....but in that case, the boat you have will work just fine for that.
Two Americans move to the TCI.
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