Though I love “sailboats,” our art challenge prompt for today, I don’t really have much experience with them except viewing them from afar. So, we have this quick little sketch of one for today that I wish I could hop on right now. I don’t live anywhere near an ocean, but I am surrounded by many different lakes. I no longer know anyone who lives on these lakes so I can’t invite myself over for a visit. Simply knocking on the door of stranger and asking for a ride in their sailboat would certainly be met with suspicious stares if not a call to the police. But that doesn’t mean I haven’t considered risking it in my more adventurous daydreams. When I was in high school, my best friend actually did live near the lake and had one of those little two person sailboats. I love the view of a lake, but equally they freak me out a little with their muddy nature and inability to clearly see what’s underneath. But, never being one to shy away from an adventure, when my friend suggested we go sailing I answered with an enthusiastic, “Yes!” What happened next was definitely memorable.

We wandered down the path to the dock where the little boat was waiting for us. It looked harmless and almost cute and I was excited to experience my first time on a sailboat. Getting into the boat was easy enough and soon we were drifting away from the dock and out into the lake. It was at this point that I realized I had absolutely no clue how these boats work. Do we just drift along for hours hoping a clever wind will return us back to our exact spot? Of course that wasn’t the case as there was a bit of skill involved. Skill that I had never acquired and was at the whim of my friend as he barked various instructions to me. Since my complete lack of knowledge made me rather worthless in the sailing department most of the instructions came more in the form of a command, that always sounded like “Duck!” This was because each time we shifted course, the sail would swing in a terrifying way to the other side and yank us down another direction. Within minutes, though, I was ducking like a champ and felt a little sense of victory. Until my friend declared we were going off course.

Suddenly, we were surrounded by other little sailboats with very serious looking people. I found it odd that so many folks would choose this exact moment to be out on the water until my friend clarified things by shouting, “It’s a race!” Apparently, there was a sailboat race that day and we had unintentionally entered it. My first thought should have been full on dread, but with my newly discovered confidence I simply asked, “Do you think we can win?” Though I was set to give it my all and ready to race, we were instead met with shouts that didn’t sound particularly friendly. Many included words that actually bleeped themselves out in my head. Suffice it to say, the official contestants were not pleased at all. But my friend and I just started laughing. Huge belly laughs that I can still remember today, while we desperately tried to escape the race. We finally managed our way back to the little dock and in doing so, felt like we’d actually won after all. Our smiles stayed with us that entire afternoon, creating a special kind of joy that ensured I’d never forget that time I went sailing.

About the Doodlewash

Da Vinci Paint Co.: Cobalt Turquoise, Benzimida Orange, Quinacridone Red, Nickel Azo Yellow, Terra Cotta, and Cobalt Blue. Lamy Al-Star Safari Fountain Pen with sepia ink in an A5 Hahnemühle Watercolour Book. Want to purchase a print of this doodlewash? Send me a note with a link to this post, and I’ll add it to my shop!
Day 17 - Sailboat Watercolor Painting - Doodlewash

Recommended6 recommendationsPublished in By Charlie

29 thoughts on “That Time I Went Sailing

  1. This is an absolutely hilarious story, Charlie, and I’m still grinning about it as I write. Yep, there you are, champion sailor, tacking, jibing, and ducking the boom. You’re lucky you didn’t end up in the drink, dog paddling for safety. Such a wonderful adventure definitely deserves its own Doodlewash. I bet that’s you, sitting under the striped sail,facing into the wind.

    I’m no better sailor. My parents shared a small yacht with another family. After they realized I was going to endure every experience out on the Pacific the same way – by throwing up – they let me stay home. Thank heaven. My dad and brother loved it though, and went often to fish and bobbling around on the sea. Romantic as long as you don’t get seasick.

    1. Thanks so much, Sharon! 😃💕Glad you enjoyed this story. Yeah, it was definitely an adventure. And your story is precisely the reason why I’ve never attempted a cruise… I think throwing up might become a thing during it. Best to not take chances! hehe

  2. Love your sailboat with it’s colorful sails. I’m still chuckling about your story. You are probably lucky you didn’t end up colliding with someone. People who are intent of winning a race don’t always stop when someone gets in their way!

  3. Remarkably good painting given your past. I remember going sailing on a lake when Iwasa a scout. Off we went into a total lack of wind floating 10 yards from shore. In the end we rowed back and and went home!

  4. One of my favorites for certain. I grew up on north shore Long Island where sailing was and is very popular. Loved how quiet it was on the water and the adventure of finding the wind. Liked your story. I look forward to your post every day.

    1. Thanks so wonderful to hear! Thanks, Karen! 😃💕 I’m so happy to know you enjoy my posts! Keeps me coming back with more! And yes… that stillness while finding the wind was amazing. Loved that!

  5. I love this story! I always wanted to sail too, but even though I lived by Lake Michigan, I never got the chance. Kayaking too was something I dreamed of, and never did. I canoed though, even though I was afraid constantly that we were going to tip over.😀 Maybe a houseboat?? 😂😂😂

    1. Thanks, Lisa! 😃💕 hehe… yes to a houseboat! I think that would be the best thing ever! I tried canoeing once as well and survived it, but was not very good at all. I’ve much prefer to just float along the water without having to worry about falling into it. 😉

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