Ken Perry dropped me a note recently, to share an experience he’d recently checked off his bucket list.
It had been a lifelong dream of his to sail his own recreational boat to distant places. “And by sailing I mean literally harnessing the wind in sails to discover new shores,” he said. During a 30-year-plus career in the Navy, Perry commanded submarines, harnessing the power of nuclear reactors for subsea missions, but, he said, it was not the same as heeling into wind and waves as a civilian on an open deck. And while he had skippered pleasure sailboats periodically, the frequent relocations for work made owning one impractical. But following retirement, he finally had time to explore on his own, so he and his wife bought a Hallberg-Rassy in May 2024, moved aboard and started sailing locally on the Chesapeake.
While searching for the boat, Ken met owners and brokers who suggested he join the Salty Dawg Sailing Association, a non-profit that educates boaters, often through rallies that pair old salts with newbies for offshore adventures. Ken signed on for his first 1,700-mile rally to Antigua, joined the crew of a Leopard 46, and then helped that crew arrive first to the destination in challenging conditions.
The experience, he says, was entirely positive. “It gave me the opportunity to make the trip with the benefit of professional weather support, on-call medical advice, 24-hour shoreside tracking, and the reassurance that seasoned sailors were within hailing range throughout the whole passage.”
Ken’s story, chronicles his trip with Salty Dawg, and it got me thinking about other “firsts,” those benchmark moments that have the capacity to move us in exciting directions.
People who love boats often like to talk about the first time they accomplished a meaningful goal. For some, that’s as bold as Ken’s mission to run 1,700 miles into the Caribbean on a pleasureboat. For others, the holy grail is a maiden voyage to Block
Island from the Connecticut shore, or a run out to the New Jersey canyons to hook that first white marlin. Others dream of making their way slowly down the ICW, testing their seamanship skills while taking in the unfamiliar shapes of new coastlines.
And then there are people who tick off firsts in an effort to become better boat handlers, one technique at a time. Who doesn’t remember the first time they backed into a slip like a pro? Others vividly recall that first heart-racing man overboard situation.
These experiences are the foundation for a richer life on the water. To celebrate those milestones, we’ve created a department called Firsts, and we’re opening the section to readers of Soundings for their contributions. I imagine many of you have at least one good sea story you can share about an event that served as a critical introductory lesson. Let’s hear it, so we can all gather some good and salty ideas for our own schooling.
Jeanne Craig
[email protected]
March 2025
