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Feature photo by ccgd. Photo above by ronnie44052

Always dreamed about having your own sailboat and taking the ultimate trip? If you’ve dismissed the idea as too dangerous, too expensive, too difficult, take another look.

SAILBOATS CONJURE UP the most romantic visions. Seeing their silhouettes at dusk makes it easy to think of chucking it all and heading off into the wild reaches of foreign seas. There will be extreme adventures, new discoveries and no one to answer to ever again.

The reality, though, is that a sailboat is a few tons worth of fiberglass and steel and you must have some skills to operate it. Thousands of questions have to be answered before you set out, but the bottom line with boating is—just make the decision.

Here are the top five pointers about boating that I’ve picked up from my own never-ending quest for the perfect lifestyle.

1. Knowing how to sail is not mandatory

My unforeseen dive into the boating world began when I stumbled upon a colorful painted picture on a piece of notebook paper. The picture, posted on a phone pole in Santa Monica, was of a small sailboat, much like a child would create in grade school. It was just the hull, painted bright red, and a simple dark blue sail. Underneath were the words “FOR SALE.”

A long lost fire was reignited with that one chance encounter and before I knew it, I’d bought a 25’ sailboat on eBay (2k) and was driving into the remotest corners of Baja, Mexico to learn how to sail it—just me, a tiny boat and a salty captain.

Photo by gupana

Essentially, I put the cart before the horse and let my overwhelming thirst for adventure get the best of me. Boat first. Lessons later. Who cares? I simply did some online research and found a five-day course that offered a US Sailing Certified program, one where the entire week was spent on the water, not in some stuffy classroom looking at pictures of tying knots.

I figured by the end of the week I’d be able to sail, with a crew, quite efficiently. Instead, by the end of Day 1, I was already single-handing the thing–tacking, jibing, running the sails, steering in and out of the harbor, and living and breathing the points of sail to the tune of sheer exhaustion.

I went into the bowels of Baja a complete novice and came back tearing up Highway 1 certain that when the time was right: here I come tropical waters.

2. Eventually, the bells and whistles do matter.

When you are looking at your first boat, it’s common to get wrapped into “What sort of vessel can I procure for nothing?” That was my MO for my first boat (which I sold due to relocation), but for my second boat, I wanted upgrades. So, after I came into a small windfall of money from a TV show I’d just worked on, I bought a 30 ft. C & C on a whim and outta nowhere, I was back in business.

The basics were already in place: refrigeration, USB radio, roller furling sail, single-handing setup, but for me, it became about vanity and comfort. I spent the summer working on the boat, installing a top-notch stereo system with kickin’ cockpit speakers and main cabin built-ins; replacing crummy dock lines and cleaning up my slimy fenders.

I had a pal recover all the interior cushions and make tropical themed curtains; I ordered new cockpit cushions; and I set up a top-of-the-line GPS system with full high-res satellite imagery, a handy fishfinder and my favorite, a g2 Vision card (imagine aerial color photos of unfamiliar marinas and a 3D perspective of maps).

In the end, all these bumps helped out when I wanted to sell the boat in the dead of winter. I actually made my money back and then some…plus it sold almost the second it went on the market.

Photo by thomaspurves

3. The water can be a real scary place, or not

I can’t actually swim. Sure, I can doggy paddle and I can crank it underwater with the best of them, but as far as over-handed swimming, I’m no champ.

One reason I bought a boat was to overcome my fear of the water. What I slowly learned over the Chicago boating season was that the more you are in the water, the more comfortable you become.

Before long, I was diving off my bow, donning snorkel gear and navigating my way around the bottom of the boat (while in the middle of Lake Michigan, mind you) just to feel her smooth lines and search for imperfections. I became friendly with all the little creatures that called my boat home (hungry birds and trillions of spiders mostly), and come summers end, I was the master of my own little water domain.

4. Expect deep envy from everyone you know

Share with anyone that you own a sailboat and the same thing will happen: wide-eyes, open mouth, insane jealousy. People think that you have to be loaded or a master captain, but not so. It’s all about gathering up a big pile of courage.

It’s all about gathering up a big pile of courage.

Boating turns to fun on the water once you learn how to read the wind and situate the sails based on that reading. A couple of classes with an instructor (on your own boat) are the key to becoming at ease with what you’ve just done (dropped 10k on a piece of fiberglass) and once you get the hang of sailing, it’s easy to get a party started.

Everyone wants to learn to sail and I’ve had pals who are complete novices head out into choppy waters and once I gave them a short tutorial, they practically owned the helm. When you show confidence, they gain experience and in the end, everyone feels like a badass.

Photo by Fordy

I also tapped my eco-friendly vein and bought an electric motor for my dinghy. Me and pals would load up the Cuba Libres and silently troll around the marina spying on other folks’ set-ups.

It’s almost a guarantee that anyone you take out sailing (or trolling) will end the day fueled up on stout drinks and proclaim, “I’m buying a boat!” See, sometimes you don’t have to even take the boat out of the slip to ignite the passion.

5. Money becomes liquid in the boating world

Rare is the boat that is purchased and then just ready to go. And, even if you do happen upon one, it’s beyond easy to get drop into Westmarine for a small $2 bolt and walk out two hours later with $500 worth of goodies.

The costs add up quickly when there are mechanics to pay, slip fee’s to rent, sailing lessons to take (private lessons $75/hr), gadgets to keep up with, oil changes to be maintained, gas tanks to fill up, provisions to keep stocked, solar panels to install, subscriptions to pay for and a litany of other things you want to do once you own a boat.

But that’s the beauty of it all…you don’t have to do anything. In fact, to sail, all you need is a sturdy vessel and the wind. The rest is just heart-thumping joy. The stuff that makes you feel alive and in touch with the world.

Note: If you want to get some hands on experience before spending a dime, check out the crew wanted section at You could wrangle your way into crewing in the South Pacific for some other fool who dropped his life savings on a boat—for FREE!

Community Connection

Along with Misty, several members of the Matador community sail, some just for fun and some professionally. Ross has a cool blog about sailing in San Francisco Bay with Doug, who, like Misty just bought a boat without prior sailing knowledge and went for it! Cody, a professional sailor, helped them ramp up their learning curves.

Finally, Darcey Maher is a professional sailor / boat captain, and author of the Traveler’s Notebook article How to Become a Boat Captain, which has some great additional resources for people interested in getting water time.


Editor’s note: The author is currently “this close” to upgrading to a 32 ft. beauty ( tucked into a small bay in Central America. Expect to find her there soon.

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.

  • Tim Patterson

    I love these articles Misty! You do a great job of showing just how fun, easy and cheap the nomadic life can be.

  • James M

    This is not the way to learn to sail, but you did get one bit right, starting with a SMALL boat.

    The best way to learn to sail without expending much cash is with a local sailing club, or by taking classes at a local community collage where sailing is offered. If you don’t live near the sea, or a lake where people sail, then take a couple of weeks course at some place that gives a week or two intensive teaching in sailing dingys. You learn fastest in very small sailing boats and your mistakes only get you wet, not killed.

    You will learn fastest in a small sailing dingy as part of a structured instructional program.

    Next move on to crewing on larger boats, just to find out how they work. When crewing you are learning, and some one else is paying the fright. You can also crew for different skippers to find out the different ways of running a boat. There are lots of ideas that you can learn from different skippers, who may all have there own way to do things. Everything from how to coil a rope through how to deploy an anchor or put in a reef. Ask lots of questions. Ask why all the time.

    Then you may have an idea of what sort of boat you want to purchase. Stop right there. The one thing the author got right was starting with a boat under 26′ in length. For a first yacht you should aim for something very simple, with few working parts, that is 25′ or less in length. Sail it for a session or two.

    Then you is one.

  • Misty Tosh

    Let me just share a little story with you.

    I was in Mexico in February, having a drink in a local cantina, when an old salty fella trolled by and offered to buy me and my pal another round. Of course we were in!

    Over cold Pacificos, he shared with us how he was finally living his life-long dream in his mid-60′s. He’d sold everything he owned and bought a sailboat–one that was about 45 ft–and he was just beginning the first leg of his new life path.

    Now, this man had never sailed before purchasing his big ole boat and he was dead delighted at his choice. He invited us out to his vessel the next day for a bit of snorkeling and we were excited to see what he’d gotten himself into.

    We spent the next day snorkeling off coral reefs, diving around wrecks, lounging in the sun, and listening to his hysterical tales of life on the water. He’d somehow managed to make it from Florida to Cuba to Mexico by the seat of his pants–learning along the way–and was about to leave for Guatemala for the upcoming Hurricane season.

    As we watched him putter around in his dinghy and don cumbersome snorkel and dive gear, we just laughed and swam in circles around the boat. It was one of the most enjoyable days ever and at the end of the day, as we were all showering off the stern of his boat, he said…”So, girls…do you think I did the right thing? Do you think I’m crazy for doing this/learning this so late in life?”

    We couldn’t help but slap him with mad props for living life in the biggest, most bad-ass way possible. He was so happy that someone across the board didn’t think he was nuts for not knowing a damn thing before he set out. This cat is now in Guatemala (yes, he made it with flying colors), on the Rio Dulce, living off about $200 a month and waiting on Hurricane season to pass so he can go diving in Belize. He’s happy as a clam, a sassy sailor now and full of immense confidence that he pulled it off! He has now become the teacher, instead of the student, all because he gave it a go.

    I guess what I’m trying to say is that everyone learns a different way. Some peeps don’t care for lessons in the manner you describe. Some just like to do it different…go a bit more rogue if you will.

    Whatever works for you…and in the meantime, I can’t wait to catch up with the captain in Guatemala and have a drink–toasting those in the world who see things a little off-color. What a lovely way to taste that thing called “chance”.

  • Lisa C.

    Not to discount the comment by James M., but I followed that sage advice early on in my sailing wanderlust and signed up for a sailing class. A slick $300 bought me the opportunity to become a “skipjack” (a five-session sailing 101) at a local yacht club. Armed with the eagerness of a Kindergartner, I rolled into the first three classes expecting to retain a bit of sailing basics. Instead, I was regaled in boring story after story delivered by the “captain;” a boozy blowhard who couldn’t wait to interrupt himself several times through out the session and recall rum-infused conquests at sea. At best, I learned to tie a bolen and got my 300 bones back after a disappointed call to the front office. Good for you, Misty. I learned to sail the old-fashioned way and just DID it!

  • Old Hand

    @LisaC et al.

    I grew up sailing, I traveled and raced sailboats competitively for decades and sailed at a DIV 1 varsity sailing team. I taught sailing for about five year and I have various and sundry certifications from Canadian Sailing Association and US Sailing, so FWIW I may be biased in favor of lessons.

    Sorry that your instructor was such a horrible blowhard, but in my experience (which I would immodestly say is ample) some very basic lessons are ESSENTIAL. Sailing is dangerous; don’t let anyone tell you differently. It is the one activity that has the highest possibility of getting you killed out of all watersports, especially on the open ocean. While I understand the romantic thrill of just doing it, the uninitiated face a very real learning curve as actual boat handling is the very MINIMUM that you will learn in any decent sailing course. More importantly, familiarity with tide, weather systems, wind “characteristics”, and your own personal safety-zone of competence are the real advantages of sailing classes. Boat handling (think steering and trimming sails) is the bare baseline of seamanship. To be competent and safe on the water, proper instruction is simply essential.

    Again, just my $0.02.

  • Dane

    I have to add that I have met many people who just went out and took the plunge, and many others who take the baby steps approach. It’s a qualitative judgment, but it seems to me that the folks with the deepest satisfaction are those that dove headlong into the project. James is definitely right about the wisdom of taking basic sailing lessons, but afterwards, if you still dream of your own boat, go out and do it! I learned far more in the first two months of owning my first boat, an aged Ericson 29, than I would have learned in years of sailing lessons, and I never really learned to sail until I sailed my own boat. I know a lot people who took the long, gradual approach to sailing, and far too many of them, after years of sailing, still seem to lack the confidence that only comes through doing it. The others that eventually got out and did it often lament they should have gone sooner. All the while, the loose cannons like us and ‘The Captain’ are out here having a lot of fun.

    By the way, Misty, that was a great article. You hit the nail right on the head.

  • Rob

    One thing to think about when buying a boat. Usually you get a “cruising” boat starting out. There boats often have sail-plans, rigs, and everything else designed for low-performance. People say this is “easier” but as a (student) sailboat designer and life long sailor, I would recommend you go with a “racing” setup. I’m not saying you need titanium blocks, spectra lines, and carbon sails. I’m saying that racing rigs are designed to be as efficient as possible, and even if you are using crappy blocks, stretchy lines, and blown out sails, I believe it is easier to sail a race boat then a cruiser.
    - R

  • BoatParadise Classifieds

    Useful information ..I am very happy to read this article..thanks for giving
    us this useful information. Fantastic walk-through. I appreciate this post.


  • ClosAguilera

    Great article.  I’ve also read your NGO article and it was also great.  You seem very confident about what your doing in your life and should share it with the world through vlog (video logging) on youtube.  There’s actually people with millions of subscribers sharing their lifes and making a living at the same time through youtube’s partnership program.  Great luck with the boat and NGO.

  • Guest

    Well written with infectious passion for sailing!

  • Vivian C Cielo

    i havent sleep for two nights thinking about about a new concept SAILING…..everything started with a local add, sail boat for sale hahaha sail…….i went to see it today, i want to buy it, i have not idea about sailing never did it,,,,i want to do it is my present to myself should i do it? I work to hard and raise my kids now what about me?

    • Ron | Active Planet Travels

      Just go out and do it…hell bring your kids with you! ;-)

  • Ron | Active Planet Travels

    My time for owning a sailboat is coming soon! It’s been a big dream, like many others, to just sail around the islands! :-)

  • William Brand

    Sailing is truly fun! Almost everyone loves to sail on the ocean. Owning one is already a bonus. Keep safe everyone while in the water!

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