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Six Keys to Unlocking the Joy of Daysailing

One of the best things about daysailing is being able to leave your shoreside cares behind

One of the best things about daysailing is being able to leave your shoreside cares behind

Let’s be honest. Daysailing, not cruising the Caribbean or racing solo round-the-world, is what most of us sailors do. Be it on diminutive Stockton Lake in southwest Missouri, on Chesapeake Bay with its 11,000 miles of shoreline or on the chilly waters of Puget Sound, most of us do our sailing one day at a time. While we love reading about the adventures of the “sail off into the sunset” crowd, the reality is that most of us will never see that proverbial sunset more than a few miles from our home port.

But before we start feeling sorry for ourselves, let’s count our nautical blessings and see what we can do to enhance them. Aside from the inherent fun of our sport, daysailing, unlike its more exotic siblings, offers us a unique escape from the pressures of everyday life in the “real” world. When that morning staff meeting goes awry or the backup on the beltway is a little more maddening than usual, many of us can be out on the water within an hour. No weeks of planning or preparation necessary: just the desire for the wind and the waves to work their magic in time for dinner.

When old friends drop by for a weekend visit, a Saturday sail offers us the opportunity to catch up on each other’s lives while enjoying the views from our floating patio, all the while leaving Sunday for more shorebound activities. And, of course, on those welcome occasions when there’s nobody to entertain, that Sunday sail is a fitting reward for a Saturday spent mowing and weeding and trimming.

As a daysailor for over 35 years, I’ve learned a few secrets along the way that make my day afloat a little more enjoyable. Some of these may work for you, too.

1. Forget about a destination—just sail!

Somewhere ingrained in the American psyche is the belief that for an activity to be worthwhile it needs to have a goal, a target or a destination. But why? To me, the beauty of daysailing is that I’m unconstrained. I can sail wherever the wind and water allow me, with no need to force a tack or pinch to hold one. And if we want to stop for lunch or a swim, we drop the hook wherever we find ourselves. That freedom and lack of structure is our “destination.”

2. Cap the knotmeter: who cares?

After years of watching our speed and tweaking to maximize it, I discovered that sailing became a lot more fun after our knotmeter went on the fritz a few years back. Those mini-adjustments that kept me hopping all those years didn’t seem so important anymore. And my irritation with the fluky Chesapeake Bay winds, when our speed would drop below 3 knots, all but disappeared. I didn’t know, so I didn’t care.

3. Don’t plan anything else for the day, except a late dinner!

When Peg, my first mate, and I decide to go for a daysail, we make sure our schedule is open for the rest of the day. And if it’s not, we open it. There are few things more exasperating for a daysailor than to chase the wind all day and then have it strengthen just as you’re dropping your sails to head in for a Lion’s Club meeting that evening (no offense to the Lions, but…). On the Chesapeake, the wind seems to know when it’s been outranked and it doesn’t like it much.

4. Leave the boss and the phobics behind

With the limited amount of move-around space on a sailboat, you can’t just hide or take a walk to get away from your guests. Therefore, it’s paramount that you know who you’re inviting aboard and what their “idiosyncrasies” are. If you want to avoid a blood-curdling scream mid-sail, make sure that your guests understand two facts. 1) sailboats heel (sometimes dramatically) and 2) spiders like to stow away in the rigging and can make surprise entrances. As for your boss, if you don’t want to spend the entire day trying to impress, leave him or her on the dock with the arachnophobes.

5. Insist that all electronic devices are turned off

Like the saloon-keeper did back in the old west, make your guests “leave ‘em at the door!” Like the blood-curdling screams of arachnophobes, a ringtone aboard makes my skin crawl. A sailing friend told me recently that he asks his guests to put their phones in the chart table until they’re back on dry land. “Some don’t... most do,” he said. If a guest can’t be incommunicado for a few hours in a day, then maybe an invitation to go sailing isn’t one he should accept.

6) Realize how lucky you are to be a daysailor. The grass isn’t always greener.

For me, one of the true joys of daysailing is the solitude it provides. Within an hour, a daysailor in Boston or Chicago or San Diego or San Francisco or Miami or wherever can go from the controlled chaos of urban life to the peacefulness that communing with nature brings. We’re very lucky to be daysailors, you know. We have the best of both worlds. 

January 2019

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