While many sailors heading to Key West for Race Week are (or at least consider themselves to be) grizzled veterans of the venue, more than a few aren’t. We’ve put together a quick and dirty checklist of must-have gear for the southernmost regatta in the United States.Let’s start from the ground up with footwear. For the boat, you’ll need a good pair of deck shoes. Our favorites include Sperry’s new Figawi 2, www.sperrytopsider.com, which is available in five styles. Thanks to Sperry’s Active Drainage System (holes in the sides and soles, basically), and materials designed for low water absorption, they’ll dry quickly. Figawis don’t mark or scuff decks, and their Hydro-Grip soles will help keep you on the boat. A hint for those who hate wet shoes in the morning: stuff your wet sneaks with crumpled-up newspaper every night and they’ll be dry as a bone in the morning. Key West’s streets can be grimy, so wear your flip-flops for the walk to the boat, leave them on the dock, and don your boat shoes once aboard.Sure, it’s warm in Key West most of the time, but veterans will remember the final day of Race Week three years ago when the temperatures dropped below 40 degrees and half the fleet chose to end the regatta Thursday night. What we’re getting at is this: bring gear you might not think of bringing to tropical climes, such as a warm hat. Check out Patagonia’s Beanie Hats, which are light, compressible (i.e., fit under foul-weather gear hoods), and wick moisture away from your noggin. www.patagonia.com Your hands have softened since the summer racing season, so sailing gloves are probably a good idea. We especially like Gill’s Pro Gloves. They last a long time, have sticky grip palms, and have been designed with a contour fit. www.gillmarine.com Cotton t-shirts are great for hanging out at the tent, but lousy on the water. Bring along a week’s supply of wicking base-layer shirts. A lot of manufacturers are offering them these days, and some are great. We like the versions made by Under Armour, www.underarmour.com, Patagonia’s Capilene Silkweight, and Dryshirt’s SPF-50+, www.dryuv.com. Get the long-sleeve version, which allows you the option of protecting your arms from sunburn.At the tent every night you’ll see those who wore sun protection, and those who didn’t. Those who didn’t look like french-fried raccoons, and are most likely suffering. Use plenty of sunscreen and consider wearing a floppy hat with a 360-degree brim. Try out your sunscreen before you head to Key West, as some brands, when mixed with salt water and sweat, can sting your eyes. Take some to the gym and slap it on before your workout to make sure it’s OK. We’ve taken the marketing bait on some sunscreens made for kids, thinking that, like baby shampoo, if it’s for kids it won’t sting your eyes. We were wrong. Sunglasses are essential for Race Week, and we’ve spent plenty of time talking about them online and in the magazine. Suffice it to say that cheap sunglasses are great for the budget, but hard on your eyes. Take a look at shades specifically designed for on-the-water use by Costa del Mar, www.costadelmar.com, Kaenon, www.kaenon.com, and Maui Jim, www.mauijim.com. Our final tip for racers heading south has to do with Key West’s hedonistic pleasures. As you lurch out of the hospitality tent every evening, trying to decide whether to head for your bed or make a night of it, remember this: This time of year, the sun rises in Key West a little after 7 a.m., your harbor start is at 8, and the first gun sounds at 10. ‘Nuff said.