Pineapple Upside Down Cake #SundaySupper

The tropical flavors of summer are mixed with deep, luscious flavors of vanilla and brown sugar for a Pineapple Upside Cake that is so easy to prepare, it’ll quickly become your new go-to dessert.

Pineapple Upside Down Cake #SundaySupper - Take A Bite Out of Boca    

#SundaySupper is throwing a Virtual Summer BBQ Party and you’re all invited! Thanks to Jennie from The Messy Baker for hosting! Every week I participate in #SundaySupper, I think about what it would be like if all of us was actually getting together in person and sharing the amazing dishes we create. Can you imagine how much fun (and food) we’d have?! Well, I don’t have to imagine anymore because TONIGHT I will be sharing a real, live Sunday Supper with many members of this awesome group!

Since we’re all in Orlando this weekend for the Food and Wine Conference, those of us who are sticking around after all the conference activities are done today will be meeting up for dinner at Taverna Opa (not affiliated with the one I was recently at in Delray). I decided not to drive back to Boca until Monday morning — why trek back after a long day when I can easily stay over one more night. It’s nice not having to worry about flight schedules and do things on your own time. The beauty of attending Florida conferences!

Anyway, while I’m attending hands-on sessions, blogging seminars and eating yummy food all day, you can check out what the #SundaySupper crew has in store for our Summer BBQ Party. Naturally there will be plenty of potato and pasta salads and lots of things to throw on the grill, so I wanted to make sure we had some good dessert! Nothing screams summer more than a nice, juicy piece of fresh pineapple, especially when it’s laced with butter and brown sugar and set atop a warm vanilla cake. I just made myself so hungry for this Pineapple Upside Down. I’d never made nor eaten one before. One day I was browsing on Pinterest and came across one that looked amazing and decided right then and there that I absolutely had to have one. My roommate had a recipe from one of her old friends and we planned to make it that weekend. I couldn’t believe how easy it was — we did use boxed cake mix which definitely slashes time and effort way down. You could totally make your own vanilla cake if you wanted, but I was perfectly fine with this shortcut. 

Pineapple Upside Down Cake #SundaySupper  - Take A Bite Out of Boca

Pineapple Upside Down Cake #SundaySupper  - Take A Bite Out of Boca

Melted butter and brown sugar are topped with sliced pineapple and vanilla cake batter is poured over top. Then once the cake has baked and cooled, you’ll flip it over and see the gorgeous topping that was once submerged underneath all that cakey-goodness. The brown sugar caramelizes and forms almost like a crust, the pineapple is crisp and still retains all of its juiciness. 

Pineapple Upside Down Cake #SundaySupper - Take A Bite Out of Boca

I made the cake again the following weekend. Now that I think about it, I need to make it again. Soon. And many more times after that.

Pineapple Upside Down Cake #SundaySupper - Take A Bite Out of Boca 


[yumprint-recipe id=’10’] 

Pineapple Upside Down Cake #SundaySupper  - Take A Bite Out of Boca

Enjoy our Summer BBQ Party line-up! 



Sides and Accompaniments

Main Dishes


Sunday Supper MovementJoin the #SundaySupper conversation on twitter on Sunday! We tweet throughout the day and share recipes from all over the world. Our weekly chat starts at 7:00 pm ET. Follow the #SundaySupper hashtag and remember to include it in your tweets to join in the chat. To get more great Sunday Supper Recipes, visit our website or check out our Pinterest board.

Would you like to join the Sunday Supper Movement? It’s easy. You can sign up by clicking here: Sunday Supper Movement.


  1. says

    This looks so yummy! I’m so jealous of you and all the others at the conference, I wish I could be there. Have lots of EXTRA fun for me, will you? I hope you’ll bring this by The Yuck Stops Here this week. I can’t wait to hear all about the conference. See you soon. HUGS

  2. says

    This brings back some memories. My grandma always made pineapple upside down cake. I don’t hear it being made too often anymore. Thanks for sharing this recipe.

  3. says

    One of my family’s all-time favorite cakes! We never tire of this and I’m anxious to try your recipe Shaina!

  4. says

    Enjoy your last night in Orlando!!! I’m sorry I didn’t get a chance to hug you goodbye!!! Your upside down cake looks fabulous…it’s one of my dad’s favorites, so I’m thinking I could make him one when I’m visiting Denver next weekend!

  5. says

    Whoa. Just….whoa. That caramelization looks insanely heavenly! I’ve never for the life of me had upside-down cake, and you are hacking well into my defenses. I could really use this in my life right now–awesome Sunday Supper contribution, and it’s great to meetcha! :)

  6. says

    Wow! Isn’t it funny how food brings back a flood of memories? My Mom used to make Pineapple Upside Down cake for us when we were kids. What a great dessert. Haven’t thought of it for years. Yours looks fabulous!

  7. says

    I have sadly developed an intolerance to pineapples since getting pregnant this time, hopefully that is just a pregnancy thing and goes away after I give birth because I love pineapples and this looks so tasty.

  8. says

    I adore pineapple upside down cake. Your cake is so beautiful, becoming even more gorgeous after it’s flipped over and ready to serve! Thank you for making this for us.

  9. says

    This is a classic! I recently made one for a Mad Men series I’ve been doing and it was delicious!! : ) Yours looks great! : )

  10. Cynthia says

    Yum! I love anything with pineapple but especially upside-down cake. Such a great recipe. Thank you for Linking at the In and Out of the Kitchen Link Party. Hope to see you again next week.

  11. says

    Not sure why, but I have not made a pineapple upside down cake in years. I always loved them, need to make one room.
    Thanks for linking up to Happiness is Homemade.

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