Naples is nice, and you can keep your cat on the beach in front of Naples Hotel & Beach Club. I think if you spoke with them, they could let you park the trailer in one of their lots by the golf course.

Last time I checked, there was a spot to roll your boat through (about 10' wide) but you'd have to put the mast up on the beach.

If you're okay with a Getaway, most beach hotels have them ready to go for a rental fee... Maybe you could "knee-go-she-ate" a weekly rental rate?