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."

January 16, 2018
Cove and Kai enjoy a swing in the rigging of Tiny Bubbles II in the waters off Maine. Josh Holloway

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

Huh? What water? I thought as I wheeled around and caught a horrific view of the problem. Our 1-year-old had hopped off his potty in the cockpit and was hosing down the entire brunch buffet, spraying a little additional pee on his mother through the companionway. I grabbed him as quickly as I could and directed the stream overboard, but the damage was done. Were we really going to make a go of the cruising life with gremlins aboard?

A little over a decade ago, Heidi and I set out on a grand sailing adventure. We were newlyweds, and invincible 20-somethings, so the idea of taking a few years to sail the fabled waters of the South Pacific from Hawaii to Australia aboard Tiny Bubbles, an engineless 24-foot sailboat, seemed fairly reasonable. We would follow the trades and frolic in the crystal-clear waters off Kiribati, Samoa, Tonga, Fiji, Vanuatu and other specks on the chart.


People’s reactions ranged from “OK, you two are nuts” to “Yep, get it out of your system while you’re young and kid-free.”

We both survived, and three years later, in Australia, we realized that Heidi was not feeding the fishies because she was seasick. No, she was feeding the fishies because “kid-free” was about to change.

Fast-forward a couple of years, and a couple of kids, to a mostly land-based existence, hunkered down on an island off the coast of Maine. All was well, albeit a bit chilly, but a sailing itch had returned, and my wife and I decided it was time to raise sail again and introduce our brood to the dream. We purchased a cutter-rigged Shannon 28 to serve as our summer digs. Tiny Bubbles II had all the bells and whistles our previous boat lacked, namely an engine, a head and a galley.


My wife’s wish was for our two boys (Kai, 4, and Cove, 1) to have a comfortable, well-nourished introduction to sailing, the likes of which we had never known. We went to Whole Foods and provisioned with the goal of utter decadence. There was creamed honey; lox with bagels and cream cheese; melons; exotic fruits and their juices; and other expensive tidbits to tickle the taste buds.

We moved aboard Tiny Bubbles II and promptly set sail for Monhegan, the quintessential Maine island. Arriving just before dark, after a smooth sail, the restless crew was eager to get some shore leave, but we tucked them in with promises of sand castles, pointy sticks, other little people and treats in the morning.

We all awoke early to get our perfect day started. Heidi busied herself in the galley, slicing the melon, toasting the bagels and lining the cockpit with a breakfast buffet to remember, while I read books to our 1-year-old as he sat on his potty on the cockpit sole. After finishing a book, I turned for a moment to put a couple of items into the dinghy, and that’s when our brunch buffet became a urinal.


“Aaaaaargghhhh, here!” I grunted, handing Cove down the companionway hatch to Heidi so I could attempt a salvage job.

Bagels? Terminal. … Creamed honey? I’ll try to pour the pee out of the jar. Can I just rinse the melon in some fresh water, Heidi?

At about that moment, our 4-year-old yelled up to us, “Uh, Cove’s doing something naughty!” We both peered down and saw the brown trail of footprints leading across all of our bedding — starting at a stinky pile on Kai’s berth and ending at the laughing 1-year-old standing on our berth.


Sailing presents certain challenges, and laundry is one. Our perfect day was transformed in seconds into a grueling ordeal consisting of bagging up all the bedding, ferrying it to land and lugging it to the laundry dungeon.

This reality was, well, parent­hood. We decided not to throw in the towel, and after five summers of cruising Maine’s waters, we’re ready to go full-time cruising again. Did I mention we have three sons now? And Zev, our third son, is ready to potty train.

The Holloway family is currently cruising the U.S. East Coast. Follow along at


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