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Seasons Change, Magic of Coastal Cruising Endures

DATE POSTED:October 14, 2025
two sailboats in fall Two cruising companions sail past autumn’s palette, savoring the season’s quiet magic before it’s time to haul out. Sonya Etchison/stock.adobe.com

I’m a displaced New Englander, which means I’ve always measured my sailing seasons not by the calendar, but by the feel of the mornings. In July, it was bare feet on a sun-warmed deck. By October, it was fleece and coffee, watching my breath curl in the still air while Ragtime rocked gently at her mooring. That’s when I knew we were tipping toward haul-out season, when sails come down, Travelifts creak into action, and summer’s stories get tucked away with the dock lines.

This time of year always makes me think of Billy Joel’s “Famous Last Words,” with its imagery of chairs stacked on tabletops and moorings pulled for the season. For me, his music carries the scent of salt, scraped barnacles and diesel at Smith Cove, on Connecticut’s Niantic River, where Ragtime was hauled. It was never glamorous work, but it was grounding. Our annual ritual marked the turning of one chapter and the anticipation of the next.

Not all sailors know this pause. In the tropics, where I’m based now, seasons blur into one another. In the southern hemisphere, spring is just beginning. But no matter the latitude, there’s an often-understated theme among cruisers: The real magic lies less in the miles traveled than in the moments fully realized.

I was reminded of that recently, recalling one summer when our cruising plans stayed close to home. The gearbox needed work, and the busy summer schedule ashore required shorter hops, so we seized a few opportunities to meander along the southern New England shoreline, never more than 40 miles from our slip. We met people that summer who would become some of our closet cruising buddies. Mike and Donna, owners of a plucky Cal 25, traded stories and swigs of sauvignon blanc like currency. Chuck and Marge, whose custom 29-foot double-ender classic yawl was the curiosity of every anchorage, waded for clams in the muddy shallows and always shared their catch. And as our cruising plans quickly adjoined, these friendships, anchored in the simple joy of being out there, became the real souvenirs of the season. We weren’t chasing trade winds or scratching ports of call off a bucket list. We were simply cruising, and that was more than enough.

Presence doesn’t require a passport or a thousand-mile passage. It’s also in the laughter that carries across an anchorage after dark, the muffled clink of plastic wineglasses in the cockpit, the stillness before dawn when the harbor is nothing but shadows and sound. These are the moments that last, the ones you find yourself replaying when the boat’s on the hard and the white stuff starts to fall.

Haul-out season is when I would always find myself holding on to those moments most tightly. As my family and I prepped Ragtime for another long winter’s rest, we would talk about that squall we so courageously navigated, that bluefish we unexpectedly hooked onto—and somehow landed—while readying for a tack change under full sail, the foggy morning coffees in cozy anchorages that felt like they belonged to us alone. These memories become the “last of the souvenirs” Billy Joel sings about in that song—sweet, enduring and carried forward into the off-season.

And then, of course, there’s the practical side. This is when the hands-on sailor in all of us gets busy—winterizing pumps and plumbing, staying ahead of hull and deck maintenance, giving engines and onboard systems the TLC they need to wake up strong in the spring. In this issue, our Hands-On Sailor section is packed with advice from fellow cruisers who’ve been there, done that and learned a few tricks to make the process smoother. 

These projects may not be glamorous, but they’re as much a part of the cruising life as plotting the next waypoint. Because in the end, the close of the season isn’t an ending at all. It’s simply part of the cadence. Boats come out of the water, tools get stowed, and we look to the next chapter, but the magic remains.

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