A Pirate Adventure

Pirate Ship Watercolor Illustration

For today’s prompt of “Sailing,” I wasn’t motivated to sketch a sailboat at first, so I thought about reinterpreting the meaning of the prompt as I’m often prone to do. As I was about to give up, the idea of pirates popped to mind and, mostly due to that little boy inside, I was far more inspired. I’ve only sketched a handful of boats in my life, and they’re not really my normal subject matter, so attempting to scribble an entire pirate’s ship was a bit more of an adventure. It was super fun, in the end, and I’m glad I pushed myself to try something a little different. I liked stories with pirates when I was a kid, but mostly because they were all the swashbuckling family-friendly stories that omitted all of the truly horrible aspects, beyond the occasional bit of scurvy. But there was no doubting they were the villains in the story, yet that made them the most interesting. Long John Silver from Treasure Island was certainly most interesting character in the book. Although it’s rather easy to stand out with a peg leg and a parrot. As I kid, I didn’t want to actually be a bad person, but pirates got all of the best lines in stories, so I did eventually want to play one on TV.

As it happened, I never became a television actor, and though I did stage plays for a time, I never got to be a pirate. I did get to play D’Artagnan once in The Three Musketeers, and learned a bit of fencing and sword play for the role, so that was pretty cool. I remember none of it today, of course, so I now live in secret hope that nobody ever challenges me to a duel. Thinking back, I do think there was definitely a moment as a kid when I thought being a pirate would be cool. They seemed so free and able to do anything they liked, including breaking a lot of rules. And as I got older, I realized that the freedom to sail the open seas, did indeed come with scurvy, so the whole prospect of actually being a pirate became much less alluring. But sometimes, I still find myself enjoying bending and breaking rules a bit. None of the golden ones that make us human, but the silly ones that were written by others before I got a chance to weigh in myself. For some reason, painting with watercolor seems to come with lots of rules, for example. And, I do break many of them, but I learned all of the rules first. I think it’s important to know and try following the rules before taking the pirate’s path.

Yet, once you feel confident in doing something the “right” way, then it’s time to travel a bit and visit someplace new. When I started sketching and painting, I was actually in between jobs so I had two full months where I had a few hours to paint each day. Then I started my new job and found myself with only 30-45 minutes per day. So, I first tried a little A6 sketchbook to keep things quick and small, but that felt a bit too constraining after awhile. Then, I switched to my current A5 sketchbook, which I love most. Instead of worrying about trying to dutifully set aside hours to practice techniques, I looked inward and realized what Dorothy realizes at the end of the Wizard of Oz. I had the power all along to come home. And home, in this case, is simply going back to the beginning to when I was a child. Each time I sit down to make something, I don’t worry about following any one technique or set of rules, I just scribble, doodle, color, like I did back then. Little Charlie knows exactly how to draw and color a pirate’s ship, after all, so I just let him. Granted, his adult self has been sketching every day now for over four years, and has a lot more practice. The combo is a magical thing indeed. And though it sort of defies the rule of always trying to move forward, it’s often an even better thing to move backward and experience the true thrill of a pirate adventure.

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About the Doodlewash

Da Vinci Paint Co.: Nickel Azo Yellow, Quinacridone Red, Cobalt Turquoise,  Cobalt Blue, Terra Cotta, and Indigo. Lamy Al-Star Safari Fountain Pen with black 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!
Pirate Ship Watercolor Illustration Sketchbook Detail
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29 Comments
  1. Sandra Strait 2 weeks ago

    Well, I don’t think pirates were ever really that free as many had the choice of walking the plank or joining the crew and other stook to piracy to avoid starving. Besides scurvy, they had hanging to look forward to, if caught. But it does make for a grand tale to think of them as Captain Jack and a free organization of like-minded souls. And I’m sure that most of them dreamed of being so. Also, as you say – they ended up with all the good lines in books and movies! That has to be worth something.

    • Author
      Charlie O'Shields 2 weeks ago

      haha! Yeah, I totally agree! 😃💕Not a life I think I want to actually live, but wow… those lines!! As an actor, you just want them! lol

  2. Mary Roff 2 weeks ago

    Wow! An amazing doodle for today! Recently saw some of the “tall ships” in harbor and of course they aren’t pirate ships as such but….the imagination does take one there.

    • Author
      Charlie O'Shields 2 weeks ago

      Thanks so much, Mary! 😃💕 hehe… I think whenever I see a tall ship like this I still would imagine pirates! hehe

  3. Mireya 2 weeks ago

    I know what you mean about letting go and simply creating. My best happens this way. I love pirates too and maybe I should use them in this set your sails on positive thinking art idea?

    • Author
      Charlie O'Shields 2 weeks ago

      Yay to that, Mireya! 😃💕 You should definitely use pirates and anything else that pops to mind! It’s the best journey ever when we don’t self-edit and let our hearts take us to where we need to go next.

  4. memadtwo 2 weeks ago

    I’m impressed. All those sails, and they’re just right! (K)

    • Author
      Charlie O'Shields 2 weeks ago

      Aww thanks so much, Kerfe! 😃💕 Glad you liked this! Yeah… I sometimes pause before trying something this complex, but then remind myself I have a solution for that! Just scribble, doodle, color that thing into existence! lol

  5. Karen Fortier 2 weeks ago

    Wow Charlie such detail in your pirate ship! I’m with Sandra, too many pirates were forced to walk the plank or got shot. Wasn’t a great place for girls so this tom boy dreamed of riding horses instead of ships.😉

    • Author
      Charlie O'Shields 2 weeks ago

      Thanks so much, Karen! 😃💕 Yeah, any dream of being a pirate was certainly a boy thing… and I’m not the kind of boy who would have ever made a proper pirate! 😊hehe

  6. Lisa 2 weeks ago

    I lived by water for a good portion of my life and I never got to go sailing. I’ve been on big ore ships, and canoes and most everything in between, but never under sail. In fact, I stood up in a wedding that was performed on a sail boat, but the wedding was done while we were tied up at the dock, then afterwards we motored around the marina before the reception at the clubhouse. One of Joe’s cousins has a car that turns into a boat. It’s pretty cool.

    • Author
      Charlie O'Shields 2 weeks ago

      Oh wow! I actually have sailed a couple of times, but I’m not remotely nautical. 😉 A car that turns into a boat sounds like an awesome thing indeed though! Love that! 😃💕

  7. Robert J. Coleman 2 weeks ago

    Great ship, letting Little Charlie’s imagination go to town with Big Charlie’s skills results in a realistic and inspired ship! Having built a few scale model ships, I’d say you got the fine details right. It’s magic indeed!

    • Author
      Charlie O'Shields 2 weeks ago

      Thanks, Bob! 😃💕That makes me so happy to hear! I’ve never made a model of a ship, so this was likely the most detailed ship yet. Glad you enjoyed it!

  8. Sharon Nolfi 2 weeks ago

    Beautiful job on the sails and riggings! A very fine pirate ship.

  9. LoriCtoo 2 weeks ago

    I think it looks like the Columbia in DL! This a beautiful ship! Good job!! When I finally let go of “what will others think of my work?” I really started enjoying sketch/painting. I do get nervous during WWCM, but by the end of the month that has gone. Another milestone. 😉

    • Author
      Charlie O'Shields 2 weeks ago

      Thanks, Lori! 😃💕Yeah, it’s tough these days as we post things online hoping people will enjoy them and then realize… oh my goodness, will they actually enjoy this? But, the real win is always that WE enjoyed making it. If that happens, others will follow!

  10. Jacob 2 weeks ago

    Yarr! Shiver me timbers! That be one grand galleon, even if it is a pirate ship. Amazing. Pirate stories always promise adventure and buried treasure, so it’s sure to be a fun journey.

    • Author
      Charlie O'Shields 2 weeks ago

      Jacob!! It’s such a gift to see you appear here! 😃❤️ Hope you’re doing well my friend!! Yay to pirate stories… who doesn’t like buried treasure? I feel like that’s the story of my life! hehe 😉

      • Jacob 2 weeks ago

        Haha, hiii Charlie! <3 It has been a while. I'm fine, just working on a video game at the moment and failing spectacularly to keep up with this place; I've made one post in six months. I don't know how you juggle all this stuff daily! I trust you are doing well too, and that World Watercolour Month was the usual triumph!

        • Author
          Charlie O'Shields 2 weeks ago

          ohhhhhh! A video game!! Love that! 😃💕I hope you’ll send me a link to play it when it’s complete! 😉 And yeah, I’m doing great and trying to resort myself after World Watercolor Month. It was a splendid month indeed! At any rate, miss you! And wish you all the best my friend! (and seriously… I want to play this game you speak of! hehe!)

          • Jacob 2 weeks ago

            Ah, glad to hear it! I missed most of it so I need to check out the hashtag and see what craziness went down. The game is called RetroMania Wrestling and should be out early next year. It’s all 2D/pixel with arcade style gameplay so hopefully will be fun, fan or not.

            Yeah, I miss you too! Keep on doodlin’ and washin’, though I’m sure that goes without saying at this point! 😉 <3

          • Author
            Charlie O'Shields 2 weeks ago

            Yeah, you should definitely check out the month… you can also see the gallery here – https://doodlewash.com/world-watercolor-month-gallery/

            Your game sounds awesome!! Definitely let me know know when it comes out! (I don’t even have your email, so send it to me via my contact form! 😉 And yeah… you’ll always find me doodlin’ and washin’… I’m a full on addict now and proud of it! lol

          • Jacob 1 week ago

            Oh wow! Look what you’ve done, Charlie!! It’s great to see it all collated like that. And here’s to addiction, well, at least where watercolour is concerned!

          • Author
            Charlie O'Shields 1 week ago

            Thanks, Jacob! 😃💕Yeah, it’s wild and wonderful to see all of the art! And humbling… hehe… it’s SO good!

  11. smzang 2 weeks ago

    Charlie says, “I had the power all along to come home. And home, in this case, is simply going back to the beginning to when I was a child.”

    I love that sailing ship. It sets my soul to singing.

    • Author
      Charlie O'Shields 2 weeks ago

      Aww thanks so much, Sarah! 😃💕Glad you liked this! I’m trying difficult things this month as a personal challenge… hehe… so, we’ll see how long that lasts! 😊

      • smzang 2 weeks ago

        Keep on keeping on, Charlie. You are blessed with special talents and we are blessed that you share them.

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