Wookie
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I second all this. Towing is a big deal that far. I towed my 21 footer from Tampa to Key West and blew 3 tires. The boat spent the night on alligator alley while I searched all over Weston for spares.How many wheels on each side of the trailer? I'd get that many per side, ie, if two wheels on a side, carry two spares- minimum. Reason is, whatever flattens the first one will likely flatten the one behind it; now you're stuck until you get one tire into a town to be fixed if you only have one spare. That may not be easy on a evening or weekend.
I would also think about getting another wheel for the truck. Same reason, and if your truck is disabled, you can't just get a tow truck with a boat attached.
Extra lubricants and coolant for the truck.
A full shop/ trained expert checkout wouldn't hurt.
Do you have a trailer lock?
I would invest in a good boating safety course focused on the ocean, I'm sure Wookie could recommend one, and there could be a Coast Guard Auxiliary near you as well. The local Coast Guard station (Islamorada, IIRC) may be able to help as well. They may be willing to help by inspecting your boat too. Ask Wookie, he probably knows the most of anyone on this board about that area.