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    Home » Recipes » Cookies

    Gingerbread Pirate Cookies

    By Wendy Sondov · Published: Sep 15, 2017 · Modified: Mar 8, 2025 · This post may contain affiliate links · As an Amazon Associate I earn from qualifying purchases.

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    Ahoy Mateys! Celebrate International Talk like a Pirate Day this Tuesday (September 19, 2017) with this swashbuckling cookie crew! Gingerbread Pirate Cookies are a delicious reason to dig out your gingerbread men cookie cutters early.

    Ahoy Mateys! Celebrate International Talk like a Pirate Day with a swashbuckling cookie crew! Gingerbread Pirate Cookies will thrill pirate fans year round!|themondaybox.com

    One of my favorite things on Pinterest, are the pins from brilliant cookie artists who demonstrate multiple uses for one single cookie cutter. It is so easy to fill up the kitchen gadget drawer and even easier to get carried away with cookie cutters, so I love to learn how to multi-task with the cookie cutters I already own. Some creative people just have an eye for that sort of thing. It never ceases to amaze me. Though dressing a gingerbread man like a pirate doesn’t require shape-shifting magic, did you know that a gingerbread man can be turned into Rudolf, a moose, a penguin, or a shark? Take a look!

    Ahoy Mateys! Celebrate International Talk like a Pirate Day with a swashbuckling cookie crew! Gingerbread Pirate Cookies will thrill pirate fans year round!|themondaybox.com

    When I started writing The Monday Box, more than 5 years ago, my focus was solely on college care packages. I added military care packages to the mix upon request, which led to my heartwarming involvement with Soldiers Angels. Now, I have an idea for a new series of recipe posts geared toward packages for children. My own children grew up many states away from their grandparents, at a time when video calls were still science fiction. Weekly phone calls kept the loving relationships going between visits. Grandma reading a book on cassette tape was another favorite reminder of that special bond. My new series will share a children’s book and a care package worthy baked good to go with it. I am hoping that the posts will inspire intergenerational baking extravaganzas at home and help families share love, books, and cookies across the miles that separate them.

    Ahoy Mateys! Celebrate International Talk like a Pirate Day with a swashbuckling cookie crew! Gingerbread Pirate Cookies will thrill pirate fans year round!|themondaybox.com

    These Gingerbread Pirate Cookies were inspired by the book, “Gingerbread Pirates” written by Kristin Kladstrup and illustrated by Matt Tavares. Surprisingly, the publisher didn’t pounce on the opportunity to include a gingerbread recipe and market the book with a cookie cutter and sprinkles. The Monday Box is filling that gap! Though a Christmas story, this book (and the Gingerbread Pirate Cookies) are sure to delight pirate enthusiasts, young and old, year round.

    Ahoy Mateys! Celebrate International Talk like a Pirate Day with a swashbuckling cookie crew! Gingerbread Pirate Cookies will thrill pirate fans year round!|themondaybox.com

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    There is no special equipment needed for creating Gingerbread Pirate Cookies. A gingerbread cookie cutter (like this one) is all that is needed for the buccaneer crew. The captain cookie’s shape has an added hat. I cut-out a triangular hat stencil, laid it on top of the cookie cutter shape, and cut around the stencil with a knife tip. The hat and the head fuse together while baking. I used disposable decorating bags with #2 or #3 Wilton tips to pipe the icing, but the decorating is not detailed and the icing could be piped from a tiny hole cut in a plastic bag.

    Ahoy Mateys! Celebrate International Talk like a Pirate Day with a swashbuckling cookie crew! Gingerbread Pirate Cookies will thrill pirate fans year round!|themondaybox.com

    I always use this Glaze Icing Recipe to decorate sugar cookies. Unlike royal icing, which the experts use, there is no learning curve to corn syrup icing, it’s easy to make, easy to use, and actually tastes good! Preparing the icing for Gingerbread Pirate Cookies is super simple. One batch of icing, with a consistency slightly thicker than white glue, is divided into 5 colors. The white (¼ cup) can be added directly to the piping bag. The black is ¼ cup icing mixed with 1 teaspoon baking cocoa (to darken), and 2 drops Super Black food coloring gel. The remainder of the icing is divided in thirds for the red, blue, and green icing and is mixed with 2-3 drops of Super Red, Sky Blue, or Leaf Green food coloring gel. The decorated cookies should be left our overnight to dry completely before wrapping.

    Ahoy Mateys! Celebrate International Talk like a Pirate Day with a swashbuckling cookie crew! Gingerbread Pirate Cookies will thrill pirate fans year round!|themondaybox.com

    You don’t have to be a kid to get into the spirit of International Talk like a Pirate Day! Chewy and sweet, fall flavored Gingerbread Pirate Cookies are spiced with ginger and cinnamon. After one bite, don’t be surprised if you shout, “Yo, ho, ho! Blow me down! These be mighty good!”

    Ahoy Mateys! Celebrate International Talk like a Pirate Day with a swashbuckling cookie crew! Gingerbread Pirate Cookies will thrill pirate fans year round!|themondaybox.com

    MORE MOLASSES COOKIES

    Chocolate Chip Molasses Cookies are chewy cookies speckled with chopped chocolate bits.

    Gingerbread Fall Leaves are cookies decorated with sponge painted icing to look just like real colorful fall leaves.

    Pumpkin White Chocolate Chip Cookies are deliciously soft and chewy cookies with the flavors of pumpkin pie spice and creamy white chocolate chips.

    Gingerbread Pirate Cookies

    Gingerbread Pirate Cookies

    These adorable gingerbread men are dressed up like pirates!
    5 from 1 vote
    Print Rate
    Course: Dessert
    Cuisine: American
    Prep Time: 2 hours hours
    Cook Time: 10 minutes minutes
    Drying Time: 1 day day
    Total Time: 1 day day 2 hours hours 10 minutes minutes
    Servings: 32
    Calories: 234kcal
    Author: Wendy Sondov
    Adapted From: Lilaloa.com (gingerbread)

    Ingredients

    Cookies

    • 1 cup unsalted butter room temperature
    • 1 ½ cups dark brown sugar packed
    • ⅓ cup molasses
    • 2 large eggs
    • 1 tablespoon cinnamon
    • 2 teaspoons ginger
    • ¼ teaspoon salt
    • 4½ cups all-purpose flour an additional ½ cup may be needed if not chilling the dough

    Decorating

    • 4 cups confectioners’ sugar
    • 3 tablespoon milk add more to thin icing to desired consistency
    • 3 tablespoons light corn syrup
    • 1 teaspoon vanilla extract
    • Food coloring gel Super Red, Super Black, Sky Blue, Leaf Green
    • Sprinkles candy eyes, oval red nose, optional clothing sprinkles

    Instructions

    Cookies

    • Preheat oven to 350˚F. Line a baking sheet with parchment paper.
    • In the bowl of an electric mixer, cream butter and sugar. Add eggs and molasses and mix until incorporated. Stir in spices and salt.
    • Gradually add flour, 1 cup at a time, until the dough is roll-out consistency. When baking immediately, I needed 4 ½ – 5 cups. For dough that will be refrigerated overnight before baking use only 4 cups.
    • Roll ⅓ of the dough out to ¼” thickness on a lightly floured surface. Hint: Because these cookies spread minimally, cutting them out directly on the parchment paper they will be baked on, eliminates the need to transfer the cut out dough. Roll the dough out on a sheet of parchment paper the size of your cookie sheet. Cut out the cookies about 1” apart. Remove the excess dough from around the cut-out cookies (add it to the unused dough). Slide the parchment onto your cookie sheet. Repeat with the remaining dough.
    • Bake for 7-10 minutes. (Cookies will firm slightly as they cool.) Cool on baking sheet for 10 minutes before transferring to a wire rack to cool completely.

    Decorating

    • By hand or with an electric mixer, combine sugar and milk until smooth.
    • Add corn syrup and vanilla. Continue beating together until smooth and glossy. Add additional milk in teaspoon increments until desired consistency. (Icing consistency should be slightly thicker than white glue.)
    • Divide the icing for 5 colors. The white (¼ cup) can be added directly to the piping bag. Place ¼ cup of icing into a small mixing bowl for the black icing and combine with 1 teaspoon baking cocoa (to darken), and 2 drops Super Black food coloring gel. The remainder of the icing is divided into small mixing bowls in thirds for the red, blue, and green icing and each is mixed with 2-3 drops of Super Red, Sky Blue, or Leaf Green food coloring gel.
    • Place the colored icing into disposable piping bags fitted with #2 or #3 piping tips(or ziplock bags with a tiny piece of a bottom corner cut off).
    • Decorate pirate cookies with icing and sprinkles.
    • Allow to air dry overnight before wrapping. Once dry, store cookies in an airtight container at room temperature for up to 2 weeks.

    Notes

    Packing tips
    Double wrap pairs of cookies (with bottoms together) in plastic wrap or a cookie bag, then place in an airtight container or freezer weight zip lock bag.

    Nutrition

    Calories: 234kcal | Carbohydrates: 43g | Protein: 2g | Fat: 6g | Saturated Fat: 4g | Polyunsaturated Fat: 1g | Monounsaturated Fat: 2g | Trans Fat: 1g | Cholesterol: 26mg | Sodium: 30mg | Potassium: 93mg | Fiber: 1g | Sugar: 29g | Vitamin A: 195IU | Vitamin C: 1mg | Calcium: 26mg | Iron: 1mg
    Tried this Recipe? Pin it for Later!Mention @TheMondayBox or tag #themondaybox!

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    Comments

    1. Miz Helen

      September 25, 2017 at 11:49 am

      Your Gingerbread Pirate Cookies are just adorable, as only you can make them! Thanks so much for sharing with us at Full Plate Thursday. Hope you have a great week and come back to see us real soon!
      Miz Helen

      Reply
      • The Monday Box

        September 25, 2017 at 9:11 pm

        Thank you, Miz Helen! I had fun with these pirates and luckily they were beginner level decorating! Thank you for hosting Full Plate Thursday!

        Reply
    2. Reeni

      September 24, 2017 at 3:39 pm

      I love your new idea and the first book you picked! Perfect match. The cookies are so adorable - your decorating skills are superb!

      Reply
      • The Monday Box

        September 24, 2017 at 8:57 pm

        Thanks, Reeni! I love children's picture books and so many of them lend themselves to a baking project! I appreciate your enthusiasm and kind compliments!!

        Reply
    5 from 1 vote (1 rating without comment)

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    I'm Wendy, a baker, care package maker, and smile creator. On The Monday Box you’ll find care package inspiration and recipes for delicious treats that make it easy for you to share home baked love. Let’s spread happiness, one cookie at a time!

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