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Most people who cruise even part-time aboard their boats are doing it in the later years of life, waiting until they have the time and means to make the lifestyle possible. 

But not everyone follows this script. One exception is the family onboard Cortado.

Born and raised in Indiana, far from the smell of salty air, Lynne Rey will freely tell you that living aboard a boat was far from a dream of hers. So how does this artist and mother find herself schooling two children and managing family life aboard a classic power cruiser?

Tony Rey comes to this boating life a little more organically, having grown up on Long Island Sound. Tony had an early start racing sailboats and enjoying summer cruises aboard his family’s boat. From that love of sailing came a career of racing sailboats professionally. The life of a professional sailor requires considerable travel. Over the years, Lynne and their oldest daughter, Sydney, traveled with Tony during some of his races, and Lynne home-schooled Sydney during those trips. When their youngest two children, Sophia and Oliver, were 10 and 8, Tony and Lynne thought it would be good to expose them to a broader world, teaching them in what would become known as “adventure school.”


Racing sailboats wasn't conducive for making boating a family experience for the Rey family, so they decided to buy a boat and live part of each year on board. The opportunity would give Lynne, Sophia, and Oliver a small taste of Tony’s life at sea, and provide learning opportunities that couldn’t be matched in any classroom.

With Lynne’s apprehension about open water and the restricted living space of medium-size sailboats, it didn’t take long to realize a comfortably sized power cruiser would be more suitable for their purposes. “I go seven knots in my day job, so I wanted a bit more speed and freedom," said Tony. "I wanted to share all aspects of the water with my family, including safety, fishing, navigating, co-existing in a small space, maintenance and cleaning. It has been much easier to accomplish all this without heeling over at 25 degrees!”

Around the harbor back home in Newport, Rhode Island, Tony and Lynne explored every type of boat imaginable. They found themselves drawn to the classic, aesthetic-forward styles, as they wanted a boat that was both functional and attractive. Classic Huckins cruisers quickly rose to the top of their list, and their search eventually took them to Florida to visit a 1973 Huckins Sedan 40. A family with two children close in age to theirs had restored her to Bristol condition.


Not only was she restored, but she was modified to suit a young family of four. The galley had been moved up to the salon level, which Lynne preferred over boats she had seen with the galley down. Two large bunks were added where the previous galley had been. The salon and galley opened up to a covered area leading to the cockpit. The boat also had a flybridge covered by a Bimini. The elevated helm platform meant a better vantage point to read the water depth in the shallow tropics, not to mention a great place for an out-of-the-way afternoon nap. Additional sleeping quarters and plenty of covered living spaces made the boat well suited to live aboard. The previous owner had also re-powered her with twin Cummins diesel engines. Tony and Lynne added a complete suite of modern electronics. 



The Reys began their new life aboard Cortado—which got her name from their favorite Spanish coffee drink. Over the first winter, they cruised from Jacksonville, Florida, to Key West and back, exploring and learning the ways of their new lifestyle. The long-range plan was to live aboard during the winter months and return to their home in Newport for the summer. The following winter, they aimed to venture a little farther, setting their sights on the Abacos in the Bahamas.


They spent most of the winter between Miami and Key West waiting for a weather window to make their crossing to the Bahamas. When the window finally arrived, they crossed over the Gulf Stream between Florida and the Little Bahama Bank, dropping anchor at Great Sale Cay. Working as a team, the Rey family agreed that the effort and wait were worth it. They then spent the following months exploring the Abacos archipelago.


The goal of their floating winter home was to expose Sophia and Oliver to different cultures and the inherent education that comes along with adventure. 

Of course, the uncertainties and obvious challenges are many. 

"Travel and adventure schooling isn't for everyone. It's not easy—and no, we are not on 'vacation'—but for those who are able to make it work, the rewards are significant. It's the passion for life, travel and our small family that keeps us going. We love being together ... growing, learning, changing and supporting each other.”


Living aboard has noticeably changed the Rey family. It is palpable. 

"We can feel the change in our ways and attitudes," said Lynne. "Our time in Florida and the Bahamas was a slow-burn balance of extreme beauty, quality family time and nature. We found it necessary to readjust our expectations in the areas of weather (largely unpredictable), school time, and overall pace.

“We're embracing an unfamiliar path and willing to take the risk associated with that. In the spirit of adventure, we are allowing ourselves to be vulnerable, try new things, meet new people, go new places. And we're happy. Could this educational path work for more families? I would say, emphatically, yes!”

The Reys' cruising lifestyle reminded me of the words of author and artist Debbie Millman, who wrote: “If you imagine less, less will be what you undoubtedly deserve. Do what you love, and don’t stop until you get what you love. Work as hard as you can, imagine immensities, don’t compromise, and don’t waste time. Start now. Not 20 years from now, not two weeks from now. Now!”

This story has been updated since its original publication date in Passagemaker magazine.