Dry Tortugas, Wet Weather, and the Art of Adjusting Expectations

Key West, you oddball paradise. Two miles by four miles of chaos, conch fritters, and questionable fashion choices. You’re so small that everything sounds close—until you’re actually walking in 85-degree humidity and realize “just down the road” means “bring water and sunscreen.”

I’ve somehow been to Key West more times than Miami, which feels statistically improbable given that Key West has almost no beaches and Miami has several—plus more air conditioning. Still, it has charm and chickens and enough eccentricity to fill a reality show. I keep coming back. I even think about braving Fantasy Fest someday… although I suspect I’d need both emotional and physical armor for that level of exposure.

This time Chad and I flew ourselves down in the Vision Jet—affectionately known as the baby jet—for a Southern Trial Lawyers Conference. I jumped at the chance to tag along because it meant I could finally visit Dry Tortugas National Park, which is only reachable by ferry or seaplane. I’m on a kick to visit National Parks because my friend Joe has inspired me. He’s currently trying to get to all 63. This summer he took a sabbatical and went all the way to Alaska for a month. – Goals! 

For the record, “tortugas” means turtles in Spanish. The “dry” part was added to warn sailors there was no fresh water. (Imagine traveling months at sea only to land on an island that’s BYOW—bring your own water.)

When we landed, another Vision Jet taxied in right next to us. For a moment, I half-expected to hear the Jetsons theme as Chad strutted across the tarmac. “Meet George Jetson…” played in my head while I wondered if Rosie the Robot was refueling somewhere nearby. That other jet had an internet Vision Jet Celebrity in it—there’ s like three of them and this was the least insufferable (according to Chad).

The skies looked grim, but optimism (and humidity) was high. We checked into the Opal Hotel, which sits conveniently near the Mel Fisher Maritime Museum—home to the legendary treasure from the 1622 shipwreck of the Nuestra Señora de Atocha. Fisher spent sixteen years searching for it, found $450 million worth of gold and silver in 1985. However he tragically lost his son and daughter-in-law in the process. Proof that treasure hunting is not a family-friendly hobby.

After gawking at the gold, we headed to the conference reception. The sunset was doing its thing—magical as ever—and I couldn’t help noticing that every speaker was from South Carolina. Clearly the current president, who is from South Carolina, just called his friends and said, “Pack your flip-flops, we’re going to the Keys.”

Dinner followed at A&B Lobster House, where Randy (also there to be a speaker because he is from South Carolina) and I both ordered lobsters, because what else do you order at a Lobster House?

Then came the rain. — When in Doubt, Find a Museum

Friday’s forecast: Wet. My plan: Denial because I had booked a jet ski tour of the island and I have never been on a jet ski. While Chad sat in his conference, I went exploring between raindrops. I’d already done Hemingway’s house on a past visit—his second wife’s uncle bought it for them, proving that marrying into money occasionally works out—so I went in search of something new.

First stop: The Audubon House. Built in the 1840s by Captain Geiger, who made his fortune in shipwreck salvage (which is exactly what it sounds like—profiting off other people’s bad sailing days). The house at some point hosted artist John James Audubon, so when it was restored in the 1950s, someone (Michell Wolfson) decided to mash up shipwreck décor and bird art. It’s an odd combo, but somehow it works. That’s Key West in a nutshell: confusing but charming.

Next: The Custom House Museum. A glorious red-brick building from the 1890s that now holds exhibits on local history and maritime disasters. The story that caught me was the explosion of the USS Maine in 1898, which sparked the Spanish-American War. I knew almost nothing about it, but now I want to read an entire book. Key West: come for the conch fritters, leave with homework.

By afternoon, the storms were in full drama-queen mode—lightning, thunder, and rain so heavy the iguanas were seeking shelter. It is unnerving when you can hear and see the lightning happening at the same time. Our jet-ski tour was of course canceled, but we did manage to find dinner at a cash-only restaurant where the Wi-Fi (and thus credit cards) were victims of the storm. Thankfully, Chad had hit the ATM earlier—always a girl scout! 

Saturday dawned with broken clouds and rising hope. We headed to Key West Seaplane Adventures, which operates two 1950s-era de Havilland Otter planes—basically Cessnas on stilts. Our pilot, Kris, appeared wearing flip-flops, which gave me pause until I learned he flies barefoot. Nothing says confidence like a pilot who doesn’t need shoes.

Once airborne, Jimmy Buffett played through our headsets as we skimmed 700 feet above turquoise water dotted with turtles. It was blissfully surreal—a mix of Margaritaville and Indiana Jones.

At Dry Tortugas, we explored Fort Jefferson, the largest brick structure in the Americas—16 million bricks, all floated over by boat. The fort was never finished because by the time they neared completion, military technology had already moved on. (Imagine spending decades building your dream home only to learn open-concept forts are out of style.)

We tried snorkeling, but the wind turned the water into a blender, so visibility was roughly one inch. Still, floating around a Civil War-era fort while fish swam by was worth it.

That evening we dined at Louie’s Backyard, which feels like eating on the edge of the world—if the world served Key Lime pies. We were told Jimmy Buffet had his favorite table there and lived and worked next door. We wanted to believe, so the truth of it didn’t matter.

Sunday morning, we loaded up the baby jet and headed home, hoping to make the Panthers game. The only hitch: our windshield fogged so badly from humidity that Chad had to stop taxiing, shut the plane down, and wipe it dry like he was detailing a 747 with a beach towel. Glamorous, indeed.

We made it home on time. My jet-ski dreams were dashed, but the seaplane made up for it, and Key West delivered its usual mix of eccentricity, humidity, and unexpected charm.