Fits like a glove
The ultimate cheapskate’s sailing glove was exposed long ago when a dinghy sailor somewhere walked into his neighborhood hardware store, looked at the Atlas Therma Grip display, and thought, “If I cut the fingertips off, these would make awesome sailing gloves.” And so it began. While sailing-specific leather gloves will far outlast the disposable offerings from Atlas, it’s hard not to resist the $3 price tag. And, they’re cool among the dinghy and cat-sailing set. Atlas’ newer model, the Atlas 370 Nitrile Tough, has a thinner coating (said to be three times more puncture resistant than rubber) that has super grip on wet items. That alone makes the decision to go cheap even easier. You can buy a 12-pack for $34 anywhere online (try amazon.com) and be set for a year.

Note this
All the coolest tacticians on the pro-sailing circuit have a Ritchie WetNotes pad either tucked in their backpack or stuck in their back pocket. If you don’t have one, you should get one today. It’s the industry standard for jotting down rig-tune notes, to-do lists, polars, and fast settings. SW’s senior editor, Stuart Streuli, ever the frugal Yankee, cuts his in half; giving him two pint-sized notepads. A perfect $15 stocking stuffer (available on amazon.com).

Cool is fast
A buddy of mine turned me on to the wonders of Gold Bond Powder. Sure, go ahead and snicker, but when I pack for a distance race, it’s the first thing in my bag (I do prefer the travel size for shorter races). Its “triple-medicated” drying powers will do wonders to the clammy environment inside your salopettes. For the extended race, the Extra Strength powder (in the green container) has an extra “medicated” cooling kick. By the time you reach Mackinac, you’ll roll into the Pink Pony fresh as the day you left the Chicago YC’s men’s room. $8

Slices, dices, and opens
Multitools are like the aforementioned watches; everyone has their preferences, especially when it comes to blade size and the number of tools. When it comes to multitools, I’m a minimalist; I only want the essentials; everything else comes out of the toolbox. The best multipurpose knife I’ve used in the past few years is the Leatherman Skeletool CX. You’ve got your 2.6-inch stainless steel blade, pliers, bit driver, pocket clip, and carabineer/bottle opener, which, by the way, does not require peeling back eight other tools to access. It’s 4-inches long (closed), weighs only 5 ounces, and has the carbon fiber, so you’ll ooze fast when you whip out the opener to crack that post-race Heineken. $72