Both my parents are excellent cooks/bakers and growing up, a Pineapple Upside Down Cake was made in our cast iron skillet often. The caramelized pineapple from the brown sugar mix drizzling down the cake after inverted was a sight to behold. Loved eating a slice warm. 

Imagine my awe and delight when this Sumner on vacation, I saw the words Pineapple Upside Down Cake Martini on the menu. Yes please!

It was love at first sip! I knew I'd have to make this!

You can make it in a 9x13 pan but for me, this cake baked in cast iron, is the only way.

So, here is the cake and the martini recipes for you to enjoy by themselves or go upside down crazy and enjoy them together!!!! That's what I'm doing!!! Pineapple Paaaar-Tay!!!!

Pineapple Upside Down Cake 
1 Box Yellow Cake Mix ( I prefer Betty Crocker)
1/4 cup (half a stick) butter
1 cup packed brown sugar
1 can sliced pineapple (reserve the juice)
Maraschino Cherries

Preheat oven to 325 degrees, (350 if using a glass or light metal pan) In a 10-inch cast iron skillet or a 
9 by 13 inch cake pan over low heat, melt butter. Stir in brown sugar until well blended. Remove from heat.

 Drain canned pineapple, reserving pineapple juice (for cake batter). Arrange drained pineapple slices onto top of sugar mixture. Place a maraschino cherry in center of each slice.

Set aside until ready to pour the prepared cake batter on top.

Make cake batter as directed on box, substituting pineapple juice mixture for the water. Add water to desired amount need if not enough juice. Pour batter over pineapple and cherries.

Bake 40 to 50 minutes or until toothpick inserted in center comes out clean. Immediately run knife around side of pan to loosen cake. Place heatproof serving plate upside down onto pan; turn plate and pan over. Leave pan over cake 5 minutes so brown sugar topping can drizzle over cake; remove pan. Cool 30 minutes. Serve warm or cool


    Pineapple Upside Down Cake Martini 
    2 oz. vanilla vodka
    4 oz. pineapple juice
    1 oz. white cranberry juice
    Splash of grenadine

    Combine vodka, pineapple juice and white cranberry juice in a shaker filled with ice. Shake and pour. Add a splash of grenadine to each glass. Garnish with a cherry and or pineapple slice! Optional : Garnish rim with sugar or graham crackers.

    "Life is like a Pineapple, sweet and undefinable."
    ~Piet Hein


    1. My grandmother used to make pineapple upside cake every year for my grandfather on his birthday. She always made it in a cast iron skillet too. Yours looks delicious and brings back so many memories! And that pineapple martini... mmmm! Cheers to your Tuesday!

      1. Ahhhh I love sweet memories like that!!! After baby Girl arrives, I'll come make you a martini! ;-) Cheers to you Happy Tuesday my love!!!

    2. I love pineapple upside down cake, so this martini sounds right up my alley! Thanks for sharing, doll!

      Le Stylo Rouge

    3. That martini sounds super yummy! And I happen to have all of the ingredients on hand, so it may be making an appearance this week :)
      xoxo B | The Sequin Notebook

    4. Anonymous18.8.15

      Love this! We have a family recipe for pineapple upside down cake (we sometimes make peach too) and I could seriously eat the whole thing - so good! And a pineapple upside down cake martini??? That could get dangerous:)

    5. Oh this sounds so good!! Perfect end of summer cocktail.

    6. Oh my gosh how beautiful does this look - also not good that it's 9:00 AM and I want to drink it! xo, biana -BlovedBoston

    7. YUM! This drink looks delicious and is beautiful, almost too pretty to drink!

    8. What fun recipes! I always love the way a pineapple upside down cake looks -- it's just so pretty! And how delicious does this martini sound?! Thanks so much for sharing these recipes and Happy Tuesday!

      xo, Rachel
      A Blonde’s Moment

    9. Girl! You had me at Martini!!


    10. Want to hear something crazy? I've never had pineapple upside down cake before! It looks absolutely delicious though! I hope you're having an amazing Tuesday that will be full of cake and martinis!


    11. I have never had Pineapple Upside Down Cake! We are a huge pineapple family though! I am going to pin this. This needs to happen in the near future.

    12. I really need that cake to get in my belly right now!!! And that drink looks amazing!!!!!!!!!! Can you just send me both please? Thanks! Haha! Is it sad that I see grenadine and think it is named with me in mind?

    13. Both recipes sound amazing! Everyone knows I'll never turn down a martini lol. It's also probably been 10 years since Ive had pineapple upside down cake. Yumm!

    14. This cake looks delicious girl! I remember my mom baking pineapple upside down cakes growing up. I haven't baked one for years! Thanks for the idea and recipe!

    15. Um, you are perfect. Seriously. I wish that I lived closer to you...I would be begging on your doorstep for some cake and a drink hahaha. That drink will definitely be making it's way into my house sometime this week, that is for sure! Thanks so much for always sharing your yummy food with us! Hope you are having a wonderful week so far my gorgeous friend! XO -Kim

    16. I'll be right over for both!! I'm not a big pineapple person, but that cocktail looks amazing!!! Thank you so much for sharing!! :-)

    17. I love the sound of that martini and I would love it if you would link it up to Tipsy Tuesday at Grey is the New Black - a weekly cocktail linkup!

    18. Looks so simple and yummy! I would always order the pineapple upside down shot at bars in college -- it was my fav! I will have to try this :) Yum!!

    19. I don't think I've ever actually tried Pineapple Upside Down Cake! This one sounds amazing. I can't wait to give it a shot.

    20. This is how I make mine, lol. Never heard of the martini though, will have to try!!

    21. Hello! My dad used to make the best pineapple upside down cakes. This is a great recipe. I'm going to make it for my family in honor of him. Thanks for sharing! Pinning!

    22. It's a sugar high for adults!!! I will partake in both of those! As always you have produced another recipe that is causing my mouth to water. Thank you for linking up every week with us at #foodpornthursdays.

    23. This looks amazing!!! Seriously.. YOU ROCKED IT THIS WEEK! Thank you for linking up at the Creative K Kids’ Tasty Tuesdays! I have pinned your post to our Tasty Tuesdays Pinterest Board!! I hope to see you again this week! xo

    24. YUM, YUM, and the cake looks tasty, too!! :-)

    25. Thanks!! The martini sounds delish! I don't bake cause my hubby never likes sweets and I would have to eat it all;)


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