My understanding is that you can sail completely around the world in a small sailboat without ever being more than 2-3 weeks from a port of call. You check the weather forecast and leave for the next leg of your journey when you have a high confidence of a good weather window. And I've heard that pretty much no port will kick you out if you overstay your visa by waiting for safe weather (though you probably have to stay on the boat and not come ashore).
Also, at least in the US, typical boat insurance is very expensive if you want to have your boat anywhere near hurricane "areas" during hurricane season. People up here in the northern US like to take their boats down to Florida or the Caribbean during winter, but generally their insurance policy is null and void if they get there before Dec 1.