Boot Key Charm | Cruising World

Boot Key Charm

During a longer-than-planned stop at Boot Key Harbor, in the heart of the Florida Keys, two southbound cruisers discover the locale’s unique charms.

boot key

Boot Key might be crowded, but it's full of Characters who make the cruising life rich.

Amy Flannery

Sailing into the cruisers haven of Boot Key Harbor, near the city of Marathon in the Florida Keys, I was stunned by the number of boats moored and anchored cheek to jowl. My first instinct was to turn and run. Why would anybody want to be packed into a harbor like airline passengers in the economy section?

We initially thought we’d be here for one or two days. That was before I wrapped the dinghy’s so-called floating painter around Mary T’s propeller while backing down on the anchor. Diving under the boat to cut off the line, my husband, Ken, discovered the propeller was bent. That led to closer examination of our engine, where we uncovered more problems. We’d been sucked into the Marathon Vortex, and we begrudgingly settled in.

Little by little, the charm points of the locale revealed themselves. The harbor offers superb protection and is connected to a beautifully run city marina, which provides weekly pump-outs. There are restaurants galore, many with long happy hours (noon to 6 p.m.) that include cheap eats. The community park has excellent sports facilities, and there are always fun and games in the marina’s tiki hut. But what really makes this place a magnet is the abundance of colorful cruisers.

One of the first characters we met was a retired diesel mechanic, Diesel Don Shuler. Don learned the trade working at his family’s John Deere dealership in Indiana, and he knows everything there is to know about diesel engines. In his deep, smoky voice and sensual Southern drawl, Don talks about engines like they’re works of art. He’s happy to come examine your motor and give advice for free. If you want him to get his hands dirty, his rate is ridiculously low, and he’ll teach you everything he knows along the way.

Don told us that when he turned 50, he was suffering from a number of injuries, including three broken ribs and various bodily sores resulting from explosions on boats. His cure was to sit in the sand about five feet underwater, breathing with the aid of a device called a snuba and watching the fish go by. “There’s nothing like warm salt water to cure all that ails one,” he said. Don’s a great raconteur and loves to expound on the joys of wearing a sarong and the advantages of composting toilets.

While Diesel Don is the engine man, Barnacle Bill DiVello is the underwater guy. Getting the bent propeller off our Morgan 38 required his expertise. At age 73, Bill is the oldest working diver in Boot Key Harbor. He cleans up to three boat bottoms a day — the same as his much younger counterparts. I asked if he was thinking of retiring soon, and he laughed. “I can’t. I just bought the lot next to our house,” he said. “I was afraid somebody might build a McMansion on it and block my view.”

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A trash clean up day was a success with cruisers.

Amy Flannery

When Bill returned to install our reconditioned propeller, he was covered in what looked like sawdust. Upon closer examination, I realized that the beige mass covering his wetsuit was moving. Millions of baby shrimp were crawling all over him! They came from the bottom of the boat he’d just cleaned. To add to my horror, he popped a few in his mouth and said, “Great protein.” Then he jumped in the water and went to work. In half an hour he had our propeller reinstalled and was on his way to acquire more shrimp.

Jolly Holly Freeman is another delightful figure in the harbor. Like Bill, she cleans boat bottoms, but she works off of her Sunfish, her preferred mode of transportation. Weaving through moored boats beneath an orange striped sail, with a captivating smile and blond dreadlocks, Holly adds a spark of joy to the harbor. She’s also a mover and a shaker. On the local cruisers net, Holly urges people to get off their moorings and go for a “Sail Away Sunday.” It’s a great way to get the cobwebs out of the sails and meet other cruisers by crewing on one another’s sailboats.

At age 93, Capt. Jack Burleson is the oldest live­aboard in Boot Key Harbor. He bought his first sailboat, a 27-foot wooden sloop, in St. Petersburg, Florida, in 1950 and named her Steer Clear. She served him well for 58 years while he explored the Bahamas and much of the Caribbean. His first trip to Marathon was in 1951. “It was a paradise,” he said, “with water so clear you could count the individual blades of sea grass. There was a beautiful lake with hundreds of migratory birds where the Publix grocery store now stands. You could wade into it up to your knees and pull out crabs for lunch!”

Ever the dapper charmer, Capt. Jack passes his days walking the docks dishing out good humor, flowers and seashells he’s painted. He has a razor-sharp wit and is full of tales, including some chilling ghost stories. The other day he spoke up on the morning cruisers net saying he’d lost his equilibrium and wondered if anyone in the harbor had one. I offered him mine, and he held on to my shoulder as we walked from his boat to the restrooms. Last I saw him, he was using a grocery cart for his equilibrium, which he prefers to a walker or cane. He smiled at me and asked if I’d like a ride.

Everyone in Boot Key Harbor is living the dream, but Cory Young and family came to it quickly and pursue it with gusto. Cory, 38, and his wife, Jessica, were both firefighters studying to be paramedics when Cory was diagnosed with stage III testicular cancer in 2008. It quickly metastasized to his lungs and lymph nodes, leading to a yearlong roller-coaster battle with the disease. He says in all seriousness that it was the best thing that ever happened to him. After winning the fight with cancer, he resolved to live life without compromise.

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Jolly Holly works hard in the harbour.

Amy Flannery

First the Youngs moved from Michigan back to Nashville, Tennessee, so Cory could resume his music career, singing and playing guitar with his friend Ty Thurman. During a family vacation to Marathon in 2011, Cory saw all the boats in Boot Key Harbor and proclaimed, “We can do that.” In two weeks they had bought their first sailboat, a Catalina 22, and learned to sail on a lake near Nashville. Three months later they bought an Endeavor 32, and the family of four moved aboard.

By January 2013 they had arrived in Boot Key Harbor, and within a year upgraded to a CSY 37, called Thin Line. No longer fighting fires, Cory and Jessica and their two kids are living life in the slow lane. Cory gigs at least three times a week with his buddy Ty, whom he convinced to move to Marathon. Jessica waits tables, and son Colby cleans boat bottoms and acts in the local theater. Daughter Peyton is a budding musician, and both the kids do their schooling online. The Youngs love the protection of the harbor and the community feel in Marathon, but they’re not stopping here. They aim to see the world by boat.

Hilary and Charles Badoian have been living in Boot Key Harbor aboard their catamaran, Ship of Fools, for five years. They welcome all newcomers with open arms and are largely responsible for the community atmosphere here. Event planners by trade, they recently organized a harbor cleanup. Hilary even added a scavenger-hunt component to make it more fun. Volunteers from the boating community were divided into teams and directed to different sections of the harbor to pick up trash. My ragtag team, on kayaks and dinghies, headed for uninhabited Boot Key. Small bits of plastic were as prevalent as organic matter on the ground, and thousands of larger pieces littered the mangroves. We finally had to stop picking the trash up because we couldn’t fit any more on our tiny vessels. In just four hours, the combined efforts of all the teams collected more trash than could fit in the dumpster provided by the city.

I hope the residents and legislators of Florida who want to enact laws restricting anchoring rights take note of this monumental effort on the part of sailors. Go Boot Key Harbor! I’ll miss this crazy place.

Amy Flannery is a filmmaker and lives aboard the Morgan 38 Mary T with her husband, Ken Kurlychek.

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