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Windshifts: When to Go

For dreamers of all ages, the idea of cruising has an inescapable allure. But the question always remains: “When should I go? When can I realistically trade my current life for the freedom of cruising?”

For dreamers of all ages, the idea of cruising has an inescapable allure. But the question always remains: “When should I go? When can I realistically trade my current life for the freedom of cruising?” Whether you are young or have been young for a long time, whether you hope to cruise a coast or circle the globe, the answer is simple, but elusive. It evaded me for half a lifetime. 

Barely out of my teenage years, I heard about a magical path known as the Intracoastal Waterway, a series of canals, rivers and sounds that can take one south, far away from winter. The dream of sailing the ICW lodged itself in my brain. The question was never “Will I go?” but “When?” But with a lifetime ahead of me, loans to pay off, courses to complete and summer jobs to find, I knew the time was not now. 

Years later, as a young married couple, my wife and I sometimes gazed together at the sailboat classified ads. The perfect boat was always there, but seemed financially out of reach. We were new to our careers and lived in a tiny apartment. We needed to save for a house and focus on our jobs. Now was definitely not the time to go sailing.

Small babies arrived, and they soon became toddlers who tripped and tumbled with ease. We obviously could not become a cruising family with clumsy toddlers aboard. We were overwhelmed young parents, and dropped into bed each night exhausted. We no longer had time to look through sailboat ads. We juggled children, mortgage payments and jobs that took us farther from our family than we wished. Clearly, for us, the time to go was not now.

We decided we would delay the freedom of cruising until we had climbed our respective corporate ladders, completed our careers, and retired. That way we could be sure our children were firmly established in their own lives before we departed. We would downsize our house to the perfect boat that we would be able to comfortably afford.

Before we knew it, though, our children were halfway to adulthood and we sensed their childhoods were passing us by. Our kids were energetic and adventurous, ready for anything. We felt that maybe, just maybe, now was the time to go.

Stepping out of real life for a year or three to cruise is not easy, and there was much to be done. There were forms to fill out for sabbaticals and self-funded leaves from careers. When we told employers we would be taking a year to cruise to the Bahamas we received looks of thinly veiled personal envy. 

We purchased our dream sailboat and put our house up for sale. We spent a summer on a shakedown cruise. Our children did not suffer from seasickness and loved sailing the Great Lakes. Maybe we really could go now. The dream had been reawakened.

We purchased charts, rewired and replumbed systems, bought and stowed provisions, and when the first hint of autumn was in the air, we pointed our bow south and departed for that once-mythical ICW. We spent hours together as a family and got to know each other again as husband and wife. We “boat-schooled” our kids and rediscovered them as people. We weathered water pump failures and dragging anchors. We found faint humor in electronic meltdowns and clung to each other in howling winds. Accidental groundings were no longer disastrous, but an excuse to stop for lunch. We sailed past our first palm tree and spotted our first dolphin. As time slid by, we became a cruising family.

Now, as our children play with others their age in George Town, Bahamas, my wife and I sit on the beach, enjoying the brief time we have with them. Peering down the beach, we can see young single cruisers standing in turquoise waters, chatting, laughing and forging friendships that will last lifetimes. Nearby, a young relaxed cruising couple plays with a pair of toddlers who trip and tumble and splash gleefully around the beach. Behind us, under the shade of coconut palms, retired cruisers hold hands and enjoy the winter warmth. Now, if anyone asks “When should we go?” we know the answer. The time to go is now. 

Illustration by Pierre Hervé

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