Everglades City is little more than a runway, Tamiami is a big airfield, which used to host some of Kermit Weekes' treasures but sadly no more... The main purpose for stopping there was to put on the life vests. Homestead Municiple airport (not the (ex?) airforce base) has an FBO I think, but we stopped to answer calls of nature! The AFB was still active then as we watched two pairs of F-16s launch. You get routed out to the coast after leaving Tamiami to stay clear of its zone. We just did a touch and go at Marathon.
Key West FBO is probably good, but we took a taxi into town and had a meal at a restaurant on the seafront. While you're at EYW, there is (or was) a Waco UP-7 you can joy-ride in - takes two in the front seat. Cost me $40 about 10 years ago for a few minutes and I think the second pax would have been included in the price.
The 500ft is excellent - haven't done that at MIA yet, but have at Palm Beach!
Naples can get a bit busy - we were doing circuits there on a Friday afternoon when just about every type of Biz-jet decided to depart/arrive, so we took the hint and scooted across to Marco Island and did a few more there.
Have a good time!