Little Big Boat

With verve, skill, and confidence, this family reminds us that cruising small can be beautiful.

Calypso Bristol Channel Cutter

Small boat, big adventures: Calypso and her crew of four are right at home at Ship Channel Cay, Bahamas. Jeremy Waters

In A Midsummer Night’s Dream, William Shakespeare wrote, “Though she be but little, she is fierce.” Yet Shakespeare isn’t what came to mind just north of Vero Beach, Florida, the first time we saw Calypso.

“Man,” I thought. “That’s a little boat. Hey, look! They have kids! Wow, that’s a really little boat. With two kids? No way, José.” She hadn’t grown any the next time our paths crossed, three months later in the Exumas. But the more we got to know the Waters family, and the more miles Calypso and Osprey sailed together, the bigger that little boat got.

Calypso is a Bristol Channel Cutter, 28 feet of tough, seakindly sass and smarts. Johnny, my husband, and I had never had the pleasure of knowing one personally before; in fact, we’d sort of dismissed them and their kin as floating troll caves probably inhabited by small people with disturbing beards. But Nica and Jeremy Waters and their kids, Maddie and Julian, are anything but, and the lot of them—boat and family combined—blew all of our smug assumptions away like sea foam on a windy day.


Some 15 years ago and fresh from the altar, Nica and Jeremy, along with their beagle Toby, had sailed Calypso from Texas to the Bahamas, then through the eastern Caribbean to Venezuela and back, a journey of three years. They’d ended up in the Virginia foothills, moored Calypso in the town of Deltaville, and had a pair of kids. In the years that followed, they weaned their babies on Chesapeake Bay sunsets and weekend cruises, worked at their careers, and never considered the concept that they’d swallowed any hook. They were just waiting until they could go sailing again.

They debated buying a newer, bigger boat to better accommodate the four of them; they discussed a newer, bigger engine to replace Calypso‘s single-cylinder, hand-cranked diesel. But finally they came to the wisest decision, one so many would-be cruisers fail to reach. They didn’t need a tricked-out, expensive yacht (and the mortgage to go with it). All they needed was their simple, long-term intimacy with this little boat of enormous capabilities and the confidence to go.

They figured this time they had nine months—a narrow but precious window in which to introduce their kids to the life and to try it out themselves, as parents this time instead of footloose newlyweds. They quit their jobs, rented the house, and gave the two beagles, the cat, and the guinea pig to friends for safekeeping. They provisioned the hell out of the boat, then sailed to Florida, the Bahamas, the Turks and Caicos, the Dominican Republic, and back.


Their shower consisted of a dunk overboard followed by a cockpit soaping and a freshwater wash with a garden sprayer. Yet they were always impeccably turned out, and dinners aboard Calypso were elegant affairs with beautiful table linens, incredible food, and seating for all eight of us with room to spare. Sure, the galley was sort of small. But one of my favorite memories is of Nica and me washing dishes in the cockpit, our feet soapy and warm under the velveteen sky, the stars listening to our stories and laughter. Calypso was 28 feet to Osprey’s 45. But sailed well and fast, she rarely dropped far behind during passages, and then it was really only waterline length that made the difference. And she could skip through narrow passes between cays and reefs under stylish sail, nimbly wending her way to perfect little spots where we could never hope to go.

More than anything, Calypso and her masters reminded us that we’re out here to sail, not to motor; to explore, not to follow the herd; to reach for our common sense and savvy, not our checkbooks; to have faith in ourselves and in two big little words: Just. Go.

Osprey_ and crew are currently cruising in Panama’s San Blas islands._


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