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My wife, my nine-year-old daughter, and I had been swimming for nearly an hour, circumnavigating a reef off a Bahamian island with the rest of our ten-person group, when our guide, Mia Russell, treading water, waved us over. “Guys,” she said in her singsong South African accent, “there’s a bunch of barracuda following us. Maybe twenty.”

I dipped my head underwater, and sure enough there was a line of the silvery, torpedolike fish stretching back into the shimmering aquamarine curtain of liquid as far as I could see through my goggles. “If they get too close, I just give them a bop on the nose,” Russell said cheerfully.

I wondered how I felt about this. I had seen plenty of barracuda before, but not in such numbers. In my rational brain, they weren’t threatening; barracuda often trail divers and snorkelers out of simple interest. My wife and daughter’s presence, however, had put me in a state of man-dad hypervigilance, with my limbic system on primordial high alert. Only later, while trawling through the internet, would I see words like “rarely” and “loss of tissue” crop up in conversations about whether a barracuda might mistakenly insert you into its food chain.

The battery of barracuda (yes, en masse they are called that) soon shifted course, and we were left to our languid strokes. Scrolling below us was a mesmerizing, diaphanous panorama of rainbow parrotfish and blue angelfish darting in and out of the reef. A sea turtle munching sea grass on the ocean floor put us at ease again.

Later, swimming close to shore, our lone little swim-capped group—we never saw any other swimmers—passed a low-slung yacht bobbing peacefully in the afternoon breeze. A woman in a Lilly Pulitzer dress, roused from cocktail-hour serenity by our presence, sauntered to the deck and asked, “What on earth are you doing?” It seemed a not unreasonable inquiry.

A year or so ago, I was looking to break what had become a sort of household impasse. These days my idea of a good trip is one where I collapse on the floor of a hot shower in my sweat-stained cycling jersey, beer in hand, after a punishing day on the bike. My wife would rather collapse into the chair of an art-museum café, petits fours in hand. My daughter splits the difference: she seems equally tempted by a spa visit with mom as a surfing lesson with dad.

What unites us is that we all prefer an active holiday. We like to come home feeling not rested but in need of rest. I wondered if there was a way to avoid the often inevitable feeling that a family vacation is a series of desires curtailed and compromises made, in which everyone wins by somehow simultaneously losing. (“Why yes, honey, I would love to take you to that fetid microbial sump that you call a water park, as long as you agree to go with us to this fascinating exhibit of post-Soviet conceptual art.”)

I wondered if I could get the satisfaction of accomplishment that came with my bike trips without the guilt of taking a vacation from the family. But cycling was out. My wife and daughter weren’t ready to go whizzing down Tuscan roads in a peloton.

I tried to think of something we could all do and enjoy doing. One afternoon, as I waited for my daughter to finish her weekly swim class, it dawned on me: swimming. My daughter, trained by her anxious parents since the age of three, was clearly competent. My wife seemed to enjoy churning out breaststroke laps whenever we found a pool. And I relished being in the water, although in the past few years this had mostly been on a surfboard. But you don’t forget how to swim, do you?

For a while, I had been vaguely aware of the growing popularity, largely in England, of what’s called “wild swimming.” Boosted in part by books like naturalist Roger Deakin’s iconic and a flood of subsequent swimming-changed-my-life memoirs—from to to —Britons were increasingly returning to long-neglected lakes and rivers, partly for a spot of exercise but mostly just for the unmediated joy of the experience. Meanwhile a growing number of swim-specific tour operators had emerged, offering trips in places like Croatia and the Maldives. These are like bike tours but in the water, with daily swims of varying distances (often depending on winds and other conditions) broken up by meals and supported by a safety boat, there to replenish swimmers with sugar (gummy sharks were popular in the Bahamas) and keep an eye out for watercraft that might cross our path.

I got in touch with , an operator based in the UK, and after making sure that everyone was cool with our daughter being there, we soon found ourselves on , one of the small Diapontian Islands off Corfu, Greece, in a myth-tinged corner of the Ionian Sea. (Odysseus was said to have been held captive by Calypso nearby.) The island’s tiny population seemed to consist almost entirely of old Greek guys wearing New York Yankees caps. Many Mathrakians, it turned out, had made their own odysseys—to Queens—before returning to live out their dotage on this quiet, pine-scented outcropping.

The trip was a revelation. Whatever uncertainty I’d had about the water—you will find “Corfu and sharks” in my browser history—or my desire to swim through great swaths of it immediately evaporated as we entered the warm, clear, ultra-buoyant sea, watched over by Russell. We would swim twice a day, sometimes hugging the shore, sometimes embarking on crossings of deeper, rougher channels. One day we swam two miles to our hotel from a tall, barren slab of rock our guides called Tooth Island that beckoned mysteriously on the horizon. Sometimes we would swim in and out of coves, looking for colorful fish or elusive crustaceans, exploring tiny, secluded beaches. Midday we would repair to the taverna for a Greek salad. At night we ate fresh fish, drank bottles of Mythos lager, and played Bananagrams.

Nothing you can do in nature is as immersive as ocean swimming. “You are in nature, part and parcel of it,” wrote Deakin, “in a far more complete and intense way than on dry land, and your sense of the present is overwhelming.” Our affinity for water is natural, Lynn Sherr writes in Swim: “We were fish ourselves hundreds of millions of years ago.” Our bodies are mostly water; our blood courses with salt.

Pool-trained swimmers, writes Leanne Shapton in , can find open water discomfiting. You can rule the pool, but your dominion does not extend to the sea. Winds slow progress, while the pitch and yaw of waves can wreak havoc with a swimmer’s stroke, even making them seasick. There is a need to constantly orient yourself. Looking down, you sometimes lose the contours of the known world. “I’m used to seeing four sides and a bottom,” Shapton writes. “I get spooked by the open-ended horizon, the cloudy blue thought of that sheer drop—the continental shelf.” Not to mention what one source in her book calls the “What the hell is down there?” factor.

SwimQuest’s founder, John Coningham-Rolls, says his company’s job is defined by what he calls the leap-and-be-caught principle. Generally, his clients are people who have dipped a toe in swimming and are interested in a larger challenge, but they’re unsure of how to go about it. “It’s ordinary people doing extraordinary things, safe in the knowledge that they are looked after in the elements,” he says.

In this other world, freed from the weight of gravity and the normal sense of time, people let go in more ways than one. “For some people, it’s a huge emotional breakthrough,” Russell told me. “Especially if you’ve had a trauma—it all comes out in the water.” Some people are simply trying to meet athletic goals, but for others something more transcendent happens. “It’s therapy, emotional release. I’ve cried into my goggles,” she says. “It’s this peace that overcomes you in the water, because it’s quiet. You’re floating. It’s comforting. It’s womblike.”

We were hooked. Which is why, less than a year later, we were in the Bahamas for another swim.

Our group’s base of operations this time was a large, tastefully decorated modern rental house on Great Guana Cay, a long, narrow islet in the Abaco island chain. It is known mostly for a golf-course community on one side of the island, which was built despite concerted opposition from locals and environmentalists and for being originally settled by loyalists—i.e., 18th-century Americans allied with England.

The ten-person group consisted entirely of women, with the exception of me and Guy Metcalf, a British swim coach who, along with Russell, was our guide for the week. This gender skew is common, according to Coningham-Rolls, who reminded me that “most swimming distance records are held by women.”

Apart from Russell, our guide from Mathraki, the group included Katie, an English pediatrician who lost her husband several years ago. She told me that he’d always sort of been the expedition leader in the family, and in trying to find her own path, she had come to the water. There was Patricia, a Frenchwoman in her sixties who lived in Chamonix and had taught herself to swim by watching YouTube videos. She exuded effortless glamour, had only recently given up smoking, and seemed to have a lengthy list of companies (H&M, Monsanto) that she was currently boycotting for various reasons. And there were Sarah and Ellen, a mother-daughter pair from the UK who had come to the Bahamas from another wild swimming expedition, a cold-water plunge in Sweden. Ellen, a student at the University of Cambridge, had set herself the goal of swimming somewhere other than a pool every day for a year.

Manning the sag wagon—a basic 26-foot fishing boat—was Troy Albury, the co-owner of Dive Guana, who normally takes visitors diving or snorkeling. He was jovial and sun creased, with a joke-riddled patter as smoothly worn as sea glass. As tends to happen in a small community, Troy had various roles on the island. One morning he was late because a tourist had flipped a golf cart and needed to be taken to a hospital. Another day, when someone struck my golf cart (long story), he suddenly materialized to sort things out. Like many people who live on islands, he wasn’t much interested in swimming, but he quickly grabbed a mask and speargun one afternoon when one of our group spotted a lionfish. He was out of the boat and back aboard, with dinner, in a flash.

As we headed out for our first swim, I tried to size up the group. SwimQuest does have training camps focused on competitive swimming—Coningham-Rolls had phoned me from Croatia, where he was leading a group of 13 swimmers on six-hour outings in 60-degree water. (They were preparing to tackle the English Channel.) But our week was billed as a holiday. You could push as much as you wanted, but the distance and pace weren’t meant to be punishing. Still, as someone who prides himself on a certain fitness, I like to know what I’m up against. Looking around at the present company, I decided I had nothing to worry about.

I soon realized my mistake, that I was making assumptions from my experiences with cycling and running that didn’t apply here. The polite older women, upon entering the water, transformed into powerful engines of hydrodynamic efficiency. I found myself falling behind, and not at all for lack of effort. To my surprise, my daughter, who I’d worried wouldn’t be able to keep up, was actually passing me. “Technique, technique, technique,” Coningham-Rolls had told me. Fitness only gets you so far in the water.

Unfortunately, my new passion for open-water swimming coincided with the fact that I actually did not know how to swim. The lessons I got at the Y as a kid were intended, as one swim coach told me, to keep me from drowning, not to help me move effortlessly through the water.

There were fundamental problems with my form that I didn’t even recognize as problems: I didn’t even know what I didn’t know. I often wondered, for example, why swimming laps left me more out of breath than my level of effort suggested it should. My problem—a common one—was that I was holding my breath underwater and attempting to both inhale and exhale when my head broke the surface. This is a recipe for hyperventilation. As the noted swim coach Terry Laughlin, author of , has observed: “One of the major differences between swimming and land-based sports is that breathing in the water is a skill, and a fairly advanced one at that.”

I had been trying to work out some of my issues before the Bahamas, but a lifetime of neurons firing in a specific pattern had left a serious imprint. Also, the lack of decent, uncrowded pools near me had been an issue. Russell asked how much I had been swimming since Mathraki. I said you could count the number of occasions on one hand. She shook her head.

As we gathered for a video review of my stroke, it was clear I had a way to go. My arms were not so bad, mostly because I had internalized the trick of dragging your fingertips along the surface as your arm prepares to enter the water. “Your right-arm recovery is really beautiful with that high elbow,” Metcalf said. Some lessons I had taken too literally. A long reach is generally prized in swimming, but I was overextending, my hand landing on top of the water, like a seaplane, rather than cutting into it at an angle, like a jumping dolphin.

The main problem was my legs. I had thought I could overcome other deficiencies by simply pounding the water on the strength of a lifetime of soccer conditioning. But I was kicking from my knees, not my hips. As my knees bent, my churning legs dropped down, creating serious drag—for a moment, Russell thought the video was playing in fast motion. All that frenetic motion was, as Metcalf noted, “pretty useless.” My spastic kick, Russell said, was not pushing the water back but down. “If you did the bend kick really fast,” she said, “you could actually go backward.”

Which is how I often felt I was going.

The days assumed a pattern: My daughter, who I had heard—with a mixture of admiration and envy—praised by the coaches for her “powerful kick” and “flexible ankles,” was typically up front with the faster swimmers during the four to five hours we were in the water. I would keep pace for a while but eventually find myself flagging. With incompetence masquerading as chivalry, I would swim near my wife, with her slower, steady breaststroke.

After the day’s swims were over and the others in our group flopped into chairs to read, I tried to regain my dignity by going running in the punishing, humid heat. On the fourth day this backfired. After a seaside lunch in Hope Town, I started feeling light-headed. What I thought might be food poisoning was actually sunstroke. Chastened, I lay in the boat drinking Cokes as Troy played me a selection of Bahamian rake-and-scrape songs and watched everyone else swim.

My travails in the water, paradoxically, were what I loved about the trip. For one thing, it seemed useful that my daughter saw her father—usually the authoritative figure giving her feedback on her running technique or answering all the questions in a trivia game—struggle to try and get better at something. For another, she got to hang with an intergenerational group of women united by a common passion. She had a genuine role model in the globe-trotting, acrobatic Russell, who had designated my daughter her apprentice “mermaid,” praising her for retrieving plastic from the water (“Ocean warrior!”) and coaching her on how to safely tickle a stingray on the chin, if you can call it a chin.

I also appreciated that the ocean was, for me, a big blank slate. On a bike, I had a precisely calibrated sense of my performance metrics (and a feeling of obligation to meet or exceed them). With swimming I not only had no sense of what good swimming times were, but I found that I didn’t care. I had no answer to the inevitable question, “What are you training for?” I simply wanted to get from one point to another, on my own steam, in a series of little quests that my wife and daughter and I could do together and commiserate about later. I wanted to see the beauty of the ocean while it was still there to be seen. I wanted not to sit on a beach but to swim to one. And when we did this—to visit the swimming pigs at No Name Cay—we caused nearly as much gawking as the aquatic swine themselves.

We’re already arguing about where to swim next year.

Contributing editor Tom Vanderbilt () profiled Jesse Itzler in ­December 2018.