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It depends on where in the Caribbean you are flying to.
Forever. There are no roads from the mainland to any of the Caribbean islands.
Mexico touches the Caribbean; hence time/distance is zero.
3 Months
That depends on where you're coming from, which you have not mentioned.
It depends on you internet connection and how busy the site is when you go to download. I've had updates take up to two hours and others just minutes.
About a month, depending on weather conditions.
It takes 2 weeks!
1 to 14 days or more
Normally it will only take a day for two...
four to five weeks, depending on the prevailing winds and weather
four to five weeks, depending on the prevailing winds and weather