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?”
Author:
Publish date:
Updated on
Wind_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?” 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

Related

TOTW_PromoSite

SAIL's Tip of the Week

Presented by Vetus-Maxwell. Got a tip? Send it to sailmail@sailmagazine.com No chafe, safe stay  If you’re leaving the boat unattended for a longish period, there’s a lot to be said for cow-hitching the shorelines, as this sailor did. They’ll never let go, and so long as the ...read more

belize600x

Charter Special: Belize

It would be hard to imagine a more secure spot than the Sunsail base on the outskirts of the beachside community of Placencia, Belize. The entire marina is protected by a robust seawall with a channel scarcely a few boatlengths across. It’s also located far enough up Placencia ...read more

DSC00247

DIY: a Top-to-Bottom Refit

I found my sailing “dream boat” in the spring of 1979 while racing on Lake St. Clair in Michigan. Everyone had heard about the hot new boat in town, and we were anxiously awaiting the appearance of this new Pearson 40. She made it to the starting line just before the race ...read more

01-oysteryachts-regattas-loropiana2016_063

Light-air Sails and How to Handle Them

In the second of a two-part series on light-air sails, Rupert Holmes looks at how today’s furling gear has revolutionized sail handling off the wind. Read part 1 here. It’s easy to look at long-distance racing yachts of 60ft and above with multiple downwind sails set on roller ...read more

HanseCharles

Video Tour: Hanse 348

“It’s a smaller-size Hanse cruiser, but with some big-boat features,” says SAIL’s Cruising Editor, Charles J. Doane. At last fall’s Annapolis Boat Show, Doane had a chance to take a close look at the new Hanse 348. Some of the boat’s highlights include under-deck galleries for ...read more

amalfitown

Charter Destination: Amalfi Coast

Prego! Weeks after returning from our Italian flotilla trip last summer, I was still feeling the relaxed atmosphere of the Amalfi Coast. It’s a Mediterranean paradise, with crystal-clear waters, charming hillside towns and cliffside villages, plenty of delicious food and wine, ...read more

image005

Inside or Outside When Sailing the ICW

Last April, my wife, Marjorie, and I decided to take our Tartan 4100, Meri, north to Maryland from her winter home in Hobe Sound, Florida. This, in turn, meant deciding whether to stay in the “Ditch” for the duration or go offshore part of the way. Although we had both been ...read more

MK1_30542

SailGP: There’s a New Sailing Series in Town

San Francisco was the venue of the biggest come-from-behind victory in the history of the America’s Cup when Oracle Team USA beat Emirates Team New Zealand in 2013, so it seems only fitting that the first American round of Larry Ellison’s new SailGP pro sailing series will be ...read more