Choose Your Cruise: Upwind V.S. Downwind Sailing

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Knowing Wind Direction for Sailing

So you’ve just purchased a sailing dinghy, daysailer, or liveaboard, and you’re ready to take it out for a cruise. You're sunscreened up, hooked up the  trolling motor to your inflatable boat, and are trolling away from the dock towards your mooring. No destination in mind; just you, your boat, the wind and the water. You probably know something about the points of sail, and would be able to navigate to a given location with proper steering and sail trim – if you had anywhere to be. But lacking any set destination, it might be a bit less obvious what kind of course to plot for maximum enjoyment and relaxation (or exhilaration!). Taking a look at the differences between sailing upwind and downwind will clarify your options and help you to choose your cruise.

Obviously, geography is a limiting factor here – you wouldn’t sail straight into the rocks downwind just for the sake of going on a run – but we’ll put navigational necessities aside to focus on the experience of open water at your bow, and a skipper’s choice in which way to turn.


Zig-zagging upwind is a maneuver that many beginning sailors at first find rather difficult, but once they master, tend to love – an upwind course is extremely dynamic, and can be very satisfying to navigate successfully. Moving upwind, you’ll be tacking back and forth from close-hauled to close-hauled, sails trimmed in until they’re just about in line with the center of the boat. On a close hauled point of sail, you’ll be moving quickly – the boat will be propelled forward by the lift created by the curve of your sails, and kept from slipping by the pressure of water on the centerboard or keel. And you’ll feel the speed, too. Traveling against the wind direction, air will be rushing toward you and you’ll be rushing toward it, making the fact of your motion extremely perceptible. In other words, the apparent wind that you experience will be more powerful, strengthened by the additional wind created by the forward motion of the vessel. Following an upwind heading is also when you’ll be most likely to experience heel, the phenomenon of your boat tilting to leeward as it travels forward. This is corrected in a dinghy by hiking out over the windward side, or otherwise by easing the main sail until the craft is level.

Choose an upwind course if you’re in the mood to feel the wind in your face and get moving. If you’re looking for a more active cruise, tacking back and forth, trimming and easing the sail(s), and continuously adjusting your steering to remain on a close hauled course will be a great way to keep your hands and body moving and your mind engaged with the voyage.


Sailing downwind is generally an easier and more relaxed option. On a broad reach or run, the sail will be eased out as far or nearly as far as it will go, perpendicular to the wind on a dead run. Rather than pulling the vessel onward, the sail will act more like a parachute in front of a giant fan, pushing you forward in the same direction as the wind. This means the apparent wind will be at your back – you’ll indeed be moving more slowly than you would on an upwind course, and you’ll experience a much more comfortable ride. Traveling in the same direction and at approximately the same speed as the wind, you sometimes won’t feel like there’s any wind at all! The only thing you’ll need to focus on is steering a straight course and avoiding accidental gybes, especially in a dinghy.

Choose a downwind course if your idea of a good time on the water involves a face full of sunshine and a cool beverage in hand. With an eye on the wind direction and a steady hand at the helm, you’ll have plenty of time to relax, take in the scenery, and maybe even engage in some light daydreaming in the lulls.

Conditions and Reaches

Of course, your choices will also depend on the weather – the above is based on an assumption of ideal cruise conditions; sunshine, calm water, and a steady breeze. But your course can easily be adjusted on the fly. On a particularly hot day with a light breeze, trim in your sail and head up from a run to pick up speed and let the wind cool you down. On a gusty day with choppy waters, maybe a downwind heading will provide all the sport a thrill seeker needs. And then there are the reaches to consider; close, beam, and broad. On a close reach or broad reach your experience will be similar to those provided by sailing upwind or downwind, respectively. A beam reach in dead center provides a bit of both worlds, a speedy ride and an easy cruise at once.

And when it comes to a pleasure cruise, no direction is really a bad choice. Hoist the sails and enjoy the ride!

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