The Gill Race Cap is lightweight and breathable.

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If there’s one thing I’ve learned over a lifetime of racing on different boats, it’s that we sailors are a needy bunch. Even if our boats are old, we eventually need new sails, we need good wet gear to keep us warm and dry, we need shoes that don’t slip on worn non-skid. We need butt pads, kneepads, and now spleen pads for long days spent creased over the lifelines. There’s all of this on top of the basic essentials: shades, hats, gloves, watches, and more. It’s a wonder we can actually leave the dock without all of it. No matter. Whatever it takes for us to race at full intensity and with full enjoyment is essential equipment. In the spirit of a holiday shopping theme, we are sharing our favorites, accessories guaranteed to make any racing sailor—big boat or small—smile, without dipping into the new-sail fund.

Put a lid on it
The ubiquitous Mount Gay hats are the universal beacon of the vast majority of yachties, but true red-hat zealots would never chance losing their precious cap to a gust and watching it drift away in the wake mid-race. Nope. Leave it ashore and go for something technical, something with a retainer cord and clip. One of our favorites of late is the Gill Race Cap (above, right), a huge seller at the merchandise table at our Sperry Top-Sider NOOD Regattas. It’s an incredibly lightweight hat, really breathable, and there’s a mesh headband to absorb the beads when it’s sweltering. There’s no logo on the front, which makes it a great team hat as well. $19.95

Dry digits
If you’re like me, you have your wife or significant other buy your socks for you. But the one pair of socks you can buy for yourself are of the waterproof variety. I’m talking Rocky Socks, the standard in dry digits. I’ve tried many other types, and none come even close to out-waterproofing and outlasting these Gore-Tex socks. They’re just as good for inshore racing as they are for offshore racing: when you kick off your boots coming off watch, you can walk around a wet cabin. If you can’t afford a pair of sea boots, they’re the next best thing, and take up a lot less room in your bag. Pair Rocky Socks with good, technical wicking socks (ask Mom to splurge) and your feet will never be happier. $59.99

Time on distance
It’s true that a great watch for racing is the one you’ve got on your wrist, and, honestly, for the racing sailor on your list, there could be pages upon pages of excellent options. But you can’t always rely on your run-of-the-mill timepiece to do precisely what you want, when you want it to. I learned this when I started wearing a borrowed Suunto Elementum Ventus. Where most watches take at least two steps to get you into and starting the countdown timer, this one has one-step access. There’s a user’s manual, but you won’t even need it—everything about the functions is intuitive. And I’ll be honest, not a day passes when someone doesn’t say, “Nice watch! What kind is it?” This timepiece will set you back a grand, but if time is money, and money is no issue, it’s worth it. $999

Let there be light
If there’s one inexpensive piece of gear every sailor should have, it’s a headlamp. Racing the overnighter? You gotta have one. Trailering to your next regatta? Get one. It will come in handy when you’re changing your trailer tire roadside, or digging through your trailer box after the party looking for your room key. But no ordinary headlamp will do. A red light is a must to avoid blinding your watchmates. While there are numerous manufacturers and types, a popular seller at sailing chandleries is the Petzl TIKKA XP2, which is lightweight enough to let you forget you are wearing it, and has three white LED lighting modes (maximum, economic, and flashing). For safety’s sake, there’s even a whistle built into the headband should you become hopelessly lost in the mooring field as you attempt to find your boat well past last call. $54.95 (available on amazon.com)