Pineapple Pilgrimage: Transforming a Tropical Fruit into a Lifetime of Adventure

written by Alyssa DiCaterino

photo by Kristina Bakrevski Photography

Spotted a mysterious pineapple bouncing over the crowd at a festival? If so, you have experienced the beautiful mastermind that is The Pineapple Guy. The festival celebrity with his signature blue scarf, shades, iconic dance moves, and of course the glorious fruit, has turned this simple food into something every festival go-er can respect and appreciate. The loving, welcoming, happy, and kind feelings that typically come about at music festivals really shine through this man, and I had the pleasure of getting to chat with The Pineapple Guy to dig a little deeper into the heart behind the fruit.

FS: What inspired The Pineapple Guy” project? Does the symbolism of hospitality have anything to do with it?

PG: Hospitality certainly is one aspect behind the symbolism. There’s a longstanding correlation between pineapple symbolizing hospitality across numerous cultures throughout history. In the context of festivals, where this all came to life, it’s a reminder that there is a place for everyone and that we are all home when we are immersed in the music.

Looking back and connecting the dots, there were three significant moments that created the foundation for The Pineapple Guy project:

  1. Thursday, June 13, 1991 – A day that will remain vibrant in the forefront of my mind until my final days; an unusually cool summer evening in Northeastern Ohio’s Mahoning Valley – the first time I ever tasted pineapple.
  2. Insomniac Event’s EDMbiz 2014 – Still relatively young in my professional career, specifically within the music industry, I was overwhelmed with the amount of knowledge and resources packed into this annual conference preceding EDC Las Vegas. Featuring panels, presentations, and discussions of some of the biggest players in the electronic dance music space (past speakers include Pasquale Rotella, Team Hardwell, Nicole Moudaber, Above & Beyond, & Carl Cox), EDMbiz transformed my perception of the music industry and opened my eyes to some incredibly-profound opportunities.  One presentation stuck with me specifically, that being Dave Falk (VP of Marketing for 7UP at Dr Pepper Snapple Group). This was just days before unveiling their #7x7UP campaign and Stage 7 integration at EDC – an activation that has flourished while expanding to festivals like TomorrowWorld and Ultra Music Festival.  Without diving too deep, he provided tremendous insight behind 7UP’s strategy and why they chose to pursue the music festival space. Already having a fascination with digital marketing, branding, and social media, this really got my mental wheels turning.
  3. Costa Ricas Envision Festival 2015 – Being one of my first international adventures, this sustainable oasis in the Costa Rican jungle significantly shifted my perspective of the world and opened my eyes to what we’re truly capable of creating in our lives.  Pineapples are everywhere in this country. I ended up snagging one (quite literally) larger than my head over the 4-hour drive from San Jose to Uvita from a family-run stand on the side of the road. $2 for the most glorious piece of fruit on which my eyes have ever been laid. Best believe that sucker didn’t leave my side all weekend. From there the pineapple shenanigans were in full swing.

FS: Upon recognizing you at EDC Orlando, the weekend after first seeing the pineapple in action at Suwannee Hulaween, I had the utmost honor of kissing the pineapple. How many kisses has the pineapple racked up throughout his festival adventures?

PG: The honor was most certainly his. He still won’t shut up about that. I stopped keeping track of all the pineapple smooches. He’s one promiscuous piña. We’re trying to get him under control.

FS: It’s actually quite impressive how long you are able to hold that thing up in the air while dancing. Do your arms ever become fatigued? Did you have to amp up some workouts or anything to be able to do that?

PG: Surprisingly my arms have not become tired during any events, though there has been a day or two following where soreness has set in. My daily yoga practice is a huge part of my life and this consistency plays a huge role in being able to keep it held up for so long.

FS: Are there any special features you look for when picking your next pineapple? Where do you typically go to buy them?

Having learned this lesson the hard way, it’s incredibly important to find the smallest and lightest-weight pineapple available. This is the main feature I consider but I also look for one that isn’t fully ripe (so it doesn’t get mushy over a long weekend) and has a flourishing crown. Whenever possible, I also make my best efforts to buy organic and local (that’s just the hippie lib-tard in me).

FS: How many festivals have you attended with a pineapple in hand?

PG: Double digit festivals plus a lot of single-night and one-off events. Love making it out to Heart Nightclub, Do Not Sit On The Furniture, and Electric Pickle – all world-class nightclubs that book insanely good talent – in my stomping grounds of Miami when I have the chance.

FS: What festivals can we expect to see The Pineapple Guy at this year?

PG: Envision in Costa Rica is happening for sure from February 23-26. Might head to Okeechobee in Florida from there. Really torn between Lightning in a Bottle and Movement. Both are over Memorial Day Weekend at the end of May. Not sure which way I’ll turn but will definitely be at one.

I’ll be pineapplin’ around Miami Music Week for sure over March 21-26 but not sure where I’ll end up. Lots of last minute decisions. Just look for the pineapple.

FS: Any favorite music events?

PG: Where to even begin? There are so many quality events packed with world-class talent, passionately produced, and delivering an authentic message.

From events I’ve personally attended, Suwannee Hulaween (Live Oak, FL), Envision Festival (Costa Rica), III Points (Miami, FL), Symbiosis Gathering (Oakdale, CA), and Movement Electronic Music Festival (Detroit, MI) are undisputed. I’ve been fortunate to have attended Hulaween since their first year (2012) and have gone every year since. Same with III Points. Those and Envision are three festivals I will not miss as long as I have the option.

Though I haven’t been yet, some bucket list events are Fusion Festival (Germany), Oregon Eclipse (Antelope, OR), Shambhala Music Festival (British Columbia, Canada), Sonic Bloom (Walsenburg, CO), Desert Hearts Festival (Warner Springs, CA), Dirtybird Campout (Silverado, CA), Lightning in a Bottle (Bradley, CA), and Holy Ship! (I see you Pineapple Fam!).

FS: What’s the typical routine for the pineapple after a festival?

PG: It’s a tropical Thanksgiving feast with the squad. I think we can all agree that replenishing those bioavailable nutrients following a multi-day event is of the utmost importance.


FS: What does the future hold for the pineapple?

PG: Every day continues to present unique opportunities that I had previously never considered. I’m just enjoying the journey without getting caught up in expectations or a “destination”. The most humbling aspect of this endeavor is I’m not doing anything beyond just living my life with a pineapple in my hand.

The fact that it has made so many people laugh and smile is the greatest gift in the world. As long as that continues to be the case I will be doing what I’m doing. It’s amazing how much I’ve learned – and continue to learn – from this fun little project. It serves as a constant reminder to not take myself seriously and that we are all connected and together on this beautiful journey.

It’s amazing to see how many people resonate with the message and, overall, just love pineapple. The Pineapple Tribe is strength in numbers and has inspired a little side project that is in the pipeline over the coming months.

Pineapple Fam’ can stay in the loop by visiting

FS: Let’s put an end to the ongoing feud: Does pineapple belong on a pizza?

PG: Yes. With Sweet Baby Ray’s BBQ sauce, grilled chicken, and caramelized onions.

FS: Any final words?

Make America Pineapple Again.

Follow the pineapple shenanigans and connect with The Pineapple Guy on:




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