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Raising a Family in Tight Quarters: Life on a Sailboat in Casco Bay

Cove Henry is three years old, and he’s a bit of a wild man. It’s mid-July in Maine and I’m with Cove, his big brother Kai, and their parents, Josh and Heidi, on the family’s sailboat (and summer residence) Tiny Bubbles II. Kai, the quieter and more contemplative brother, is sitting in an inflatable kayak, eating seaweed as the sailboat tows him through Casco Bay.


Cove is running around the cockpit, asking if he can go to the bow. Josh agrees but not before fastening a rope to Cove’s life jacket. Heidi tells me that usually they have jacklines set up. Jacklines are rope or wire guard rails that run from the stern to the bow of the boat. The boys attach to the jacklines with safety clips, so they don’t fall overboard. “They can move up and forward and we just clip ‘em in, but we don’t have the jacklines set up right now,” Heidi says as Cove, now securely tied to the boat, scampers to the bow and peers over the edge.

Cove and Kai are at ease on Tiny Bubbles II. The family has lived on the boat during the summer for the past three years. Heidi and Josh run the one-room schoolhouse on Cliff Island, six miles out to sea from the city of Portland. They live on Cliff in the winter but spend summers darting around the islands of Casco Bay. They’ll moor in Diamond Cove one night, and then move to a cove near Cliff Island the next.

Tiny Bubbles II is a small boat. For a family of four (soon to be five) it can get pretty tight on board. But for Heidi and Josh, this lifestyle comes naturally. The couple met in Maui, where they worked together at a school. After getting married, they spent the next three years sailing Tiny Bubbles I in the Pacific – from Hawaii to Samoa to Australia. “That boat was our home,” says Heidi, “We always said we need to do our golden anniversary after one year because it was a 24-foot boat, you couldn’t stand up inside, it was very small and we went totally engineless!” Josh and Heidi planned to live in Papua New Guinea, where they wanted to run a schoolhouse. But when they found out Heidi was pregnant, the couple (at the encouragement of their mothers) moved back to the continental U.S. to live close to Heidi’s mother on Great Diamond Island.

Sailing in Maine is vastly different than in the Pacific. The islands are close together, and docks in the Bay have amenities (like pump out stations and fresh water hoses) for recreational and commercial boaters. In some ways, life on Tiny Bubbles II is luxurious. The boat has a head (bathroom) and even a large bed under the bow for Cove and Kai. It is much more spacious than Tiny Bubbles I.

Cruising with Heidi and Josh, I struggle to see how life on a 28-foot boat could be all that comfortable. But making your home on the water in Casco Bay means that every nook and cranny on the uninhabited islands can be your backyard. When things get hectic on the boat, Kai will paddle his little brother into shore on the inflatable paddleboard, and the boys spend days exploring. Kai recently spent hours on Crow Island, by himself. I asked him what he did when he was alone there and he replied, “I built a sand castle… and I climbed on a rock and talked to the birds.”

“What did you say?” I asked.

“I said, ‘Do you want to play with me?’”

Written, produced and photographed by Galen Koch, 2014.