Never chartered out of Key West or done any extensive sailing down that way, but did charter out of Fort Lauderdale from Fun in the Sun charters. It was our first bareboat trip, so just went from Ft Lauderdale thru Miami into Biscayne Bay down to Key Largo and back. We weren't pushing at all! It was a great first trip, but we would do much more if we did the trip today.

They do offer the option to preposition the boat or drop it off in Key West, so if Key West id the goal, you might want to check that out. I'd be more tempted to make the trip longer and just do the sail myself, but I really enjoy the sailing out that way, and the Gulf Stream gives you a nice boost on the trip back!

Anyway, its an option worth looking at. Good Luck!!


-Peter