The Daddy Diaries

Back to Nature
The next day, as we caught the ebb tide out of Redfish Pass into the Gulf of Mexico, my parental instincts returned from their weekend in Vegas, shocked—shocked!—at what they found. Horror of horrors, the kids were having a blast! This was not part of The Plan.

In our delusional scheming before the trip, Jon and I had imagined hours of fun—sure. But we also talked about creative ways to weave lessons about navigation, natural history, and biology into the trip. It didn’t seem like such a crazy idea at the time.

“Maybe next time,” I told Jon. With the stubble of a beard and circles under his eyes, Jon was looking ragged—like he needed a vacation. I wasn’t sure if he even heard me. “Cheeseburger in Paradise” was blasting through the cockpit speakers and the kids were singing along: “Big kosher pickle and a cold draft beer!” This, it seemed, would be the extent of their onboard curriculum. Bad daddies.

The steady southwest wind that had blown all week petered out after noon, so we motored the last few miles into Boca Grande Pass, past the historic lighthouse and museum on Gasparilla’s southern tip—another “to do” item that never got done. Within half an hour we were snug at the dock at what became my favorite stop on the trip, Useppa Island.

Trying to ease my guilt, I gave each child a sheet of notebook paper and asked them to list at least five facts that they’d learned on the trip. To my surprise, they liked the idea. The girls paired off against the boys, and the game was on.

Useppa Island was the place for a treasure hunt. For centuries, the island was an important center for Calusa culture, and the 50-foot-high shell midden stretching almost the entire length of the narrow, two-mile-long island left no doubt what was on the menu most nights.

A pathway through orchids and tropical fruit trees runs along the top of the shell ridge, and Key West-style vacation cottages line the path, each with a broad porch overlooking the water. At the highest point, a three-story Victorian hotel, the Collier Inn, rises next to a championship croquet court.

Built in the early 1900s, the inn is named after Florida pioneer Barron Collier, who used Useppa as a vacation retreat for his wealthy friends who liked to fish, dine, and whack golf balls around a rough-hewn course. The walls of the rustic Tarpon Bar, a classic varnished-pine and polished-brass watering hole overlooking the marina, are hung with portraits of these early snowbirds—dressed in their Sunday best—teeing off or battling with tarpon.

Today, the privately owned island is for members only, but guests can arrive on daytrips by boat, and nonmembers can arrange an introductory stay at the island cottages or inn.

Sipping a mojito poolside while the kids played, I tried to imagine what the place was like in 1961, when the resort—at that time abandoned—swarmed with C.I.A. agents and Cuban exiles training for the ill-fated Bay of Pigs invasion.

Although interested in the tales of Calusa warriors and C.I.A. spies, the kids were most impressed by Useppa’s wildlife. Manatees grazed in the surrounding sea-grass beds, osprey nested in the channel markers, and endangered gopher tortoises burrowed in the open fields between cottages. The treasure hunt had barely started when the Fisher Queen, Mango Girl, and Ol’ One Eye discovered another natural attraction: Tiny horseshoe crabs hatch each summer in the soft mud along the shore.

I collected the kids’ lists that evening as we enjoyed steaming plates of Jon’s famous spaghetti (one of the big advantages of having a true-blooded Italian on board, even if he is a Yankees fan). Their findings were impressive: the coordinates for the lead beacon to Boca Grande Pass, the arrangement of markers on the I.C.W., the names of 23 species of birds they’d seen on the trip, nine species of fish found in the local water, and a variety of mango trivia (from Mango Girl, of course). My parental instincts breathed a sigh of relief.

On the last night, Jon and I finally put a dent in the Flor de Caña and reflected upon the trip. We talked about sports, and kids, and music—and then tentatively about Rita. We both agreed she was probably happy to be watching our clumsy attempts at parenthood-under-sail from another place.

“She liked the idea of being outdoors,” Jon said, smiling, “as long as she could go home to her own bed.”

The next day, we returned to the Southwest Florida Yachts charter base, hopped in the car, and headed home. The fullness of our lives aboard Fortuitous receded, as if it had been a strange and funny dream. Our five-day charter didn’t deliver any miracle cure, but it brought—if only for a moment—a bit of peace and clarity.

That night, while tucking Captain Thunderfoot and Ol’ One Eye into their beds, I no longer worried about my big plans falling apart. I just wished time didn’t fly so fast. Peering out from beneath a mound of stuffed penguins, otters, owls, and bears, Ol’ One Eye seemed to read my mind. “Dad, can we do that again sometime?” he whispered.

I smiled, swelling with pride, and let the words sink in. “You bet.”

“Good,” he said, with a sigh. “But next time—let’s bring mom.”

Former Cruising World senior editor Darrell Nicholson is the editor of Practical Sailor magazine. At last check, Jon, Evan, and Isabella Lemole had three sailboats in their growing fleet: one Sunfish, one Optimist, and a Catalina Capri that was once owned by Jon’s grandfather.