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Photos courtesy of Misty Tosh

You’ve bought a sailboat. It makes your heart flutter and sets you dreaming about escape.

NONE OF THESE THINGS matter if you don’t understand the inner workings of your vessel and exactly what you plan on doing with it.

I’ve gone down that road three times now, going from 25’ to 30’ to 36′. If you’re thinking about making the same decision, learn from the lessons I’ve picked up while on my own personal quest for freedom.

‘On the hard’

Most likely, the boat you buy will be “on the hard”, which is sailing lingo for “perched in a dusty corner of a boatyard”. Your job is to bring it back to life.

The first thing you need to do is give it a good bottom paint job. This goes double if you’ll be sailing in saltwater: there are all manner of sea creatures waiting to cling to the bottom of your new toy and eat away at the fiberglass.

Check all your thru-hulls (various holes in the hull designed to bring in and flush out water) and seacocks (small handles that open and close said holes). Make sure that the fittings are secure: there’s nothing more horrific than a hose popping off and flooding the engine room.

After stepping the mast and giving the engine a tune-up, oil change, and systems flush, you’re pretty much ready to put your boat in a slip and form a plan of attack.

LESSON LEARNED: I stayed in the yard way too long because I was intimidated to put my boat in the big Pacific Ocean. But I also met and bonded with a cast of salty characters who have proven indispensable to my current foray into boating mechanics.

Take inventory of the madness on board

The first step in developing your soon to be encyclopedic knowledge about your boat is to rip it to shreds. And I mean really tear it to pieces.

Don’t just look in the lockers – get in there and pull out everything you see . Cupboards and hatches hold incredible amounts of tools, manuals, old parts, lines, cleaning supplies, and electronic equipment.

You have to research what you have, ditch what you don’t need, and come to know the rest of the gear you’ve been blessed to inherit.

After you’ve pulled out your boat’s innards, organize your items and create a master list with photos. That way, when you are freaking out and needing a zip tie, you’ll know exactly where the rascal is stowed.

LESSON LEARNED: I spent hundreds of dollars and uncountable hours at the store buying stuff already buried somewhere on my boat. If I’d inventoried it to start, I’d have been one step ahead.

Systems Management 101

Everything on your boat connects in some small way, and there is a correct way to assess and interpret this blueprint. It is most definitely not by killing a 6-pack and gazing at the stars from the cockpit.

Trace electric lines and figure out what your battery bank is connected to. Rap on tanks and see what corrosion they might have. Check all your hoses and clamps. Read your manuals. Simply put, fiddle with shit.

Once you become good pals with the wildness that lays just out of sight, things become clear. Suddenly, all that mechanic mumbo-jumbo ain’t so bewildering.

LESSON LEARNED: Getting a proper survey is crucial, not only for insurance purposes, but for learning about your boat.

I was tossed 32 pages of cryptic chaos and hundreds of photos after my master surveyor departed. This incredibly detailed document has been invaluable in learning about my craft as well as figuring out what I need to do to bring it around to its prime.

Plan ahead

Be realistic about your future jaunts. Are you sailing around the world? Are you island-hopping in the Caribbean? Are you day sailing in the Great Lakes?

Each of these adventures requires a different schematic and breakdown. If you are tied to shore power in a nice slip in Chicago, you don’t necessarily need a bunch of solar panels, wind generators, and autopilots.

But if you are going on the escapade of a lifetime and hitting the high seas, you absolutely want all of the above, and then some.

You may think you want to take off into the unknown, but get a little practice on the home turf first. Do a night passage. Hell, spend a few nights on the boat – they definitely aren’t spacious, and sometimes not even comfortable.

Imagine downsizing your life in a severe way. Can you do without the giant flat screen and handy washing machine? Can you handle squalls that make you want to piss your pants? All these things have to be considered. Take it one step at a time so you don’t feel overwhelmed.

LESSON LEARNED: The very first thing I did the moment I bought my boat was purchase a watermaker. I’m currently hooked to shore power and have a nice hose that fills my tanks. When I sail around the world in a few years, my Power Survivor will probably be discontinued. I could have used that 3k for a myriad of other upgrades. Point being, prioritize.

Get to know your local ship store

The chaps at the ship store are a bunch of grizzly think-tanks. They have knowledge about boats that would blow your mind, the sorts of nuggets that only come from years of experience on the water.

They’ll rattle on about hose sizes and sail plans until you’re panicking. Sometimes you’ll leave thinking “will I ever know anything at all?”

Most times, though, you’ll leave thinking, “God, I love free information.” Pick brains, scour bookshelves, park yourself in unfamiliar aisles, and study the backs of random boxes.

This, my friends, is how you learn.

LESSON LEARNED: Don’t be afraid to ask advice. Just take it all with a grain of salt. Everyone claims they have the best diver, the best rigger, and the best mechanic. You just have to meet these people yourself.

Bookmark these useful sites:

Community Connection

If going it alone isn’t your style, take a look at How to Travel the World by Crewing on Yachts on the Traveler’s Notebook.

Beginner's GuidesSailing


About The Author

Misty Tosh

Misty Tosh is a producer and director in the wild world of indie filmmaking and television. Past shows have taken her to Africa, Spain, Mexico and Nicaragua, and when she's not ensconced in production mayhem, she can usually be found in an exotic third world locale tracking down the indigenous liquor. She's in the midst of creating an NGO promoting sustainable community empowerment in distant lands and is currently on a volunteering/research escapade from Mexico to Panama in her 14' solar powered vintage travel trailer.

  • Richard

    awesome piece, reading this entertained my dreams of one day doing just that, buying a small sailboat and drifting off.

    • misty

      It was possibly the wisest thing I have ever done with my money.

  • Eva


  • Travellohr

    I looked at your blog. You really turned that boat into a beauty. And you are brave – around the world?!

  • misty

    I will say this latest Carib jaunt has made me want to sail away to the S. Pacific stat. All in due time, I suppose….

  • Autumn Washington

    wind generators are good alternative for fossil fuel driven power generators”*

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