Setting Sail with Kids

"The sailing itch returned, and my wife and I decided it was time to raise sail again and introduce our brood to the dream."

By Josh Holloway

There are many romantic visions of family sailing life: sunsets, dolphins, children laughing in the rigging. There are fewer brochures featuring a toddler urinating on a carefully assembled brunch buffet. This is an oversight.

Cove and Kai enjoy a swing in the rigging of Tiny Bubbles II in the waters off Maine.

The Brunch Incident

“Josh, shut off the water!” my wife, Heidi, yelled up to me from the galley.

Huh? What water? I thought, as I turned just in time to witness our 1-year-old standing proudly in the cockpit, having repurposed himself into a fully operational fountain.

The stream arced gracefully across the entire brunch buffet and, for good measure, continued through the companionway onto my wife.

I reacted quickly, which is to say, not quickly enough. I scooped him up and redirected operations overboard, but the damage had been done.

It was at this moment I began to question whether long-term cruising with small children might involve certain... adjustments.

Before Children (A Simpler Delusion)

A little over a decade earlier, Heidi and I had set out on a grand sailing adventure as newlyweds. We were invincible 20-somethings, which is to say we had not yet gathered enough evidence to the contrary.

Our plan was to spend several years sailing the South Pacific from Hawaii to Australia aboard Tiny Bubbles, an engineless 24-foot sailboat. This seemed entirely reasonable at the time.

We followed the trades and wandered through Kiribati, Samoa, Tonga, Fiji, and Vanuatu—places that, at the time, existed primarily as dots on a chart and later as vivid reminders that we had no idea what we were doing.

People’s reactions ranged from “You’re insane” to “Yes, get it out of your system before you have kids.”

We took this as encouragement.

The Plot Twist

Three years later, in Australia, we realized Heidi was not feeding the fish because she was seasick.

She was feeding the fish because we were no longer kid-free.

This discovery significantly altered the long-term cruising plan.

Return to the Water

Fast-forward a few years and a couple of children, and we found ourselves living a mostly land-based existence on an island off the coast of Maine.

It was pleasant, stable, and entirely too sensible.

Eventually, the sailing itch returned. This time, we decided to introduce our children to the lifestyle—carefully, thoughtfully, and with significantly more provisions than before.

We purchased a cutter-rigged Shannon 28, Tiny Bubbles II, which included such luxuries as an engine, a head, and a galley—features we had previously considered optional.

Provisioning Like Optimists

My wife’s goal was simple: give our two boys (Kai, 4, and Cove, 1) a comfortable, well-fed introduction to sailing.

We went to Whole Foods and provisioned accordingly, which is always a dangerous place to begin any story involving the ocean.

We stocked creamed honey, lox, bagels, fresh melons, exotic fruits, juices, and a variety of other items that suggested we had learned absolutely nothing from previous adventures.

The Perfect Morning

We sailed to Monhegan Island and arrived just before dark after a smooth passage. The children were promised beaches, sticks, and other small humans in the morning.

Expectations were high.

The next day began perfectly. Heidi prepared an elaborate breakfast in the galley while I read to our youngest, who sat dutifully on his potty in the cockpit.

This arrangement seemed, at the time, entirely sound.

I turned away briefly to load a few items into the dinghy.

This was the critical error.

Moments later, the brunch buffet became a casualty.

Rapid Decline

“Aaaaaargghhhh, here!” I said, handing Cove down to Heidi while I attempted triage.

Bagels? Lost.
Creamed honey? Questionable.
Melon? Under review.

At that precise moment, our 4-year-old called down, “Uh, Cove’s doing something naughty!”

We looked below and saw a trail of small, unmistakable footprints leading across all of our bedding.

The source of the problem stood at the end of the trail, laughing.

There are moments in life when you realize the day is no longer salvageable. This was one of them.

Reality Sets In

Sailing presents certain logistical challenges. Laundry, for example, becomes an expedition.

Our perfect morning transformed into a multi-stage operation involving bagging contaminated bedding, transporting it ashore, and locating what can only be described as a dungeon with washing machines.

This, it turned out, was parenthood at sea.

What We Learned (More or Less)

We did not abandon the plan.

Over the next five summers, we cruised the waters of Maine, gradually adjusting expectations, refining systems, and lowering standards where necessary.

We now have three sons.

The third, Zev, is approaching potty-training age, which suggests we are about to revisit several previously learned lessons.

In the end, cruising with children is not the serene, postcard version of sailing life.

It is messier, louder, and considerably less predictable.

It is also, somehow, better.