Dry bag, dry gear
I stumbled upon Glacier Clear Dry Bag while browsing the aisles of APS Ltd., in Annapolis one fall, and as a fan of the roll-top drybag, it instantly caught my eye: finally a drybag that allows you to see its contents, rather than blindly digging into the bottomless hole. There’s pros and cons, though: you see what you have inside, but so too, does your weight-conscious skipper who can see how many clean pairs of underwear and magazines you’re smuggling onboard. It’s worth it though, and you can’t beat the waterproofness. If you’re sailing sportboats, you’ll be glad you have it when your bag gets shoved in the wet bilge. The medium-sized bag (recommended for a day race) is $21.95.

Toasty domes
You’d be hard pressed to find a lighter (1 oz.) and more effective temperature regulatory device than the Patagonia Capilene 4 Beanie. Putting it on can take the chill out of a cloudier—or windier than-expected—afternoon; taking it off opens the human body’s primary heat vent (the top of the head). When not covering your dome—hirsute or chrome— it’ll fit into the smallest of pockets. And it does not absorb water. What more could you want for $25?

Speed in hand
One-design dinghy sailors have long been disciples of relative speed. It doesn’t matter how fast you’re going as long as it’s a fraction faster than the boats around you. That’s one of the beauties of one-design racing. There’s also the fact that installing speed-monitoring electronics on a dinghy or a small keelboat has been a serious hassle. But with Velociteck’s Speedpuck, this is no longer the case. The GPS-driven speedo and compass is completely self-contained—it runs on three AA batteries—and mounts just about anywhere with some industrial-strength hook-and-loop fasteners. While racing, it monitors speed to the tenth of a knot, heading, and whether you’re headed or lifed. It also records your track for review later (initially this feature only worked on a PC, but now there’s a program for Macs, provided you’re running OS 10.6). It’s great for racing in small keelboats and dinghies (double check that it’s not against class rules), or for solo training. $336, velocitek.com

Freeze frame
It was always the ultimate conundrum for the sailor/photographer: how to get good onboard images. The best photos always came when the conditions were most likely to ruin expensive camera equipment. Waterproof housings were one option, but they turned even a nimble point-and-shoot into a cumbersome appendage. The Olympus Stylus 8010 is one of a handful of high-megapixel cameras that can be dropped, submerged, and (in the case of the Olympus) frozen. The zoom is limited, and the quality won’t match that of the top digital SLRs, but it will likely outstrip the best digital point-and-shoots you found under the Christmas tree three years ago. It also takes YouTube-quality movies and will fit comfortably in your pocket. MSRP is $400, but it can be had for much less (try amazon.com).

For professional marksmen
Some sailors can sense boatspeed through their butt and evaluate sail shape down to the millimeter with a squinty glance. For the rest of us, it’s about working to find the right settings for each condition and then remembering them. That’s where a multicolored electrical tape pack (and a few permanent markers) will come in handy. Mark sheets, halyards, jib tracks, the outhaul, the cunningham, and the boom vang. When you’re going well, note how the marks line up for future reference. At $2.49 (HomeDepot.com), speed doesn’t come any cheaper.