Written by April Winship
October 2021

A double whammy. That’s how I’d describe taking on the cruising life a second time around. As if moving from a sailboat to a powerboat, from two hulls to one, and swapping coasts wasn’t change enough, we are also downshifting into retirement mode.

retirement - cruising life - live-aboard - marinalife
Retirement! On the road to Florida | April Winship

Even after a decade of cruising with our two young daughters, I am not prepared for the seesaw of emotions I’m about to face on our new endeavor. Unlike our previous sailing adventures, this time around won’t be a family affair on the boat, and it’s difficult to wave goodbye as our grown daughters disappear in my rearview mirror.

Ahead of us lays 3,300 miles of highway unfolding like an undulating ribbon. Our destination is the Sunshine State where our new trawler and a new lifestyle awaits. I am acutely aware that we are venturing into uncharted territory, and the thought releases a flutter of butterflies deep in the pit of my stomach.

Life’s transitions, even happy ones, can be unsettling.

I’m surprised that pulling back on the 9 to 5 throttle, slipping into flip-flops and unplugging from the rat race hasn’t happened with a snap of the fingers. But my blinkers are on, and I’m definitely starting to merge into the slow lane.

Beside getting to know the mechanical and electrical inner workings of our new trawler, I am also getting a refresher course in Live-Aboard Life 101. Unless your boat is the HMS Queen Mary, chances are that downsizing is going to become a reality. Shedding possessions is both liberating and painful, and even though I’ve streamlined to the max, every nook and cranny of our 34-foot boat is stuffed.

Frustrated, I let loose a low growl as I dig out a dozen items from the settee locker before finally spying my buried prize. Thrusting my arm up victoriously, I look around for my husband Bruce, but he’s splayed out on the bare fiberglass floor in the aft head (well technically he’s splayed half in and half out over the painful raised threshold) replacing a worn-out head rubber seal.

hauling out - transitions - cruising life - live-aboard - marinalife
Hauling out and sealing the deal | April Winship

Looking like a circus contortionist, he lays on his back and blindly reaches an arm around the toilet bowl in an awkward embrace to slip on a washer and then thread the nut… all by braille. My mind races back to our years cruising in Mexico when Bruce had to reach into the smelly holding tank to fish out a precious tiny pink Barbie-doll high heel that had somehow fallen into the toilet.

“At least you aren’t going to have to retrieve a lost shoe from the holding tank on this voyage,” I say with a chuckle. “Only time will tell,” is his murmured response, which is my cue to pick up a crescent wrench from the neat row of tools he’s lined up, saddle up on his back and start tightening the bolt.

I remind myself that everyday tasks take a bit longer to complete in a boat’s compact environment, and any kind of maintenance on the “to-do” list is often intensified with the tropical heat and humidity. Tempers are ripe for flaring, and we try to remember that the sweaty work is best done away from the midday sun and served with a liberal dose of humor.

While we opted for more comforts in our new powerboat than we had on our spartan sailing catamaran, these added luxuries translate to an additional layer of systems to learn, maintain and repair. Simply put, there is more stuff to break. But we relish a certain amount of self- sufficiency when cruising far from the dock, so mastering the systems we can use has become a vital mission.

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Courtesy of Andrea Fidone on Canva

During the past few months, we’ve been climbing a pretty steep learning curve. I’ve found that previous cruising experience doesn’t always exempt us from our share of heart stopping moments such as trying to dock gracefully in a 15-knot crosswind or even the more mundane relearns such as “Which way does the rabbit run on that bowline knot again?”

Life on a moving platform presents its own set of uncertainties: I wonder if I will get seasick on a monohull? Will I fit in with this new lifestyle? When will I stop jamming my toe into that stupid aft cleat? And the most asked question, when will I finally feel competent?

From my previous cruising experiences, I know there are no shortcuts from novice to expert and becoming a well-oiled team takes patience, practice and time. Even when “newbie” isn’t plastered across my forehead, I know there is always more to learn … another skill to hone.

As we learn to operate and maintain our new boat and settle into the cruising life, the second most asked question on everybody’s mind is “What’s it like being together 24/7 on such a small space…don’t you drive each other crazy?” As with any situation, perspective is everything. I usually answer, “My boat may be small … but look at the size of my back yard.”

For us, cruising is also a shared dream and endeavor, and even with some the bumps along the way the lifestyle resonates with both of us. The rewards far outweigh the risks and challenges of a nomadic life.

In my land life I flat out flunked the art of organization, but life afloat dictates a higher grade. It is all slowly coming back to me, the juggling act of meal preparation and execution with miniscule counter space and pared-down appliances. I’ve come to pride myself in optimizing every inch of our miniature “Suzy Homemaker” refrigerator and freezer.

It’s a balancing act, but as we settle into our cockpit chairs on the foredeck, plates firmly in our laps, the feat is worth it as we dine al fresco, witnesses to a last smooch by the sun as it kisses the horizon goodnight, and we bask in the afterglow of passionate colors.

Set Sail and Live Your Dreams (Seaworthy Publications, 2019) is the Winship’s book about their family’s 10-year adventure cruising aboard their 33-foot catamaran Chewbacca. It is available in both paperback and e-book editions at Amazon.