The short version: Fly into Fort Lauderdale, drive the Overseas Highway to Key West, spend three nights in Old Town and one last night on the beach. Skip Miami traffic, feed the tarpon, visit the Hemingway Home, sail to the reef and catch the sunset band.
In May I took my first vacation with myself in 16 years. I booked it in one day, on points, with nothing planned but the drive. This is that trip as a guide. It's built for wandering, not a schedule.
Every morning: wake up, have coffee, and ask yourself if you feel like water, wandering, eating or drinking. Start there.
Getting to Key West from Fort LauderdaleFlights into Fort Lauderdale cost fewer points than Key West, and the Overseas Highway is half the trip. Pick up the car and get on the Florida Turnpike early. I took US-1 through Miami and lost an hour in traffic. Don't be me.
Drive back up a day early and sleep on the beach, so there's no 5 a.m. scramble for your flight.
Stops on the Overseas HighwayRobert Is Here. A fruit stand since 1959 in Florida City, before the Keys. Get a strawberry-canistel shake and a slice of Key lime pie for the road. Robert Is Here.
Robbie's of Islamorada. Mile marker 77.5, bayside. Buy a bucket of fish and hand-feed the tarpon off the dock. Keep your fingers together. I almost didn't. Robbie's.
Seven Mile Bridge and Pigeon Key. In Marathon, watch the old railroad bridge run beside you, broken in places. Yes, that's the True Lies bridge. Pigeon Key.
What to do in Key West's Old TownWatch your street wake up before you go anywhere. Then walk to the two literary houses, ten minutes apart.
The Hemingway Home. 907 Whitehead St. Six-toed cats everywhere, one asleep on the bathroom windowsill. I cried here, and I was in a hurry. Hemingway Home.
Tennessee Williams Museum. Small, yellow, and worth the detour. I cried here too. Visit the museum.
FishMonster and Island Jane. Snorkel and sail from the Old Town docks. Three hours under sail with a stop at the reef. Solo tip: sit up front with the other solo travelers. FishMonster.
Sunset Pier. Behind Ocean Key Resort. Come for the sunset and stay for the band. You might end up onstage. I did. Sunset Pier.
Captain Tony's Saloon. 428 Greene St. The original Sloppy Joe's, where Hemingway drank, with a tree growing through the bar. Then follow the music. Captain Tony's.
I followed the music everywhere I needed to go.
Want a trip like this?I'll build yours, from the flight to the first sunset. Send one trip request, no phone call needed. Request a trip or book a Creative Burn if you're still deciding.