Just because I have spent most of my life sailing in warm climates doesn’t preclude me from having huge amounts of fitting out experience. Growing up racing dinghies in Southern California and now sailing toward retirement in Florida only gives me a longer sailing season than much of the country. It doesn’t mean never having to use the words “fitting out.” 

In fact, the words I usually hear immediately before fitting out are “worn out.” Warm weather skippers sail their boats into destruction since they don’t have winters of ice to remind them to store their boats and then fix them up for the sailing season.

I have, in fact, used exactly 84,204 sheets of sandpaper over the past few decades to prep rails for varnish or smooth bottom paint before a roller job. That’s an exact count, by the way, done from the thousands of West Marine bills carefully hoarded by She Who Must Be Obeyed in a file marked “Why Do We Own A Boat?” 

So I’d like to share that vast experience with Caswell’s Top 10 Rules of Fitting Out.

No. 1. A little blood must fall. Bloodletting has been an integral part of every fitting out since the Vikings sacrificed slaves while readying their boats for the summer pillaging season. In fact, that ouch on your finger from a meathook on the wire jib halyard is just Mother Nature’s way of telling you it’s time to replace that halyard. A box of Band-Aids and some Neosporin are just as essential to your fitting out toolbox as a Phillips head screwdriver and a corkscrew. 

No. 2. Laugh. Things are going to go wrong. It’s a boat, after all. 

No. 3. Never let your hands or tools go somewhere your brain didn’t go 30 seconds earlier. Just because a bolt doesn’t want to come loose is no excuse to grab a bigger wrench or, heaven forbid, a hammer. The result will just add items to your “to do” list for fitting out.

No. 4. When planning your projects, use the “inverted pyramid” method with the most important things at the top, tapering off to the piddly stuff. Fitting out your boat has easily understood starting and ending points. You start when you have money and you end when you don’t have money. Use the inverted pyramid, and you’ll bag the important stuff before the checkbook empties.

No. 5. Think it through. I have a friend who decided that one of his projects was to renew the upholstery in the cabin. Then he decided to overhaul the engine. You see where this is going? His doofus mechanic used the new upholstery as a workbench for his tools and perhaps even the old oil filter while working on the engine. 

No. 6. Think it through even more. Over the years, several impetuous friends have grabbed a drill and started drilling without due diligence. One discovered his fuel tank. Another drilled into his icebox. And yet another pea brain severed several important wires that were almost impossible to reach. 

No. 7. Beware the “might as wells.” These pop up when you’re doing one project and you get sucked into doing a second project that magnifies the cost and effort geometrically. One friend decided to replace the headliner in his boat. Then he thought, “Hey, we might as well replace the lights with LEDs at the same time.” Mistake. Big mistake. The headliner would have cost X dollars, but replacing the lights (and the wiring and the switches) was X to the fourth power.  

No. 8. Ask advice. I know, all guys hate to ask for advice. It triggers some DNA deep inside that whispers in our ears, “You’re a wimp. You’re a wuss.” I was considering a project on our ketch and was waffling. With female brilliance, SWMBO said, “Go ask Fred down the dock, who just did it.” It was great advice, because Fred’s answer was, “Don’t.” He had tackled what he thought was a one-day project but which bloomed into a month of weekends, eight trips to West Marine and finally hiring a guy to finish it. You don’t have to take the advice, and just asking sometimes frees your mind to rethink your plan. 

No. 9. Break every project into itty-bitty pieces. Some projects can seem monumental, like refurbishing the tender. But when you take the pieces individually, like varnishing the oars, it becomes manageable. And you can even take parts home and do them in the garage. Rather than planning to varnish all the toerails and handrails, just do one. Better yet, get into the program by just varnishing the tiller. Having that done makes you feel accomplished, and yards of rails will then fall into place. It’s easy to be overwhelmed by a big project, but dividing it up will give you hope that you can someday go sailing again.

No. 10. Laugh. It’s just a boat, after all.