Sailing Key West

A trip to Key West proved useful yet frustrating to research three things for Let’s Go Sail. But the scenery and the culture are Paradise as advertised.

We found all manner of weirdness in architecture, restaurants, animals and of course boats. The biggest boats are the cruise ships, in this case the Seven Seas Explorer, getting ready to weigh anchor for the next destination. A mother-and-daughter team watched as the crew loosened the dock lines so they could throw them in the water. From there, a mechanical winch zipped the lines up to the bow. As the captain sounded one long horn, the ship slowly drifted off the bulkhead as stern thrusters pushed hard. Eventually the ship turned and headed into the sunset. Outgoing vessels slowed and stood back to give plenty of leeway. Within seven minutes, the Seven Seas was history, over the horizon.

Always looking for a change of venue or second location, Key West proved ideal for year-round climate, breezy sailing every day, and millions of tourists to draw upon. The drawbacks remain daunting. At least three comparable day charters by 6-pac captains already exist at the town docks, and numerous schooners and day sails add further competition.

Hurricanes pose the biggest risk. At the first warning, people rush to evacuate by car, which is a 150-mile trek back down the Keys to Miami. As the storm closes in, more people flee, jamming the Keys Highway to a crawl. Drivers run the risk of not knowing when the hurricane will hit. During Irma, they were blasted worst at Marathon than Key West, a dubious irony for sure for those escaping the tip island.

Irma hit Key West hard, tossing ships everywhere aground. One shop owner showed where the surge rose three feet on Duval Street. “It was a ghost town, without electricity or drinkable water. Nothing glamorous about it. Worse, it drove off business for weeks and months.”

Meanwhile the captains had to run their sailboats to hurricane holes somewhere. I never did find out where. The marina at Oceans Edge seemed to lie in the lee, but the very name of the place tells you it’s exposed to the east fetch. Dozens of magnificent yachts lie in sturdy concrete slips.

Pelicans flock in the afternoon for the remnants of fish guts from the day’s catch at sea. They perch on the bows of nearby boats and swoop down for the spoils. 

The most magnificent boat was a Fountaine Pajot catamaran called Pegasus. As a couple beat back and forth among the slips to learn the helm, their grown children waited for it dock in a slip. Their daughter said, “It’s 40 feet, brand new, the very first in America of its kind. They’re going to charter it out.”

I pressed her gently for the cost. “Between $1.4 and $1.6 million.” The couple backed the Pajot nicely into a slip that sells for $1 million. Across the way, an old fishing boat had a sign for sale at $175,000 but the slip alone cost another $475,000.

Which leads to another hindrance about venue. Slips are prohibitively pricey. God knows what they are downtown, but five miles south of town, where we were, I found a marina next to Oceans Edge called Stock Island Yacht Club. A girl at the ships store showed me a brochure quoting $47 a foot plus tax per month. That would cost Let’s Go Sail $19,200 a year, which is six times my current rate in Virginia. That make sailing Key West daunting.

Bottom Paint

My second quest involved finding the secret bottom paint that has eluded sailors forever. Along the town docks, I got differing opinions about various ablative or soft paints. One skipper said he uses anything by Interlux, “the more copper the better.” Another swore by Trinidad, another liked Pettit.

A captain on a 36-foot sailboat said, “I put five coats on every year, but the bottom still develops slime.” A grizzled schooner captain was blunt. “I used to own the Fury tourist fleet, up the street. I tried everything. It’s all shit.”

A diver at Oceans Edge Marina took a deep breath and answered, to my surprise, “Hard paint works well, actually. And it lasts longer than soft because it doesn’t wear off.” But it can’t be painted atop ablatives. “Right, you’d have to sand all of that down to the hull.”

Prop Paint

The final quest proved equally dismal. The bottom paint for props differs from hulls because hulls require ablatives that slough off over time in a proscribed way. Props need hard paint that won’t “sling” off. Our hotel lay across the street from a prop shop. I walked in and around and never found anyone, but I found other experts at the nearby Stock Island Marina.

Mechanics worked on giant outboards, with outdrives torn out and engines under repair. One row of three boats comprised 10 engines. A woman at the service shack said nothing worked. “First of all, you hit bottom too soon and the sand takes the finish right off. It’s very shallow around here, and unless you know the waters you’ll run aground. So no, nothing works.” At least for those who sail Key West. Virginia might be better with cooler waters. 

But one of her technicians said he had heard of success of a prop gel that goes on with a spatula and never really dries. “It turns rubbery and resists growth, but you may need someone with experience to put it on correctly.” I looked it up, and the directions said to spread the stuff on and then later repaint it. Sounds very gooey for a prop.

As I explored Stock Island Marina, I found the only beach anywhere short of Mile Marker 1, in town, or Smathers Beach near the airport. It’s part of the membership of the marina club. Sailing Key West makes this perhaps the best beach of all.

Two seafood fishing plants on Stock Island consume dozens of acres of magnificent waterfront. They have been serving the seafood industry for decades. Shrimpers and other fishermen dock their bots there and have service bays close to the road where they can work on their nets and lines. They turn their catch over to the owner, who pays them on the spot and processes the catch immediately for air freight out of nearby Key West Airport. “The only problem with that,” a nearby bodago owner said, “is that the bulk of the shrimp and tuna fly to China, and no one is flying to China these days because of the Coronovirus.” 

Other fingers of Stock Island got bought up so trailer parks will give way to  exotic resorts. A friend of mine who was stationed here years ago was surprised that the previously seedy island has any future. I explained that Key West proper has been bogged down with traffic and development. “Yeah,” he said. “It was cool when the gays discovered Key West, but then the redneck crackers from the Panhandle came down and ruined it.” 

Key West is nothing if not eclectic. It has more pirate flags than American flags. The Conch Republic motto, “We seceded where others failed.” Stock Island has more cats than most places, where dogs usual predominate. Have you ever seen a cat on a boat? This bizarro pickup sits permanently parked at a waterfront bar.

Photos of Ernest Hemingway are everywhere. He did some of his best work here and was assisted or encouraged by his wife Martha Gelhorn. His routine was to write in the morning, fish in the afternoon and drink at night. All within walking distance.

One night we used our membership at Kingsmill Yacht Club for reciprocity access to Key West Yacht Club, where we enjoyed a delightful dinner. The club was founded in 1938, just five years after the worst hurricane in history. That took moxie. 

Let’s Go Sailing Key West

Check rates and pick a day for a sailboat charter. See reviews on Trip Advisor.