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Mr. Adventure: Lessons from Sailing School

Can you believe we had to learn a whole new language to keep our boat from spinning to who-knows-where?

Gary Hovland

I’m going to let you in on a little secret: The reason Mr. Adventure chose to leave his beloved New York and purchase waterfront property in Southwest Florida was so he could buy a sailboat. Cliché? No doubt.

It’s a fantasy many people harbor (ha!), sailing the beautiful blue waters of the Gulf of Mexico without a care in the world (or property taxes, or a mailing address, or houseguests). But while most of the people who’ve actually gone out and bought that sailboat are just looking for a few weekend escapes over the course of a year, I bought my property with the full understanding that someday soon technology will fail us and we will all be forced off the grid, unable to use our cellphones, refrigerate dairy or watch Hart of Dixie on the CW.

Trust me when I say that the power will go out—for whatever reason—and having convenient access to water for both fish and travel will be worth its weight in gold. (Good luck to those of you living on golf courses.) And as much as I’d like to just go out and buy someone’s used sailboat on Craigslist and sail to parts unknown—that would amount to suicide. After all, sailboats are to middle-aged men what ham sandwiches were to Mama Cass—a delicious idea that will ultimately break your heart.

 So I decided that in order to give myself the best chance of surviving the upcoming apocalypse, I needed call up the good folks at Offshore Sailing School and enroll in their Learn to Sail Five-Day Certification Program at the South Seas Resort on Captiva Island. (They also have programs operating in Fort Myers Beach and St. Petersburg—not to mention New York; Chesapeake Bay, Md.; and the British Virgin Islands.)

As hard as it is to believe (at least for me), you need to study and learn things in a classroom before you can take to open water and yell, “Thar she blows!” or whatever other colloquialism befits the sea.

There were five other future sailors sitting quietly when I walked into the room—a couple of Carols, a Catherine, a Tommy and a Bob. All from out of town—none with hooks or peg legs. Clearly amateurs.

Our instructor, Rick Hinman, a personable and tanned son of a gun, had a slideshow, a whiteboard and a model sailboat to help demonstrate some of the things we’d need to know before climbing aboard and hoisting up those fabric things that help the boat move when the wind blows. Turns out they’re called sails. And there are different names for each area of the sail—the tack, head, clew—and then the edges of those sails have other names (leech, luff , foot, roach).

But, of course, the terminology doesn’t stop there. It seems sailing employs an entirely unique language unto itself. You’ve probably heard of port and starboard (left and right, respectively), bow and stern (front and back), and things like booms and masts and keels. But, holy Jesus, there was not one crossover word from the English language as far as Rick was concerned.

You’re in irons when the boat gets stuck in the NGZ. To get out of irons, you must ‘back wind’ the jib and the bow will fall away from the wind, and off you go,” says Rick.

I’m sorry, what?

Prepare to gybe! Gybe ho!

Wait! I know this one! Is that a song from the Pussycat Dolls?

Ready about! Hard-a-lee!

“Speak English, you S.O.B.!” I didn’t actually say that out loud, but I thought it. Salty language is just part of being a sailor. Trust me, I’m a natural.

Ultimately, I got the gybe of it. Haha. See what I did there? It sounds like gist. Anyway, once I got the hang of making crib notes (Rick was fond of calling out our names in pop quiz fashion and I needed help), the ropes came out for tying practice. Now I’m not casting aspersions, but the ladies seemed much faster studies at knot tying than the guys. (Thank you, Fifty Shades of Grey.)

Just then, as the morning was coming to a close, three of us got the go-ahead to join Rick on what must be the best classroom on the planet—a Colgate 26 sailboat: shiny, white and awesome.

Though there was no master cabin, professional galley or teak-filled salon with iced buckets of Mr. Adventure-approved champagne, it was definitely better than Rick’s slideshow. And after we all slipped on our life vests and gloves (rope burns, ya know), we climbed aboard for adventure—anticipating the sparkling turquoise waters gently kissing our bow.

With a Carol on the tiller (the thing that steers the boat), Catherine on the main and me on the jib (something connected to a rope up front), we looked to be a right good crew. Within minutes we were greeted by pods of dolphin, manatees and loggerhead turtles and it was clear this course was way better than English Comp. 101.

But then Rick started talking that language.

“Prepare to gybe!”

Oh God. Is he talking to me? I’m on the jib. (I think.)

“Grab the halyard,” says Rick.

“You’ve got some luffing,” says Catherine.

“I do? Is that bad? And the halyard again is…?”

“The rope to your left,” says Rick.

“There are three ropes to my left, Rick” I say to the people in my head just before I grab the red one.

“Good choice,” says Rick. “Give it a good pull.”

“You’re still luffing,” says Catherine.

“Did you ever see Dead Calm?” I think to myself.

It was clear I was going to need a few more days of instruction in order to get my luffing issue straightened out. It seems sailing is a challenge for the uninitiated. There were three students and an instructor on that boat, and there was never a moment when we all weren’t doing something that seemed integral to making the boat move. If Rick, God forbid, had had a heart attack or fallen overboard, there’s a better than average chance that we would never have been heard from again.

Now that really would have been an adventure.


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