The short version: I booked a solo trip to Key West on points and a whim, a week out, with no plan. I flew into Fort Lauderdale, drove to Mile 0, snorkeled, sang with a band, got a tattoo and cried on the Seven Mile Bridge both ways. If you've been waiting for permission to take a trip with yourself, this is your sign.
Jimmy Buffett wrote "A Pirate Looks at 40." This is A Queerdo Looks at 44. If you want the practical version with the route, the stops and the stays, read the Key West solo trip guide. This one is the story.
Why I booked a solo trip to Key WestI had a few days off and an itch to see the sea, and I was stuck on where to go. AuDHD paralysis is pulling at nothing. Then it popped into my head: Key West. I could fly round trip out of Milwaukee for 28,000 miles to Fort Lauderdale, and the drive down the causeway alone would be worth it.
I hadn't planned a trip for myself in 15 years. I am not an itinerary person. I'm a wake-up-and-figure-out-what-I'm-starting-today person. I didn't have a single thing planned, and I didn't tell anyone but my partner Dalton. I just went and started posting.
Tuesday: Mile 160 to Mile 0The 6 a.m. flight out of Milwaukee went through D.C. and landed in Fort Lauderdale just after noon. Then a rental car and Route 1 south. I lost time in Miami traffic and should have taken the Turnpike sooner, but the Seven Mile Bridge made up for it. I especially loved seeing the spots where the old bridge broke, where they filmed True Lies.
I stayed at Alexander's Guesthouse, Room 11: roosters, a porch with rocking chairs and a pool at dusk. On Duval Street I realized Duval wasn't for me, so I took the side streets and found a little shop called Lost Boy Creations. It was the first place I went and I went back four times.
Wednesday: the booking mistake that made the tripI'd asked the front desk to book snorkeling for Thursday. They booked it for Wednesday by accident. So I did the Hemingway House first, then went sailing.
There were about ten people on the charter and half were couples. I sat at the bow with the two other solo travelers and we bonded over three hours on the water. One of them, a painter and tattoo artist from Peru who lives in Denver, is now a friend. I snorkeled for the first time, over schools of yellow jack on the only living coral reef in the continental U.S. That night at the Sunset Tiki Bar I was asked up on stage to sing with the band.
Thursday: long legs and a tarot readingI bought my first swim brief and wore it to the beach, a little family-ish, and decided I didn't care. I have long legs and I was going to show them off.
At sunset in Mallory Square I got a tarot reading with two new friends from the hotel. Right before it, I saw a call for new board members at the Brady Street Business Improvement District. I told the psychic I have so many ideas and a hard time moving on any of them. She said, "Just take action." I joined that board.
Friday: you gotta start somewhereI got a tattoo of the Key West Mile 0 sign, the one at the end of Fleming Street, at a shop that had been open a week. Mile Zero is the marker for everyone, because you gotta start somewhere. The bartender from happy hour started crying when I showed her.
Then I drove north with the Atlantic on my right and the Gulf on my left, crying again on the Seven Mile Bridge. I'd made more friends in a week than in years. I took Card Sound Road out and stopped at Alabama Jack's for an early dinner, which I'd do again.
Saturday: what changedI woke to sunrise over the Atlantic from a hotel room in Fort Lauderdale. On the way to the airport I stopped at a leather shop in Wilton Manors, walked in nervous and walked out in a tank top, welcomed. It got me thinking about the kind of space I want to build at home.
Something changed in me on this trip. I felt seen in a way I never have, because I allowed myself to be. I did not expect to take the first vacation with myself in 16 years and find parts of me I didn't know existed yet.
What I'd tell you before your own solo trip* Leave room. The booking mistake, the side street and the empty hour made the trip.
* Sit at the front of the boat. Solo travelers find each other.
* Say yes to the stage, the shop and the stranger's invitation.
* Go home slowly. Landing is the hardest part, so give yourself a day.
Want a trip like this?I plan solo trips, weekends and big escapes day by day, and I book them with you. Free to ask.
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