Sailing Firsts: A Long-Held Dream Comes True

Ken Perry recently dropped me a note to share an experience he’d just checked off his bucket list. For decades he’d dreamed of sailing a recreational boat to distant shores—by which he meant literally harnessing the wind in sails and exploring new coasts. During a 30-plus year career in the Navy, Perry commanded submarines and worked with nuclear power at depth, but he says that life beneath the waves was a different kind of seamanship than he now enjoys on an open deck heeling into wind and waves.

While he had skippered pleasure sailboats on occasion, frequent military relocations made boat ownership impractical. After retirement he and his wife finally had the time to pursue that dream: in May 2024 they bought a Hallberg-Rassy, moved aboard, and began sailing locally on the Chesapeake Bay. Finding the right boat also connected Ken with other owners and brokers who encouraged him to join the Salty Dawg Sailing Association, a nonprofit organization that mentors cruising sailors and organizes rallies that pair experienced sailors with those newer to offshore passages.

Ken signed up for his first long rally: a 1,700-mile passage to Antigua. He joined the crew of a Leopard 46 and, amid challenging weather and unforeseen conditions, helped that boat arrive first at the destination. He describes the experience as entirely positive, highlighting the practical support the rally provided—professional weather routing, on-call medical advice, 24-hour shoreside tracking, and the comfort of knowing seasoned sailors were available throughout the voyage.

Stories like Ken’s remind us that “firsts” are important turning points. For many people who love being on the water, the first time they accomplish a meaningful goal becomes a treasured memory and a foundation for more ambitious plans. For some, a first is bold and far-reaching—like a long-distance offshore rally into the Caribbean. For others, it can be more modest yet deeply satisfying: a maiden overnight to Block Island from Connecticut, a first offshore tuna bite, a trip down the Intracoastal Waterway to explore new harbors, or the day someone confidently backs a boat into a tight slip for the first time.

Firsts are not always about distance or speed. They can be the small, technical victories that make a sailor more self-reliant—handling a challenging sail change in squally weather, performing a confident man overboard recovery drill, or completing a solo day sail that once felt daunting. Each milestone builds skill and confidence, and the lessons learned contribute to safer, more enjoyable time on the water.

We’ve created a new department called “Firsts” to celebrate these moments and to collect the stories that teach and inspire. This section of Soundings will showcase reader contributions: short accounts of an initial achievement, the lessons learned, and any practical tips that might help others attempting a similar milestone. We’re looking for honest, useful anecdotes—whether it’s a sea trial that taught you the value of conservative weather margins, a training class that made all the difference, or a family cruise that became the start of a lifetime of cruising adventures.

If you have a first that changed how you approach the water—something that made you a better sailor or opened up new possibilities—please share it. Tell us what you did, what you learned, and what you’d do differently next time. Practical details and clear takeaways are especially helpful to readers who are aiming for their own firsts.

Ken’s note is a good reminder that it’s never too late to pursue a long-standing goal, and that supportive communities, proper preparation, and measured ambition make challenging voyages rewarding. Whether your summit is a long offshore passage or the simple but satisfying mastery of a docking maneuver, those early victories shape the way you experience the sea.

Jeanne Craig
Email: [email protected]

March 2025