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    Home » Recipes » Cocktails » Drunken Sailor Rum Cupcakes with Pineapple Frosting

    LAST UPDATED: May 26, 2020 • FIRST PUBLISHED: August 8, 2011 By Toni Dash 27 Comments

    Drunken Sailor Rum Cupcakes with Pineapple Frosting

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    This post may include affiliate links. As an Amazon Associate I earn from qualifying purchases.

     

    rum cupcakes with pineapple frosting
     
    When I got this month’s vintage swap recipe, Sorghum Molasses Cookies, I recalled that rum is made from molasses.  This memory brought forth a retrospective of a trip I took to the South China Sea, then a still heavily pirated area, though fortunately I did not know it when I embarked on my trip.  My boss at the time, a blonde-haired blue-eyed nymph and I chartered a sailing vessel to tour the islands around Pulau Tiomin in Malaysia.  Our captain was a young American who sailed half the year in Malaysia and half the year in the Phuket Thailand.  He had a lovely Malay wife who prepared our food which was always delicious with authentic ethnic roots.
    My boss, we’ll call her ‘Val’, and I were both very inquisitive.  With each adventure we had a hundred questions about our surroundings.  ‘What do people do here for work?’  ‘How many people live on this island?’  ‘What is the main source of food?’  To which our trusty sailor guide commented little.
    We took excursions that unfolded with unplanned excitement.  A little dingy trip up an inland river that required mad machete magic to proceed even a few feet while being on the lookout for looming poisonous snakes overhead.  Shaking off the penetrating stares of locals and later being told we were the first Caucasian women they’d seen.  Stuff like that.

    This was some of the most beautiful scenery I’d ever experienced.  One night we docked in an inlet of an uninhabited island.  We were the only boat there.  The snorkeling was said to be some of the best in the world and as we prepared to go out we asked several questions about the sea life and what to watch out for.  There were no sharks, said our sailing shepherd, low currents and that was about it.  We swam off to the inner rim of the inlet to see what was there.  I spotted my first cuttlefish trilling happily through the currents like a motorized bath toy.  I spotted a long spined black sea urchin that I knew was poisonous from studying Marine Biology in college and from SCUBA diving (insert cartoon tires screeching to a halt sound track here).  Whoa, whoa, whoa….poisonous sea urchins?  Hold on, did Skippy the Sailor Boy not just tell us that there was nothing to worry about it?

    sand and pirate trinkets
    If you have ever snorkeled with intent, you know you lose yourself in the aqueous surroundings, as well as your bearings.  I surfaced to look for Val to ‘twalk amongst ourselves’ about the credibility of our guide.  I could not see her.  I had drifted very close to the inlet opening to the open sea where the current raged.  Were we to cross over and out of the calm inlet, the fight not to be pulled out into the sea would be mighty. 
    I waved at our caretakers back on the boat, trying to yell to see if they could spot Val.  Finally, eyes rolling inside my mask I swam all the way back to the boat, learned they’d not been paying any attention to us, found the binoculars to spot Val just as she was about to turn the corner to the open water.  I grabbed our Captain (did I mention as of night 2 he and his betrothed would have raucous screaming matches below deck after cordially wishing us a good night? ) and took the boat’s skiff to motor over the pull her from the brink. 
    After the rescue, our Captain thought it would be fun to go ashore to explore.  Still wanting to get Val alone to compare notes as our trip progression became more suspect, we agreed.  She and I went off to poke around one direction, the captain another.  We began to piece together how little our captain seemed to know about our surroundings.  It was not until we completed the entire trip that either of us uttered our deepest knowing; that if something were to have gone seriously wrong, we doubted he would have known what to do. 
    Still having a few days to go, we shook it off and rounded a corner to see him standing in a shallow eddy of ocean water.  He raised his hand to us to be quiet but come over.  As we neared the water’s edge we found him standing in the school of small SHARKS (yes you DO hear the tires screeching to a halt again).  Please refer to the prior paragraph where we learned there are ‘no sharks in this area’.  They WERE sand sharks which are usually fairly docile when small but they do match the genius that supposedly is not living here.
    That night after dining below deck, Val and I came up to sit aloft while our hosts screamed at the top of their lungs to each other.  While we’d been below, the inlet which had previously been ours alone had stealthily filled with a number of other sailing vessels.  Some a bit suspect looking.  Some parked a bit too close to us.  As I looked past Val’s oh-so-bright strawberry blonde mane, it gave me a shudder to be out in this dubious wilderness.
    So how does this ode-to-J. Peterman narrative relate to our recipe swap?  Pirates.  Pirates drink rum.  Well Jack Sparrow does and he’s the most enviable of pirates.  So my mind (which works very much like the children’s book ‘If You Give A Pig A Pancake’ for any familiar parents out there),  hopped from molasses, to rum, to pirates and landed on making Drunken Sailor Rum Cupcakes (did I mention our Captain boozed a lot after dinner?) with Pineapple Frosting, served with a Rum Runner (a cocktail bringing back Hemingway’esque memories of six-toed cats and  exploring the shipwreck Atocha and its treasure in Key West…..but I won’t regale with that tale today).  Put on an eye patch and take a bite. 
     
     
    run cupackes with pirate flag
     
    DRUNKEN SAILOR RUM CUPCAKES
    These cupcakes have a perfect cake consistency with the right amount of rum; you get the flavor but are not staggering away from the table after eating one.
    Ingredients:
     
    ·         3 cups gluten free or regular flour
    ·         1 1/2 cups granulated sugar
    ·         1/2 cup packed light brown sugar
    ·         2 teaspoons baking powder
    ·         1/2 teaspoon salt
    ·         1 teaspoon xanthan gum if making gluten free
    ·         1 cup (2 sticks) unsalted butter, room temperature
    ·         2/3 cup milk
    ·         1/3 cup gold or dark rum
    ·         3 eggs
     
    1.      Preheat the oven to 350 degrees.  Place cupcake papers in cupcake pan cavities.
     
    2.      Add all dry ingredients in the bowl of a mixer and mix to combine.
     
    3.      Add butter to dry ingredients and mix to combine.  The mixture will be grainy and not smooth (mixing takes a few minutes only).
     
    4.      In a separate small bowl, whisk together the milk, rum and eggs.  Pour slowly into the mixer on low speed to fully combine.  Once combined mix at medium for 2 minutes until smooth.
     
    5.      Fill cupcake cavities 2/3’s full.  Place into preheated oven on the middle shelf.  Cook for 25 minutes or until tops are golden in color and a toothpick comes out of the center clean.
     
    Yield:  24 cupcakes
     
    PINEAPPLE FROSTING
    This frosting has a great pineapple flavor with some texture from the crushed pineapple.  It complements the rum cupcakes beautifully.  The consistency of the frosting is not as thick as a traditional butter cream frosting.
    Ingredients:
    ·         1 ½ sticks (6 ounces) unsalted butter, room temperature
    ·         3 plus 1/2 cups confectioners/powdered sugar
    ·         6 tablespoons crushed pineapple, well drained
    ·         2 tablespoons pineapple juice
    ·         ¼ lemon, juiced (can be squeezed into the recipe)
     
    1.       Cream butter.
     
    2.      Slowly add sugar to butter, mixing to fully combine.
     
    3.      Place crushed pineapple in a fine mesh strainer and push with a spatula to remove juice.  This step is to ensure the crushed pineapple is not too wet going into the frosting not to produce the amount of juice called for by the recipe.
     
    4.      Add crushed pineapple, pineapple juice and lemon juice.  Mix together on low until combined. 
     
    5.      Add the 1/2 cup powdered sugar and mix to combine.  Mix at low speed to combine and then medium-high for an additional two minutes until it’s smooth.  If you find the frosting is not at a consistency of your choice you can add more powdered sugar to make it loftier though check the flavor as you add more to ensure it still tastes balanced.  It also can be refrigerated before icing cupcakes to firm it up.
     
     
    rum runner cocktail
    cocktail with orange slice

    DRUNKEN SAILOR RUM CUPCAKES with Pineapple Frosting

    These cupcakes have a perfect cake consistency with the right amount of rum; you get the flavor but are not staggering away from the table after eating one.
    5 from 2 votes
    Print Save Recipe Recipe Saved! Pin Rate
    Course: Dessert
    Cuisine: American
    Prep Time: 15 minutes
    Cook Time: 25 minutes
    Total Time: 40 minutes
    Servings: 24 cupcakes
    Calories: 147kcal
    Author: Toni Dash
    Prevent your screen from going dark

    Ingredients

    • 3 cups All Purpose Flour regular or gluten-free measure-for-measure flour blend
    • 1 1/2 cups granulated sugar
    • 1/2 cup packed light brown sugar
    • 2 teaspoons baking powder
    • 1/2 teaspoon salt
    • 1 cup (2 sticks) unsalted butter, room temperature
    • 2/3 cup milk
    • 1/3 cup gold or dark rum
    • 3 eggs

    PINEAPPLE FROSTING

    • 1 ½ sticks 6 ounces unsalted butter, room temperature
    • 3 plus 1/2 cups confectioners/powdered sugar
    • 6 tablespoons crushed pineapple well drained
    • 2 tablespoons pineapple juice
    • ¼ lemon juiced (can be squeezed into the recipe)

    Instructions

    • Preheat the oven to 350 degrees.  Place cupcake papers in cupcake pan cavities.
    • Add all dry ingredients in the bowl of a mixer and mix to combine.
    • Add butter to dry ingredients and mix to combine.  The mixture will be grainy and not smooth (mixing takes a few minutes only).
    • In a separate small bowl, whisk together the milk, rum and eggs.  Pour slowly into the mixer on low speed to fully combine.  Once combined mix at medium for 2 minutes until smooth.
    • Fill cupcake cavities 2/3’s full.  Place into preheated oven on the middle shelf.  Cook for 25 minutes or until tops are golden in color and a toothpick comes out of the center clean.

    PINEAPPLE FROSTING

    • This frosting has a great pineapple flavor with some texture from the crushed pineapple.  It complements the rum cupcakes beautifully.  The consistency of the frosting is not as thick as a traditional butter cream frosting.
    • Cream butter.
    • Slowly add sugar to butter, mixing to fully combine.
    • Place crushed pineapple in a fine mesh strainer and push with a spatula to remove juice.  This step is to ensure the crushed pineapple is not too wet going into the frosting not to produce the amount of juice called for by the recipe.
    • Add crushed pineapple, pineapple juice and lemon juice.  Mix together on low until combined.
    • Add the 1/2 cup powdered sugar and mix to combine.  Mix at low speed to combine and then medium-high for an additional two minutes until it’s smooth.  If you find the frosting is not at a consistency of your choice you can add more powdered sugar to make it loftier though check the flavor as you add more to ensure it still tastes balanced.  It also can be refrigerated before icing cupcakes to firm it up.

    Notes

    This frosting has a great pineapple flavor with some texture from the crushed pineapple.  It complements the rum cupcakes beautifully.  The consistency of the frosting is not as thick as a traditional butter cream frosting

    Nutrition

    Calories: 147kcal | Carbohydrates: 30g | Protein: 3g | Fat: 1g | Saturated Fat: 1g | Cholesterol: 21mg | Sodium: 61mg | Potassium: 81mg | Fiber: 1g | Sugar: 18g | Vitamin A: 41IU | Vitamin C: 1mg | Calcium: 32mg | Iron: 1mg
    Did you make this recipe?Mention @boulderlocavore or tag #boulderlocavore!
     
     
    RUM RUNNER
    The phrase ‘don’t drink and drive’ was absolutely derived for cocktails such as this one.  It’s delicious and tropical but with a healthy dose of alcohol.  I recommend settling in for ‘Tiki Night’ at home to enjoy!
    Ingredients:
    ·         1 ounce pineapple juice
    ·         1 ounce orange juice
    ·         1 ounce blackberry liqueur
    ·         1 ounce banana liqueur
    ·         1 ounce light rum
    ·         1 ounce dark rum
    ·         Splash of grenadine
    Fill a 16 ounce glass with ice.  Mix all ingredients in a shaker and pour over the ice.  Garnish with an orange slice.
     
    cocktail with orange slice
     
     
    As background, this recipe redo/swap idea was brought to life by Christiana of Burwell General Store upon finding a cool vintage hymnal/recipe book at a swap meet in Arizona. She had the vision of bringing those recipes back to life with a twist. We redo/swappers must change at least three things to make it our own and stay true to the intent of the recipe.  There is a growing group of international talent wielding their monthly vision in our recipe swap.  For the original recipe and to see all the creative spins for this month please click here; you will not be disappointed!  All recipes will be posted by 8 p.m. PST on Sunday August 7, 2011.
    « Mint Water and Farm Dogs
    Watermelon Mojito & other Costa Rican Cocktails (recipes) »

    ABOUT THE AUTHOR

    TONI DASH
    Toni Dash head shot

    Toni Dash, is a Certified Nutrition Coach and the writer/blogger, photographer, recipe developer and creator of Boulder Locavore®. She has been developing easy to make, well-tested recipes since 2010. Her seasonal recipes bring excitement to the dining table for both gluten-free and gluten diners. Toni has been featured in numerous publications and on culinary websites for her creative, delicious recipes and travel features. For more details, check out her About page.

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      Recipe Rating




    1. Anonymous says

      April 16, 2012 at 8:40 am

      nice

      Reply
    2. Monique says

      August 13, 2011 at 1:41 pm

      Outstanding story and what an amazing adventure. I loved the connection of molasses to rum; i didn't realize there was molasses in it. Great recipe leap!

      Reply
    3. emily says

      August 11, 2011 at 2:17 am

      Woah, you blow me away with the props… and the story. Pineapple frosting is calling my name, wonderful idea. Shiver me timbers, I think I have a cupcake to add to my must-make list!

      Reply
    4. Elyse @The Cultural Dish says

      August 10, 2011 at 2:09 pm

      This is awesome! I love rum soooo much and these cupcakes and cocktail are making me miss my trip to the bahamas where all I drank were rum runners! 🙂

      Reply
    5. pecan pie says

      August 09, 2011 at 8:01 pm

      Great storytelling! Can't wait to peruse the rest of your blog. Alas, I must skip the cocktail making, but the cupcakes and frosting look too delicious not to try. ~ thanks, tom

      Reply
    6. Carolyn says

      August 09, 2011 at 4:07 pm

      Wow. WOW! What a crazy trip, so glad you made it back alive. The cupcakes look wonderful, as does the cocktail. You'd need a few of those after a trip like that.

      Reply
    7. Kelly @ Eat Yourself Skinny says

      August 09, 2011 at 1:28 am

      5 stars
      Yummy! Cocktails and cupcakes, great combination! 🙂

      Reply
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