It is uncanny how the sea and sailboats offer the most unimaginable adventures and, in turn, education, one can ever experience as a human being. Some discover this right off the bat as a young child exploring shallow bays in a dinghy. Others spend their last hours, and dollars, sailing in a straight line for as many days as possible to soak up the grandure that is life on this aquatic planet.

Jesse Smith serenades his daughter with his Ukelele 500 miles from Virgin Gorda.

Jesse Smith serenades his daughter and his mother, far left, with his Ukelele 500 miles from Virgin Gorda.

I know three families who have come to this realization at mid-life and luckily for them, they have young children whom they can share their wanderlust. And these sailors have done what seems to be the hardest part in taking a grand adventure: they actually moved onto a sailboat!

One couple has spent years angling to actualize their experience as charter captains pre-children and re-explore the caribbean with their son and daughter. Another has found a life, they hope, will re-define their core reliance on each other and allow them to educate their children in an open and inspiring way. Yet another couple, spur of the moment, decided circumstances were ripe for an adventure and recognized the potential to create a family connection beyond almost anything you could accomplish on land.

I will write about their diverse stories. Each family comes from a very different socio-economical background and has different interests and approaches to navigating through life. And it is wonderful to watch those approaches unfold in their boat and homeschooling choices.

Now, I would like to share with you the spark, or baby steps of one of those families. Jesse Smith and Annice Kenan have chosen, or in some ways were chosen by, an 11-year-old traditional Gannon and Benjamin Schooner named Rebecca of Vineyard Haven. While their two young daughters transitioned into homeschooling last summer, Jesse completed a major refit of the boat’s hull and electrical systems. They had a brilliant shake down in Maine but friends and family were usually in the mix. Two weeks alone gave them a taste of family freedom. Then came the raucous fall reach to Bermuda and the Caribbean with wiley friends. Now the Smiths and the two other families, all well acquainted, are in the Caribbean attempting to avoid the temptation to swim all day, or think of a way to make a lesson plan out of all the wondrous natural and cultural glories that accompany touring and passagemaking.

l-r, Amanda Sparks (1st mate), Richard Feeny and Dave Fallon (cook), off watch in North Atlantic.

l-r, Amanda Sparks (1st mate), Richard Feeney and Dave Fallon (cook), off watch in North Atlantic.

In the images here you see the Rebecca of Vineyard Haven crew, one being Richard Feeney, a professional sailor and coach who is notable for his success with Tommy Hilfiger in the Extreme Sailing Series and running the education programs at the Herreshoff Museum. You’ll also see Tim and Dave Fallon singing a song they wrote one night at sea on Rebecca. Tim is a two-time ISAF team race world champion and owns a magnificent, engineless, 28-foot wooden catboat Kathleen.

Enjoy their inspiration and I hope you find your own. It’s all around in our sport. And it is addictive. When Tim and Richard returned from the delivery, they spent a December Saturday in 17 degrees match racing in Beetle Cats.

Tim Fallon (green sail) and Richard Feeny reach to the finish, 12/14/13, Sakonnet River.

Tim Fallon (green sail) and Richard Feeney reach to the finish, 12/14/13, Sakonnet River.