I’ve only done it once, but taking a road trip from SWFL down through the Florida Keys is a magical experience. We even rented a Ford Mustang convertible for the trip so we could really just be tourists. Taking the Key West Express is obviously one of the better ways to get to the island, but driving the 113 miles down Florida’s Overseas Highway from Key Largo to Key West is something you need to experience.
Your first decision happens before you even leave Collier County. Alligator Alley is faster, but have you ever taken the Tamiami Trail all the way to Miami? I’ll admit, we cheated on that one and after making it most of the way we took 997 through Homestead to 1. If you just want to make a day trip of attractions on Tamiami Trail, there’s a bunch of stuff to do listed here.
There’s a lot of things you can do before you get all the way to Key West. Too many actually, to do in one day. So wherever you choose to stop on your Florida Keys road trip it’s going to be amazing. Stop at a random restaurant with a hand painted sign. Stay at a small hotel on a Key you didn’t even know existed. But most importantly, even though we already live in Southern Florida. Sometimes you just gotta stop and go be a tourist. There’s a reason so many people vacation here.