STAYPINEAPPLE’S SUMMER DREAMING CONTEST

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This year we’re celebrating National Pineapple Day (June 27) all month long with our Staypineapple Summer Dreaming Contest.

With a much more fun summer on the horizon, The Staypineapple Summer Dreaming Contest aims to get travelers excited about hitting the road again. Staypineapple is challenging our friends and followers to share some of their best travel memories in Staypineapple's list of exciting destinations to inspire future adventures. Staypineapple is welcoming those who have stayed with us before and new friends alike to join in the fun!

When you book a vacation with Staypineapple, you are not just buying a place to sleep. You are purchasing an experience that will live far beyond the nights’ stay. We inspire out of the ordinary experiences…experiences that create long-lasting memories with the people closest to you while exploring your way through a new city, or a beloved place you keep coming back to.

Sure, The Naked Experience, our incredible Everything People, and Dash the Pineapple Pup are memorable and fun. But we want you to get out and explore and see how many summer dreaming memories and how much fun you can create throughout our extraordinary locations.

That's why we are gifting the winner of our Summer Dreaming Contest one of our iconic black and yellow beach cruiser bicycles, perfect for exploring in style.

The pineapple challenge is on!! 

Here’s all you need to do:

  1. Share a photo on Instagram of you in any of our seven cities, including New York, Chicago, San Francisco, Boston, Seattle, Portland, and San Diego.

  2. Caption it with your favorite vacation experience.

  3. Tag  @staypineapple and use #StaypineappleSummerDreaming to be entered to win one of our beach cruiser bicycles.

  4. Follow @Staypineapple on Instagram.

Multiple entries are allowed and encouraged. The winner will be announced on June 30, 2021.

Show us how you Pineapple!!

TERMS & CONDITIONS