I don’t know about you, but I’m a little uncomfortable drilling holes in my sailboat. I avoid them if I can. And when I can’t, I want them to be right the first time. Do-overs aren’t pretty. Whenever I have to drill holes to install deck hardware, I’m even more hesitant.

One of the reasons is that if you don’t drill the holes perpendicular to the deck surface, it can cause problems below. Due to the deck thickness, if the hole isn’t perpendicular, the location on the underside can be very different from the topside. You should always use fender washers under the deck, but if the hole spacing is close, there might not be enough space between the holes for the washers to sit neatly side by side. Plus, it just looks sloppy. If the hardware will be in plain sight, you’ll be looking at them for a long time.

One solution is to use a drill guide. There are many different ones available but the Big Gator Tools V-DrillGuide in particularly is handy for getting into places that larger guides won’t, which is often where deck hardware needs to go.

Most of us don’t need the 17 different size holes that the V-DrillGuide fits. You can make a similar tool if you have a drill press and save the $25 for more stainless steel fasteners.

Use a piece of 3/4″ scrap hardwood such as oak and using your drill press, drill one of each size hole that you commonly need similar to the picture below. Mark the size of each one with a fine tip Sharpy marker.

The next time that you need to drill a hole in a deck, use the guide to hold the bit straight while you drill. You can pay more attention to the cutting action and worry less about the angle of the hole. You’ll get more accurate hole spacing on the underside and results that you can be proud of instead of embarrassed.