I have made 2 trips in our Stream from DFW to the Florida Keys. Stock Island to be exact. IMO it's worth the extra 6 hours to go, if you have time. I stayed in West Palm and rode my motrecycle to Ft. Lauderdale. I rode on the A1A..all the way down.That was in 2006, before my Airstream days.
Be prepared when you get to Orlando to PAY Tolls...Per Axle. Unless you drive to Jacksonville and then go south. It's free all the way to Key West...but people drive like Idiots on that I-95. I live in the DFW area and honestly Noone else in the USA drives like them. Be careful and patient and you will do fine. Yes, I've been to NeW York, also...Trust me.
Again,..GO to the Keys. Stay at El MAR Resort on Stock Island,right before Key West. Boyds is no good,IMO. Eat at Hog Fish and The Rusty Anchor..not tourist traps,..where the locals eat.GO snorkeling in crystal clear water at Higgs beach in Key West. It's free..just buy your snorkel gear first. I spend HOURS in the water. Face down and butt up!...LOL There is a delaptated<sp> bridge that goes out about 200yds. No deeper than 8 feet. Beautiful. Just Beautiful...Then don't forget Duvall street. The Hemingway House. Mallory Square, live entertainers every night. The Atocha Meuseum,...Shopping....I love the Keys.
If you go that far,..you might as well. You only Live once...No passport needed and it is Paradise. Been going since 2005, either by plane,car or Airstream every year. Will continue to do it till I die. There is no place like it where you can pull a Airstream in the states. Carribean waters......Paradise.