I worried about my back. It went into spasm just a week before the scheduled start of a three-day trek through the Ten Thousand Islands on the Florida Everglades’ Wilderness Waterway. Even sitting at my computer for long stretches aggravated the tightness in my muscles. How would they hold up to hours of tough paddling while seated in the cramped cockpit of a kayak, followed by nights separated from the hard ground by nothing more than a thin sleeping pad?

I worried about the weather. The waterway, on Florida’s extreme southwestern edge, is just what its name implies: a watery tropical wilderness without shelter or even dry land for miles at a stretch. A wind storm or, heaven forbid, lightning would be no small problem.

I worried about the permitting process. The campsites on the 99-mile-long waterway, part of Everglades National Park, are widely spread and have limited occupancy, allotted on a first-come, first-served basis. But the earliest you can reserve is 24 hours in advance, in person at the park office, so it was impossible to plan the trip before it began. Given that adverse winds and tides could turn a four-hour paddle between campsites into a desperate 12-hour struggle to make dry land before dark, putting together an itinerary could be a high-stakes gamble.

I worried about provisioning. The sea kayaks we’d be renting were narrow torpedoes of boats, with tiny forward and aft storage compartments that would have to hold tents, sleeping gear, clothes, food and five gallons of water per person.

I worried about bugs. My old friend Gregg, a Miami native, had just been out in Big Cypress Swamp and reported the bugs as homicidal. When I asked him for an anti-bug strategy, he responded, “Suicide.”

My wife, who most emphatically was not coming on a trip where the nearest plumbing would be miles away, focused her anxiety on reports of escaped pythons, whose population had begun to explode in the ‘Glades. I knew that, among all the potential dangers we might face, constriction by giant snakes ranked in the “not going to happen” category. Far more realistic was the possibility of getting lost. The waterway is short on man-made markers, and the endless chains of mangrove islands and bays create a labyrinth, with jigs and jags in the apparent coastline that make the difference between a pass and a dead-end impossible to distinguish even up close. I was planning on navigating with a two-decade-old sea chart and a compass, a task made more challenging still by having to study the chart from the cockpit of a moving, wind-and-wave-buffeted kayak.

In the days before departure, I lay awake strategizing, woke up realizing that I’d left something essential off the provisions list, spent the day obsessively hunting for tips in online discussions among waterway vets.

Seem like a lot of anxiety over a “vacation”?

No doubt, but I’ve learned that often the trips that require the most effort deliver the greatest rewards. This trip, a self-propelled journey into one of the world’s great remaining wildernesses, could become a nurturing memory for years to come. To be taking it with two old college friends I’d last traveled with in 1973 and with my 21-year-old son, Sam, who had miraculously consented to sacrifice part of his spring break to paddle with a gaggle of geezers, upped the ante to once-in-a-lifetime opportunity.