When Jaana Penttila talks about freedom, you can feel the salt spray in her words. For eleven years, she and her husband Chris lived aboard their Swan 53 with their three young children, circling the globe slowly, chasing warm winds, new horizons, and the life less ordinary. It wasn’t luxury — it was life stripped back to the essentials: wind, water, family, and the endless unknown.
The Dream That Wouldn’t Sit Still
Jaana’s story began, as many do, with restlessness. She and Chris had sailed before children, loved the rhythm of the sea, and missed it fiercely once nappies and nursery routines took over.
“I remember sitting in this half-renovated house,” she said, “and just staring at the world map we’d stuck on the wall. Every day I’d look at it and think, we’ve got to go.”
So they made a deal — Chris wanted five years, Jaana said two, and they compromised on three. They never imagined it would stretch into eleven.
By July 2013, with the house still unfinished and three children in tow, Jaana booked one-way tickets to Grenada. Chris was horrified — but one frantic month later, he handed the house keys to tenants, boarded a plane, and joined his family on their new floating home.
Learning the Boat and the Balance
Those early months were spent in Grenada’s marina, getting to know their boat and their new life. “We were just learning how not to drown the one-year-old,” Jaana laughed. The Caribbean was a good classroom — gentle seas, friendly sailors, and constant repairs. “Everything breaks on a boat,” she said, “but it’s an easy place to fix things.”
Soon they were wandering north through the islands, Cuba stealing Jaana’s heart with its beauty and warmth. “It was magical,” she said. “Oppressive politics, yes, but the people — so generous, so alive.”
Then came Colombia — a planned short stop that turned into a full year. “We met this Scottish helicopter pilot who invited us for roast dinner,” Jaana laughed. “And that was it. We stayed a year for the Sunday roasts and the community.”
A Floating Village
It was in Colombia that Jaana realised what made the cruising world so special. “No one ever asks what you do for a living,” she said. “They just ask where you’ve been and where you’re going next.”
There’s a shared spirit among sailors, a quiet code of helping hands. “If someone’s sick, everyone offers medicine. If something breaks, ten people come over to help. It doesn’t matter your age or background — you’re just part of the same tribe.”
That sense of belonging would carry them through the hard times ahead.
Peru: Bureaucracy and Bird Mess
After a stop in Ecuador — where their boat almost drifted away while they were ashore — the family sailed on to Peru. “I’d read all these horror stories,” Jaana admitted. “I was terrified.”
Her fears weren’t unfounded. They were trapped aboard for days while officials sorted paperwork, unable to go ashore. Local sailors rowed over with food, wine, and kindness, but bureaucracy reigned. “Every form cost money, every signature needed another payment,” she sighed.
When they finally got permission to leave, they returned from a trip to Machu Picchu to find their boat plastered in bird droppings. “We spent three days scrubbing,” she said. “I nearly cried.”
Eventually, when new bribes were demanded, Jaana lost patience. “We just left,” she said. “Sailed out without papers during a regatta. I thought — we’ll get to Easter Island and figure it out there.”
Nine Days Without Sleep
It took two punishing weeks to reach Easter Island. The autopilot failed halfway, forcing two-hour steering shifts around the clock. “It was the hardest thing I’ve ever done,” Jaana said. “Nine days of helming, feeding kids, and trying not to fall asleep standing up.”
When they finally arrived, they accidentally anchored with their mainsail still up. “Everyone was watching,” she laughed. “They thought we were professionals — we were just exhausted.”
Their illegal arrival soon caught up with them — nine Chilean officials and a sniffer dog came aboard. But instead of arresting them, they stamped their passports and welcomed them to Chile. “I cried,” Jaana said. “It was such a relief.”
Pitcairn and the Vanishing Boys
From Easter Island they sailed to Pitcairn, home to descendants of the Bounty mutineers. With cliffs instead of beaches and only 40 residents, it felt like another world.
One day, her two sons disappeared. Panic set in. The island’s lone policewoman — on a quad bike — eventually found them halfway up a cliff near Fletcher Christian’s Cave. “They were drinking coconut water, totally fine,” Jaana said, still shaking her head. “But that drop… if they’d slipped…”
Pitcairn, she said, was magnificent and terrifying in equal measure — wild beauty balanced on the edge of danger.
Polynesia to the Pacific Edge
From Pitcairn they sailed to French Polynesia, where paradise came with a hefty price tag. “It was stunning,” Jaana said, “but Tahiti felt uneasy — too many people hanging about, too expensive.”
Further afield, on the island of Huahine, they found joy again. “There were about twenty kid-boats,” she smiled. “Our children had friends, freedom, and laughter. It felt like a big floating village.”
From there, the family carried on to the Cook Islands, Samoa, and beyond — battling winds, tangled anchors, and the constant edge between adventure and risk.
Storms, Sharks, and Small Miracles
In Suwarrow, a remote atoll, their anchor jammed under coral. Chris dived down with only a quarter tank of air and freed it — barely. “He popped up too fast,” Jaana said softly. “For a second I thought I’d lost him.”
Moments like that etched deep lessons: how fragile safety can feel, how quickly calm turns to chaos. Yet the rewards — empty lagoons, volcanoes, laughter under the stars — outweighed the fear.
When the World Stopped
By the time they reached Australia, COVID-19 had swept the globe. They found themselves marooned in Sydney for two and a half years. “But really,” Jaana said, “we couldn’t have been stuck in a better place.”
Australia’s kindness carried them through — even down to a borrowed car that opened a new chapter of friendship. When borders reopened, they sailed north again, hugging the Great Barrier Reef, dodging crocodiles, and finally reaching Darwin — only to find the tides impossible and the heat relentless.
Then, at last, Indonesia opened. They pressed on to Thailand, navigating quarantine rules, endless tests, and eye-watering costs. “Alice was screaming during the COVID swabs,” Jaana recalled. “It was awful.”
New Shores and Hard Decisions
Thailand brought calm. James, the eldest, started school; the younger two joined a small local classroom. For the first time in years, the family lived ashore. But as wars and economies shifted, so did their finances. With routes through the Red Sea unsafe and insurance impossible, they made a heartbreaking choice — to leave the boat in Malaysia and return to the UK.
Now, Jaana says, she’s learning to live on land again. “It’s hard,” she confessed. “I feel shackled — paying bills, council tax, insurance. I just want to be moving again.”
Still, her story is far from over. “We’ll find our way back,” she smiled. “We always do.”
About Jaana Penttila
A lifelong adventurer and sailor, Jaana spent eleven years living aboard a Swan 53 with her husband and three children, voyaging from the Caribbean to Easter Island, Pitcairn, the Pacific, and beyond. She now lives in the UK, planning her next chapter — one that will no doubt include the sea.
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