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Learn to Sail

By Linda Janes January 16, 2019

Neither of us know how it happened, but we woke up one morning wanting to live on a sailboat.  It came out of nowhere, nothing but a great dream. We couldn’t sail, and we knew nothing about the water.  But, like in all things, we decided to dive in head first.

We expected this adventure to resemble a commercial for French vodka - our most expensive hobby in history.  Instead, what we found was an amazing community of wholesome people engaged in an activity that spoke to our very souls.  Sailing isn’t hard to get into, if you do it right.

Here’s how:

#1. Find a sailing club (nearby) with a community of people you can connect with, and learn from them.

In our estimation (and we highly recommend this train of thought), it was a good idea to learn to sail before buying a boat.  In the north, there are limited options for sailing schools, but we were lucky to fall into the great company of the Alaska Sailing Club.

Learning to sail at the Alaska sailing club on a Catalina 22 sailboat. Damn Skippy Wear

Image: Alaska Sailing Club Marina, Big Lake, Alaska


This club is a lake yacht club, located about 1.5 hours from Anchorage on Big Lake. It’s a perfect getaway that’s not too far from the city, but still allows us to go sailing even on weekdays, if we can make a hasty getaway from work. Our first impression was that it was a great setting for the whole family and we were going to enjoy it there. 

#2 Consider taking a non ASA certified sailing intro class.

To save a bit on money, this club had a perfect introductory offering - we pay to become members and get a 2 day sailing course as part of the deal at no additional charge. Sure the course wasn’t a certified ASA (American Sailing Association) one, but this is a good way to tell if sailing is something you want to spend additional money on. Likewise, if you’re in a state that doesn’t offer lots of sailing courses, this choice gets you sailing sooner and you can really start to develop your passion for it.

The “textbook” they recommended was Learning to Sail: The Annapolis Sailing School Guide for All Ages, which was excellent.  At this time, we had no idea what the Annapolis Sailing School was, or why it was so special.  The book was amazing though - in 95 no-frills, fun, illustrated pages, it walked us through how to get started and got us ready for our first class.

Learning to Sail: The Annapolis Sailing School Guide for All Ages

For our first class, we stumbled 30 minutes late into a tiny, off-grid lakeside shack in a rainstorm.  The teachers were on a chalkboard, talking about the difference between a tiller and a steering wheel in between sips of coffee.

This was the opposite of all the yacht clubs on TV!  It was a bunch of real people with modest boats, who got together on weekends to play the guitar around the campfire and go race their sailboats.  For a small membership fee, we got a free weekend of lessons on Big Lake, Alaska, and made great friends in the process.

#3 Evaluate. Do you still enjoy sailing?

For us, we were pretty much hooked from the beginning.  Something in the sound of the water, the constant renegotiation of the sail trim, and the tactile connection that our rigging provided between us and the wind… it was magical.

Learning to sail at the Alaska sailing club on a Catalina 22 sailboat. Damn Skippy Wear

Image: Learning to sail on Big Lake, Alaska on an Ensign 22.


We wanted to take the next step, so we signed up to get certified with the American Sailing Association.

#4 - Get the ASA 101 certification (or international equivalent).  It’s your first step towards being allowed to charter a boat, and the most recognizable credential for Americans. 

Our first certification course took us to Kemah, Texas.  Here we did a weekend in the classroom and sailed on Clear Lake, with the outstanding instructors at Bay Area Sailing School.  They were knowledgeable, accessible, and fun. We could not possibly recommend this place highly enough.

Our Alaska instructors had always mentioned that we should strive to find an ASA course that has boats with a tiller and not a wheel. They were fanatical about learning on something that really lets you feel the boat and the water. The bay area school has 22 foot sloops that are tiller operated. And we have to agree, using the tiller is a great way to understand how the motion of the rudder actually propels your boat.

Bay Area Sailing School, Kemah, TX
Image: Bay Area Sailing School, Kemah, TX


If Houston isn’t within your striking distance, you can also find an ASA school in almost any state:

Now all of the little things were starting to fall in place.  We were conversant in the rules, the right of way, and weather.  We could competently dock a boat, rig the sails, and reef. We could tie a bowline knot with our eyes closed (just one eye really).  When we flew back to Alaska, we felt like we were ready for anything.

The great thing about the ASA program is that they really teach all of the hands-on skills you need, from the ground up.  You don’t need to worry if you don’t know any knots or if you don’t know what a sheet is. They’re very meticulous and will bring you from literally zero knowledge to a full working competency in all of the basic skills you need.

Once we had the basics down, we found the best way to build our skills further was to practice - practice racing in particular.

#5 - Nothing will hone your skills as well as racing, so race every chance you can.  Even if it means crewing on other people’s boats...

Don’t get us wrong - in our first summer, we drank a lot of Moscato on sailboats, looking at mountains in the sunshine.  We took lots of photos! And we considered that time very well spent! But nothing honed our sailing skills as efficiently as the days we raced.

When you are racing, you are focused on the little things.  How high can you point the boat without your jib getting angry?  How far past the mark do you need to go before you tack? Did the wind just change a bit?  Who has a free hand and can grab me another beer? You are also using all of the functions of your boat in performance mode (not just for your convenience and fun), so you really get to know the equipment.

We got a lot of repetitions that summer, because we lived close enough to the club that we could go sailing after work, and easily on weekends.  And, of course, it helped that we bought our first sailboat - the lovely Storm Petrel. Stay tuned for our next post on how to buy your first boat!

Learning to sail at the Alaska sailing club on a Catalina 22 sailboat. Damn Skippy Wear

Image: Alaska Sailing Club Governors Cup Race 2017, Big Lake, AK


#6 - Dress the part and carry the right provisions.

Let’s face it, things are better when you live and breathe them.  You aren’t some average joe learning to sail! You’re a sailor. At DSW, so are we and we live that message through our clothing.  Stop by our store and pick up some of your own!

At Damn Skippy Wear, here are a few things we use on our boat. These are gonna come handing. Trust us!

This waterproof solar-powered battery charger is a must.

We also recommend having a set of dry-bags, which you can never have enough of when the rain comes out of nowhere. 

To save you from a huge headache of dropping your phone or wallet in the water, we use this waterproof sports pouch Super handy! 

Learning to sail at the Alaska sailing club on a Catalina 22 sailboat. Damn Skippy Wear

Image: Linda going aboard the Storm Petrel for her maiden voyage with us

Now, you see, there aint nothing to it. Go forth and carp this diem.

Damn Skippy!

From all the @Coastal_Salties at DSW

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About us

Linda Janes - Co-founder of Damn Skippy Wear - Your Seaside and Beach Outlet

 Imagine your perfect day...

Cold dock under your feet, as you watch the sunrise and listen to the waves lapping.

Comfy t-shirts and well fitting flip flops. The crackle of fresh whitefish on a beachside fire, over the cooing of a friend's ukulele. 15-knot winds at beam reach. Tanned skin, with legs dangling overboard. Laughing.

Hammocks... lots of hammocks. Piles of clothes left behind while you skinny dip.

Whatever is in your perfect seagoing/beach day, we want you to have the perfect outfit and all the right tools to make it a smashing success and to remember it for many years to come with the best in coastal home decor and ocean-inspired wear, accessories and novelties.  

In other words, the finest provisions for your seaside adventures!
"Hey everyone! My name is Linda and I get the pleasure of being the chief ambassador here at DSW. 
If you love the ocean, its vastness, and all its shores and beaches, then we're confident that you'll be a lifetime customer.
Welcome to the family!!!"

🌊 🌊 🌊


We are veteran owned and woman-led, and we are from Anchorage, Alaska!

We have so much coastline... so much ocean.  We encourage you to visit Alaska. It is both vast and understated. While here, you can get yourself into any imaginable sport, activity or a way of life. Who knows, your next epic adventure could be waiting for you here, unbeknownst...

"Our purpose is to help you discover and responsibly enjoy your passion for the world's oceans, coastlines and beaches!"

We humbly appreciate your business, if you've purchased something with us. A portion of proceeds from every sale goes to the Ocean Conservancy to help us keep our oceans clean. 

If you're browsing around, check out our Adventure Journal to get you in the seaworthy mood! 

A coastal salty salute to you from all of us at DSW!

Now let's get this show underway...

Damn Skippy Wear. The finest provisions for your seaside adventure.


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