For the past 6 years i’ve taken myself from someone who, under stress, couldn’t tell port from starboard, to capable of skippering a sailing vessel in just about any spot on this liquid covered ball. Here i share the top ten steps toward you making that move, living your dreams and setting off to sail.

10. Take a class. Heck take a few.

There are two sailing outfits in the U.S. The American Sailing Association (ASA), and U.S. Sailing. Go with US Sailing if you are interested in yacht, dinghy, windsurfing, and radio sailing racing. I chose ASA because they are focused on cruising, the art of living and traveling to various ports.  ASA tends to teach you how to handle yourself in more of a cruising sense, where US tends to focus on the racing side. Starting off in a class means first, you’re going to end up with a coach that has already seen your mistakes. Second, you’re probably going to be driving something like an Ericson 27 which if by chance you happen to bump the dock a little hard, relax…they’re built like tanks.  Third, you have a great deal of confidence when you’re surrounded by other people learning, making mistakes with you, not to mention that good ol’ skipper who may just be the gatekeeper to your dreams.

9. Sail…then sail some more.

You're bound to make friends sailing

My old swim coach used to say “If you want to be a better weight lifter lift more weights! If you want to swim faster swim more!” Which is horribly simplified, but hey the guy had to yell something at us. The same can be said for sailing.  The first time i went out i was nervous. By the time i had taken a few classes, spent a bit of time sailing, i felt the normal confidence that comes with experience.  There’s always more to learn, but there comes a point where the basics make sense, things start to click, and you begin to relax as you realize it’s just not as hard as you think.

8. Start a healthy drinking habit.

Yep. You heard me. Alright, i admit maybe you don’t have to drink but you can cross the world over and there’s one thing all wayfaring sailors seem to have in common. They like to drink. Which translates in to nearly all sailors meeting in a bar or two within stumbling distance of the marina. There’s the place to go to find the most information about weather, crossings, local currents and tides, not to mention repairs and supplies if you decide to sail abroad.

A great read that just about covers it all

7.Read

Books such as Dove by Robin Lee Graham and and Sailing Alone Around the World by Joshua Slocum will cover your inspiration and get you started understanding that your dreams can be accomplished.  There are loads of technical books covering all aspects of sailing, but to get you started I recommend one that covers the bases.  Also you can gather a lot of knowledge from forums like Sailnet.

6. Crew

There are loads of boats out there that are too big for one person to sail.  This means opportunities abound for willing crew to assist skippers in passages and general boat maintenance.  What this means is you may find yourself traveling to places on the cheap that are impossible to access using your land lubber tourist guide. You can learn a lot from an old sailor, even more while you’re sailing.  Not to mention the added bonus of logging sea time, which is an important step in getting future crew jobs and eventually your skipper’s license, should you decide.

5. Join a Club

Let’s be up front, having gained a lot of salt at the Tradewinds Sailing School and Club, i admit my bias.  There really are a lot of benefits to joining this kind of club.  Although not as inexpensive or as thrilling as crewing, clubs don’t require you devote weeks at a time to sail.  Instead, as is the case with Tradewinds, you pay a monthly fee for unlimited sailing on a fleet of boats, or Marina for example has a program where you pay a small fee then pay charter fees per use.  Which type is right?  Depends on how much you sail. Look for one in your area.  Even inland you can usually find folks hunting for wind on local lakes.  Locally old school yacht clubs are in sharp decline, especially the ones that have not adapted to the younger generations.  Talk about a wealth of knowledge!  Not to mention if you join one they have what’s called “reciprocal” relationships with all other yacht clubs.  Which basically means you join one…you join them all.  Around the world you will find a yacht club in nearly every port.  Go have fun.

4. Crash a Beer Can Race

The easiest and fastest way to get yourself on a boat, granted perhaps as rail-meat, is by stumbling on the docks of one of these local yacht club and inquiring about beer can races.  They’re usually held on Wednesdays but call ahead and check.  Inquire as to their membership, tell them your name and ask how to go about sailing a beer can race.  Show up well ahead of the race with non-marking soled shoes, sunglasses, appropriate rain gear (you may get wet), and a 6 pack of good beer and you just may coerce your skipper in to allowing you the honor.  When you arrive ask permission to enter (some clubs require a sponsor), tell them you would like to race and help in any way.  Sit back, relax before-hand, have a beer if that’s your thing (hence the name), and throw it out there that you are looking to crew for today’s race.  Almost inevitably you will find a willing member who will take you on board.

3. Pound the Docks

Dockwalking is the art of finding busy docks, then “walking the dock” offering your service as crew.  This is hit-and-miss as you may guess, but it’s often the method that works.  Depending on the season, you can find a number of different vessels by word of mouth that are in port for repairs or resupply.  The reason being is most sailors who need crew aren’t a part of yacht clubs, crew lists, or message boards.  Stick it out and you may be pleasantly surprised by getting your ropes aboard a real sail boat.

2. Form A Partnership

Finding a fellow sailor isn’t hard.  Finding one that’s as dedicated, reliable and financially sufficient is often the problem.  Still, partnerships work well with people who understand the level of dedication that goes in to maintaining a boat.  Laying out expenses, terms, and multiple “what if” scenarios in a contract is the standard these days.  Attorneys in areas of maritime activity usually have a boiler plate contract or you can simply create your own.  Find several so you get an idea of what to expect.  I have seen people who were sailboat partners and friends even for 20+ years.

1. Buy a Boat.

Buying a boat is usually the most attractive option for a new sailor.  It’s seems much easier to make mistakes on your own, without the embarrassment of classmates and instructors.  After all you can just read the book and you’ll be ok, right?  Wrong.  Truth is the sea claims lives.  It does not care if you’re a good person or if you tried hard.  Buying a boat without learning is bad news.

Yet the process of buying is much easier than you think.  If you’ve ever purchased a home you know how a broker works.  Find a good buyer’s broker before you start to look.  They can save you a lot of time, effort, and heartache through the process by bringing their knowledge to your side of the transaction.   It’s easy to walk in to a trap in boating and a broker can save you from those traps.

Buying the boat, however is only the beginning.   There are more than a few boat owners who were bit by the sailing bug and regretted their purchase. Do your research before jumping in to this one.

This soon-to-be grandiose spot exists as my personal soapbox, epic escapade on ice, quirky muse and gleeful attonement for mine transgressions.  It’s these following gifts of tomfoolery, puns and cheap humor i present in a cheerful attempt to poke a pointy stick at the roadkill of entertainment.  Join me, sprinkle some salt on your cantaloupe, touch your toes ten times, and repeat after me: when we work together we can eat some cereal.