The Florida Keys season most visitors overlook...

...and why locals know the water is just getting good.

Author

Florida Keys Road Trip
May 26, 2026

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Date: May 25, 2026

Hey Keys lovers! Memorial Day may feel like the unofficial start of summer everywhere else, but in the Keys it marks the beginning of something better: quieter roads, warmer water, lower rates, and a calendar full of only-in-the-islands traditions. This week we're looking at the start of the "secret season," a 35-year-old duct tape boat race, and the wild story of a Key West fire chief who vanished into thin air.

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❓ Keys Trivia

Is Key West closer to Cuba or to Miami?

Answer at the bottom of the newsletter.

📣 The Mile Marker Roundup

⛵ Minimal Regatta: The 35th Annual Schooner Wharf Minimal Regatta took over the Key West Historic Seaport yesterday, with 20 homemade boats built from a single sheet of plywood, two 2x4s, and a roll of duct tape racing (and sinking) for glory. Read more → https://media.visitfloridakeys.com/duct-tape-dreams-set-sail-at-key-wests-minimal-regatta/

🐢 Lily J Goes Home: The Turtle Hospital in Marathon released "Lily J," a juvenile green sea turtle rescued after a severe boat strike, at Higgs Beach in Key West on Saturday to celebrate World Turtle Day. Read more → https://www.keysnews.com/news/local/celebrating-slow-smart-turtles/

🎣 The Catch Pro-Am: South Carolina Outcast won the 4th annual SFC "The Catch" Pro-Am tournament in Key West with six sailfish releases, while NFL running back Dalvin Cook swept the fun fish categories with a 29-pound blackfin tuna, 15-pound mahi, and 10-pound wahoo. Read more → https://sportfishingchampionship.com/news/26thecatchrecapkw

🚫 FWC Bans Export: The Florida Fish and Wildlife Conservation Commission unanimously voted to ban the international export of endangered and threatened marine life, following viral outrage over a manta ray collected in Marathon for an Abu Dhabi aquarium. Read more → https://keysweekly.com/42/fwc-bans-export-of-threatened-marine-life/

📅 Summer Events Announced: The official summer calendar is out, featuring Key West Pride (June 3-7 ), Coralpalooza (June 7), the Key Lime Festival (July 1-5), and Hemingway Days (July 19-26). Read more → https://media.visitfloridakeys.com/from-key-largo-to-key-west-a-summers-worth-of-festivals-event-traditions-and-america-250-celebrations/

🌴 Partner Spotlight

The Secret Season Just Started

If you think summer in the Florida Keys is just too hot and crowded to bother with, you're missing out on the best time of the year. Memorial Day marks the official start of what locals call the "secret season."

That's why a lot of long-term Keys visitors actually prefer June and July. The winter crowds are gone, hotel rates drop significantly, the water temperature hits a perfect 82°F, and the fishing is spectacular with mahi, tarpon, and grouper all in season. Plus, the summer event calendar is packed with festivals you won't find any other time of year.

If you've never experienced the Keys in the summer, this is the year to do it. The water is waiting.

🧩 Deep Dive

Split Rock / Destroyer Key

The island split in two by a WWII warship.

If you look at a satellite map of the backcountry waters about 3.5 miles west of Key West, you'll see a mangrove island with a perfectly straight, deep-water channel cutting directly through its center. It looks man-made. And it is, but not on purpose.

The island is historically known as Split Rock, but locals call it Destroyer Key. In the 1940s, the USS Amesbury, a heavily armored World War II destroyer escort that saw action at Normandy, was stationed in Key West to support the Fleet Sonar School. During a severe storm, the massive warship crashed into the mangrove island, becoming deeply embedded in the limestone and sediment.

When salvage tugs finally arrived to pull the ship free, the immense force of dragging the hull backward tore a deep trench right through the mangroves, permanently splitting the island in two. The Amesbury was freed, but sank a short distance away while still under tow.

Today, Destroyer Key is a popular "secret spot" for locals. The shallow turquoise water is perfect for snorkeling, floating, and bird watching. But don't try to find it yourself — the channel is nearly impossible to navigate without a local captain who knows the shifting sandbars.

Have you ever been out to Destroyer Key? Hit reply and tell us — we'll publish the best stories next week.

🕰️ Lore & Legends

"Bum" Farto: The Vanishing Fire Chief

In the 1970s, Joseph "Bum" Farto was the fire chief of Key West. He wore red leisure suits, rose-tinted glasses, and drove a lime-green Ford Galaxy with an "El Jefe" license plate. He also sold cocaine and marijuana from the bench outside his fire station.

In 1975, an undercover sting called Operation Conch busted him. He was convicted in February 1976 and faced up to 31 years in prison. But days before his sentencing, Farto told his wife he had "business in Miami," rented a Pontiac LeMans, and drove north. The car was found abandoned in Miami. Farto was never seen again.

The disappearance became legendary. "Where Is Bum Farto?" t-shirts sold out across the island (Jimmy Buffett even wore one ). Some claimed they saw him in Costa Rica; others said he was at the bottom of the ocean. His wife finally had him declared legally dead in 1986, but the mystery of the vanishing fire chief remains one of Key West's greatest unsolved stories. Read the full history here → https://www.mentalfloss.com/history/mystery/bum-farto-key-west-fire-chief-mystery

✅ Trivia Answer

Cuba, by a lot.

Key West is approximately 90 miles from Havana, Cuba, but about 160 miles from Miami.

Bonus fact: This proximity heavily influenced Key West's culture, architecture, cuisine, and history. Cuban cigar makers relocated to Key West in the 1800s, and the island's food, music, and architecture still carry strong Caribbean and Cuban influences today.

Until next week, keep your windows down and your watch off.

The Florida Keys Road Trip Team


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