The Daddy Diaries
Two dads, five kids, four islands in southwest Florida. What could go wrong? From our March 2012 issue.

The Plan, at first, seemed perfect: Two dads and five kids enjoy a bareboat charter in southwest Florida. Five days of fun in the sun. Some real family bonding. Deep down, though, I knew The Plan would go wrong, maybe terribly wrong, and we’d have to improvise. But that’s what fathers are good at—improvising. At least that’s what I told myself 24 hours into the trip, as The Plan began to fall apart.
We were close-reaching south on the Gulf Intracoastal Waterway, just east of Gasparilla Island. To starboard, the blue-green inlet of Boca Grande Pass opened between two sandy spits, leading to the Gulf of Mexico. To port, shafts of sunlight beamed through the clouds, turning Charlotte Harbor into a Broadway stage of green shoals and brown shadows. Offering more than 200 square miles for roaming, the bay seemed ideal for a relaxing daysail with the kids, which shows how much I knew about sailing in the company of children.
We’d gotten a late start, and thunderclouds already loomed over the mainland, a fuzzy horizon of saw palmetto, mangrove, and slash pine three miles to the east. Normally, I wouldn’t sweat a summer squall, but the in-mast furling mainsail on our Hunter Passage 42 was refusing to furl. I was considering our options for shortening sail when my 8-year-old son, Ben, popped out of the companionway clutching his nose with both hands. Blood dripped through his fingers.
“I don’t know what happened. My nose just started bleeding.” He pinched his nose and lurched toward the stern rail to avoid staining the deck. When he leaned over the rail, his only pair of eyeglasses disappeared in our wake.
“Crap! I mean darn! Sorry, Dad.” He looked blindly in my direction, his world suddenly a blur.
Just then, my 6-year-old son, Jake, appeared through the companionway. “Dad, can you help me find my Pokémon cards?” Pokémon cards, as Jake will gladly explain, are like baseball trading cards, except the heroes depicted on each card are Japanese animé monsters with names like Giratina and Pikachu. Like most everything else in our household, the cards are forever getting lost.
“You’re on your own, buddy,” I told him. “The wind is picking up.” He looked at the sky and ducked back below before I could ask him for help.
I thought of asking the two 12-year-old girls in our crew, Isabella and her friend Kaylee, to help treat Ben’s nose. The two were lounging on the foredeck, comparing Glossy Bands, colorful bracelets they’d made the day before. They smiled and spoke to each other in a bubbly language that I, having no girls of my own, had no hope of understanding.
Jon Lemole, Isabella’s father, could have translated, but I didn’t dare ask. He was grunting over the Lewmar self-tailing winch that handled the mainsail furling line. He had a stranglehold on the winch handle, and the muscles on the back of his neck were a nest of rubber bands pulled taught, about to snap.
So. I turned to Evan, Jon’s 10-year-old son, who sat beside me in the cockpit. “Evan, could you go below and get some toilet paper for Ben?” Still groggy from lack of sleep, Evan was sitting like Buddha on the cockpit coaming and staring west, as if silently blessing the fleet of small fishing boats in the pass. Oblivious to the thunderclouds, Ben’s bleeding nose, or his father’s cage fight with a two-speed winch, he turned and looked at me curiously, as if I’d just asked him to paint the moon.
“How deep is the water up ahead, Mr. Nicholson?” he asked. “It looks pretty shallow to me.”
And all this time, the cockpit speakers were cheerfully booming Jimmy Buffett: “Boat drinks, boys in the band ordered boat drinks.”
As if the heavens couldn’t bear another Florida family-vacation meltdown, our worries disappeared as quickly as they’d come. The squall took a compassionate bend to the north, leaving white, puffy clouds overhead. Finesse and forearm strength cured the mast furler, a cottonball stemmed Ben’s bleeding, and Jake’s Pokémon cards materialized in his duffel bag. Ben tried out my reading glasses and stopped bumping into bulkheads. No gear was broken, no harsh words were exchanged, and there was no need to break the seal on the Flor de Caña rum stashed under the galley sink. Although not quite the Jimmy Buffett ideal, life was good again.
I passed Jon the helm and kicked back in the cockpit. As we reached toward the island of Cayo Costa, the waterway’s red and green markers aligned like highway signs, aiming toward a cloud that bore a striking resemblance to a young Bob Dylan—in his wild-hair days of Blonde on Blonde.
“Check out that one, Dad,” Jake said, pointing at the cloud. “It looks just like Pikachu.”
This was going to be fun.



