Hawaii Travel

The Maui Pineapple Tour is a life-affirming experience

The most fun you can have on Maui without drugs

Being a tourist in Hawaii can be treacherous. Visitors die here all the time because most of them either don’t understand or don’t respect how dangerous this island can be. Well, that, and a lot of them are really stupid. How stupid? There is at least 1 death every year from somebody trying to take a selfie at the peak of a ridge hike. Imagine risking your life and dying because you wanted to impress a few people on social media. (follow me @mannimal3).

Even worse than dying in Hawaii is being overcharged and underwhelmed by a tourist trap and wasting half a day bored out of your mind. Since Hawaii is beautiful outside every day all day pretty much everywhere, the quality of your excursion usually depends entirely on the tour guide and how much he/she cares about your experience.

Thankfully, tour guide Tim AKA Pineapple Tim AKA The Ginger Avenger cares a lot about your experience on the Maui Pineapple Tour. Before I describe my experience, I should provide some background on why I decided to do the most touristy thing possible after living here for 4 years. I look slightly retarded and I need to defend myself.

I was on Maui for work on a Friday and, since my favorite married couple (Tim and Diana) live in Kihei I decided to make a weekend out of it. Once I heard that Tim was a pineapple tour guide, I had to witness it for myself. We woke up on Sunday slightly hungover (this is how most of my stories begin) and drove out to Makawao to see Tim in action. Well, I wouldn’t say I was hungover but I had that weird feeling where I wasn’t exactly in pain but I felt like I had Alzheimer’s. My brain was moving like an old Macbook where the colorful spinning wheel won’t go away. It was a mixture of having a stroke and a severe learning disability.

What makes it even more fun is my anxiety and depression which are amplified x1000 because all of the defenses I’ve built up to handle them are offline when I’m hungover. I become a negative ball of anxiety that is pessimistic and resentful about everything and everyone. It’s borderline impossible for me to get out of my own head unless I have a helping hand, and most of the time I’m unable to ask for it. I’m a real joy to be around.

This train of thought led me to believe the tour would be a boring, run-of-the-mill tourist trap that was unsalvagable even with Timbo Slice at the helm. But once it began and Tim started driving/talking through the headset microphone, I knew I was in for something special. This beautiful son of a bitch guide the living shit out of a tour. He was telling us about the Maui Gold plantation history, interacting with the crowd, making jokes, just being an all-around charismatic, charming human being. I forgot how overwhelmingly positivity he can be.


I did get carried away at first when he asked our group “where do pineapples come from?” and I yelled out “Mesopotamia” which was not the right answer nor is it an actual place anymore. I couldn’t help it, I had to throw him one curveball. The whole bus was kind of confused for a second but Tim made fun of me and got the people laughing again, he’s somewhat used to my bullshit so he took it in stride.


We stop at the farm and Tim whips out a giant machete and starts slicing and dicing these delicious golden sugar bombs and feeding us one by one. He’s explaining the pineapple planting and harvesting process that is still done by hand (the planters make $80/hour, I can’t believe I paid this much attention). Other facts I recall: The top of a pineapple is called the “Padunkle” (I probably spelled that wrong), 2nd generation pineapples are the tastiest ones, and Maui Gold fields yield 30,000 pineapples per acre whereas those Dole assholes only yield 20,000 per acre. At this point, I’m so engaged it’s weird. Against all odds, I was keeping an open mind and actually having fun with it.

After the first 2 stops of eating way too many fucking pineapples (they’re nature’s junk food) he showed us some antique farm machinery that’s still in operation (it was built in 1957 how am I remembering this) and a bunch of pineapples at various stages of the growing/harvesting process. I even took a portrait mode photo of the baby pineapple because I had been transformed into a full-blown tourist. What the hell was he doing to me?


Photography is easy

My favorite part of the day came when the Red Rocket went to cut open a baby pineapple and I acted like he was murdering a child. He knew I was joking but my serious tone and objections got the rest of the tour group on my side and pretty soon everybody was yelling at him to leave the poor baby pineapple alone. I wish to God I would have gotten a picture of his reaction. No words can describe how confused he looked. It was one of the highlights of my year.

Foster child pineapple

Spared from Tim’s Bloodlust. His name was Randall and he’s already dead. Pineapples only last 9 days. 

To top things off, Tim led us through a singalong of “Pineapple Princess” and an impromptu version of “Ignition (remix)” by R. Kelly. It was above and beyond anything other tour guides would have done. He truly wanted to connect and share this experience with us and we felt that. Since he lives on Maui now, I can sometimes forget how good he is at keeping the mood light and the outlook on life positive.

I won’t spoil the end of the tour, but I will say you get a to take a free pineapple home with you. I already looked like Jason Segal in Forgetting Sarah Marshall to the rest of the tour group. The festive pineapple box made me look like the loneliest tourist on Earth at the Kahului airport. Such is life.

You don’t always know the effect you have on people. It’s impossible to see what’s going on behind somebody else’s eyes, and a simple gesture or a positive attitude can make a world of difference. To Tim, he’s being himself and making sure the good vibes are contagious to everybody around him. To me, his tour got me out of a spiral of negative thinking that would’ve taken a big watery shit all over my week. If it had been any other tour guide, I would’ve come out of the experience feeling even worse than before. But because Tim put so much effort to make sure we had a good time, I walked away feeling better about myself as a person and the world around me. It sounds over the top but it’s true. And if he can do that to me, I imagine he’s had a profound effect on others as well. Even if he doesn’t know it.

So if you’re on Maui and looking for a daytime activity, check out the Maui Pineapple Tours in Makawao. It’ll only take you 2-3 hours for the whole experience and it’s well worth it with Tim at the helm. Don’t get suckered into snorkeling where you’ll most likely drown or hiking where you’ll probably to fall off a cliff taking a selfie. Spend the day eating pineapple with Hawaii’s best pineapple tour guide. It’s worth every penny and I guarantee you’ll leave with a smile on your face.


Me leaving with a smile on my face



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