I'd probably hop to Marco Island and visit with Rocketman, then
head out and make sure you clear Romano Shoals, and make the open
water passage to the NW Channel. I have been through
Florida (crab pot) Bay, and popped out at Marathon, spending 2 days at Boot Key, then down Hawks Channel to
Key west. I liked Marathon and the eclectic
boating community nicely tucked in Boot Key.
If I ever make the ride back up towards Ft Meyers, I'd probably make the open water
passage.