Planning on doing the Key West Poker Run. Any suggestions on where to secure parking for my truck and boat trailer?

Reach out to any of the good shops in South Florida but I would start with Brand X in Pompano.

http://www.bxpmarine.com/

There is parking at Haulover Park but I have heard some shady stories over the years.

What about parking for truck and trailer down in Key West itself.

If I do the run this year, I will have someone shadow me down with my truck and trailer and then pull it home from there.

Last year we dropped our trailer at Key West Harbor Yacht Club which is on stock island. They have a forklift and little area to spray down your boat for the haul home.