[tevake]

Sounds like a fun trip. I suggest you do some shake down runs in the Tampa area. go over for a couple weekend, run the boat in that area, practice anchoring, docking, plotting on the chart. Do you have a GPS chartploter? that would greatly ease the navigational duties. Good ground tackle and a windlass make anchoring out a pleasure. And changes the nature of a boating trip greatly. Also an autopilot is a big plus for shorthanded passagemaking.

This would give you a chance to checkout the boat and systems. And get a feel for handling the boat. get an idea of fuel consumption, how does the boat do away from the dock over night, etc.
Also an opportunity to do some cruising in an interesting area that will be distant from your home waters.

Maybe invite some boating friends for a weekend there, this could lead to developing some interest in crewing with you for the trip.

Done with a captain will result in a delivery trip, a totally different experience than a cruise. Set yourself up to be comfortable doing it on your own, think road trip on the water.

Where are the pics?

Cheers Richard