I know this isn’t the right place for this but there’s way more folks here than elsewhere.
I was hoping to do another BVI or Bahama trip this time, but got overruled.

Has anyone ever chartered out of Key West? I’m curious about pros/cons, suggested itinerary, etc.

Posting so I can follow...

Florida is bursting at the seams with tourists right now - we have never seen anything like it.

I know Dream Yacht Charters has boats - friends chartered this past December and had a less than stellar experience with the boat, unfortunately. It was not the norm of their experience with Dream.

Their pictures looked great - but I didn’t get the feeling it was something they would do again. No comparison to the USVI/BVI/Abacos from what I gathered.

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

We did some extensive research on sailing the Keys. From Middle Keys south, it appears that you have very limited mooring/good hold anchoarages. There are some slips available, but they are expensive. Heading to the Dry Tortugas would entice me (we've been there many times via seaplane) but you have to have great weather windows. We passed and sailed the USVI last month and are here in the BVI on our new cat now (and it was worth every protocol measure to get here).