First Cruise/First passage

My first sailing experience

Trying to capture the weather and waves

No problem! It’s cool!

My naive enthusiasm and cluelessness must have been painfully obvious to my boyfriend Ken (now my husband – so you know this story has a happy ending)… He had been on the water his whole life: surfing, boating, sailing, diving, even his day job involves him being on a boat most of the time. I considered myself pretty adventurous… but in a very “landlubber” way. Muscle cars, dirt bikes, motorcycles, off roading, rock concerts, mosh pits. Pretty fearless, right? There’s no way a little sailboat ride would be a problem.

When we first started working on FILTHY OAR  in the yard
Her new color
Captain Ken: taken when we first motored out of the yard’s dock

I guess the first clue that I had no clue was while looking for our first sailboat, everything in our price range needed work. Lots of work… it seemed overwhelming, but we eventually found a 27′ 1977 Canadian Sailcraft.

Before we could move her to the marina we wanted she needed some attention. Bottom job, paint, all new through hulls, valves, a few blister repairs… you get the idea. The previous owner (who used her as an apartment) was even kind enough to leave us a microwave with an old dried up hot dog in it!

She spent about five weeks on the hard, and we spent nearly every free moment painting, cleaning, sweating, cursing, but in the end so proud of how great she looked when we were done!

We re-named her the Filthy Oar (it was a tongue in cheek play on words, and the Coast Guard even stopped us once because they just had to know what kind of people would be aboard a boat with a name like that)!

I figured at this point we were ready to go! And bless Ken’s heart, he allowed me to feel like we just had a few more little things to do…

The weekend we planned to sail her from the boat yard to the marina was forecast to be stormy. Ken sweetly reminded me that it would be “a little rough and very wet” for the journey. No problem! I’m not worried in the least…We figured there was a chance we could make the 50 mile trip in one day, but allowed for two. We motored through the channels for quite some time finally getting into Lake Ponchatrain.

I was blissfully unaware of just how exciting this journey would be as I chattered on about how the sun was out and tried to figure out steering with a tiller.

Me learning to use the tiller with the ominous sky building behind me

As the day went on, Poseidon’s mood turned… we faced a tremendous head current and our little 8HP motor was struggling. We caught up to a group of beautiful sailboats, all under full sail (while we still motored, not fully trusting the lines and rigging yet). I waved enthusiastically to our fellow boaters and studied their heel angles, their witty names and their full crews.

They looked at us a little strangely, and only later did it occur to us that we had intruded on an actual sailboat race! Imagine what they were thinking as this little jalopy boat cruised into their “pod” not even bothering to raise her sails. We still laugh about it.

Time to hoist the sails! Ken went forward and attached the hank on jib. He tried to explain turning into the wind so the sails could be raised. Ummm… ok. I was able to figure out when the wind was in my face, but keeping the boat in that direction while the increasingly angry water and winds jostled us around was tougher than I thought. He patiently instructed me on windward and leeward (please – just say left or right), on reading the water (looks dark and murky to me), figuring out direction (again, left or right). With only a hand held GPS and hand held radio for electronics, I was completely lost. And then the skies opened up…

I found seasickness was only a problem if I went down into the cabin, so I stayed in the open cockpit with Captain Ken. The rain stung, and with no reefing lines in the sails, we had no way to reef… so the toe rail spent some time buried in the water and I spent some time sliding off the seat. The winds were unpredictable and we had more than a few unexpected jibes so remembering to keep my head clear of the boom just added to the list of things I was trying to jam into my sailing database.

We decided to anchor for the night by Half Moon Island in the Mississippi Sound. Ken yelled over the howling wind and driving rain to point into the wind, back up, go forward, while setting the anchor. Somehow, he got it set and we could settle in for the night… right… In his usual calm manner, he made us soup (which my slight seasickness and claustrophobia made impossible to enjoy). Side note: if you are claustrophobic you’ll need to conquer or at least control that on a small sailboat.

Sleeping was yet another difficult task. Not understanding shipping channels and depth of water, all I could imagine was being run over by a barge in the middle of the night or smacked into by a whale – both scenarios were not even possible where we were anchored, but what did I know? My fears were getting the best of me. Needless to say, not one moment of sleep was had.

Poseidon did give us a few hours of calm, during which time a flock of seagulls hovered at our stern illuminated by the red light of a headlamp Ken was wearing! Beeping and flapping madly, seeming to look into the companionway at me, kind of funny, kind of weird, kind of creepy…but the entertainment was short lived, as the winds picked up, the rain started again and the boat rocked and rolled. I can still hear the sound of the wind blowing angrily through the rigging, and it’s a sound that still unnerves me a bit today.

Morning brought more of the same and threw in some lightning for good measure. Hauling the anchor almost proved to be my breaking point. Again, Ken yelling over the wind for me to turn windward or leeward (right or left!!!!), and each time the bow plunged under water, I envisioned that would be the time Ken would be washed overboard and I would have absolutely no idea what to do.

He told me later, looking back at my face during this whole anchor raising fiasco, it hurt his heart to see the fear, frustration and confusion I was feeling. He figured at that point I was done with this sailing business and we had just blown our entire savings on a boat that I might never step foot on again…

Once on the move, we raised the sails again, and something kind of cool happened! We caught a strong wind just right, and we settled into a steep heel angle, buried the port rail and the Filthy Oar sailed! We sailed beautifully and were excited that our little 6,600 lb. sailboat with her fin keel hauled through the water and displayed her stout craftsmanship!

Finally, I was smiling again. Suddenly I wasn’t a useless crew member but a sailing enthusiast! I was trying to use all the lingo Ken had tried to teach me, snapped photos, went on and on about the wind in my face and the water soaking me to the bone like an old salty sailor…

And then… POW! Let me share that being hit in the face with a mainsheet traveler car that broke off the end of its track will tighten you up real quick. Just when I thought I might be having fun…

Our final task of docking brought me a whole new feeling of ineptitude… after bobbing around (well, more like being tossed around) waiting for enough of a break in the weather to safely navigate into the marina while lightning cracked all around us (I was pretty sure we would meet our demise being barbequed just outside of the Long Beach, MS marina), we got our chance to motor in and find our slip.

Ken sent me forward and gave instruction on getting a line on the dock piling. I was kneeling on the bow with a mound of line in my lap, soaked, exhausted, frustrated and pretty much envisioning the calamity of us plowing into the dock while I was tangled up in a heap of line.

Then, as if the Gods were finally feeling sorry for me, a smiling, thin, tan, friendly fellow appeared on the pier next to us. “Hi there! Y’all need some help?” Without hesitating, I tossed him the mass of tangled line in my lap. He grabbed it like a pro and helped us get tied up. Who hangs out on the dock in a lightning storm waiting for wayward sailors? That guy! Thank you, Poseidon. As an offering I’ll pour some rum into the sea (if I ever get on this boat again).


In the following year, Ol’ Filthy was pretty much redone top to bottom, starting with the mainsheet traveler that had dealt me the rude uppercut. She became our very favorite friend. Weekends were always spent with her. I got cool gifts like foul weather gear, boat shoes, turks head bracelets, fast-dry clothes, brass bells… I sewed all new cushion covers, organized, varnished, and most importantly fell in love with sailing!

We’ve gone sailing in not-so-nice weather, and I actually felt confident that no one would fall overboard and we wouldn’t be sunk by barges or whales. No one was more surprised by that than me.

We’ve moved on from the Filthy Oar and have embarked on our future home, Makana, a 1983 38′ Morgan.

MAKANA at the dock

MAKANA Maiden Voyage

We’ve downsized our belongings and upgraded our new vessel. She will be a full time liveaboard in three years, and a full time cruiser in five. Gifts consist of “things we need for the boat”. Financial planning revolves around setting ourselves up for cruising the Caribbean.

I read and research, organize and plan, add to my “boat music” playlist and can mix a mean rum drink! We take our friends out and I hoist sails and work lines like I actually might know what I’m doing. While Ken attends to safety, mechanical, structural and rigging aspects, I work on creature comforts and cosmetics.

And although my skills and confidence have improved tremendously, I’m pretty sure that naive (but determined) sailor is who I really am!

About Tracy Mazzeo

I reside in Louisiana with my husband Ken and stepson near the Mississippi Gulf Coast and we take every opportunity to sail our Morgan 384 while we continue to upgrade her for full time cruising. I’m continuing to research and plan for creature comforts and have become slightly more confident in my sailing and docking skills. I guess you could say I’ve been promoted to First Mate! I still enjoy a good rock concert too.

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4 comments to My first sailing experience

  • Lori Bolden

    Oh my gosh! If I could stop laughing long enough, I would feel a little empathy for your phobias while transitioning into a sailor. Girl, you crack me up to the point that I had to stop reading for a minute. Wonderful story. You brought us there and put is right in the midst of the tumultuous travels. Congrats on your new adventure and it appears that you have embarked on a journey to live a beautiful life with your Captain Ken.

  • Jodi

    I am sailor through the words of Tracy…Great job making feel as though I was right there. Look forward to hearing about the new boat.

  • Jill

    That was great!!! I had a similar experience as you, with a husband who grew up on the water and boating. I had no experience when we bought our first sailboat, a Grampian 26.
    The first time we sailed was very windy, when that boat heeled over I really thought we were going to die! I still get a little nervous on very windy days, but we are on our second sailboat, a Gulfstar 37.

  • Tracy Mazzeo

    Thank you for the kind words, Ladies! Jill, we actually looked at a Grampian before we bought Filthy Oar! It looks like we have both come a long way! :)

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