On a Saturday in June, I found myself wide awake at 5am for the first time in… ever? I was strolling the beach with other victims of the time zone change, taking in the array of resorts that line Maui’s Kā’anapali Beach. Between the “hellos” and “alohas” I could hear the waves crashing against the rocks on the far end of the beach. As I counted down the minutes until the start of the breakfast buffet, I whispered to myself, “You made it, kid. You made it.”
It was around this time that my landlord texted, letting me know that my most recent rent check bounced. It wasn’t the first time, either. Still, a person needs vacations (even when they can’t afford one) and Maui is legendary among vacation destinations. Who can blame me for putting bankruptcy on the line for some fun? (Besides my landlord, obviously.)
The island, its beaches, and the aquamarine slice of the Pacific that surrounds Maui are all really hard to describe without sounding like a brochure. Sandy beaches, smiling families, sugary cocktails — it’s the quintessential tropical spot, the place middle American families spend their winters dreaming about. There were more athletes than sunburned midwesterners this weekend, however, as I was in town to cover the Maui Jim Ocean Shootout, a “unique, two-day ocean event” comprised entirely of sports for Australians that I’d never heard of.
NOTE 1: I didn’t know stand up paddleboarding could be competitive. Never even considered it. I just thought it was a cool thing that bored surfers invented and blonde people on Instagram made famous.
While on the island, I stayed at the Kā’anapali Beach Hotel — the perfect introduction to the Pacific Ocean lifestyle, and an experience seemingly designed by locals to maximize the amount of sheer fun you’re able to have on Hawaii’s second largest island. Activities, events, crafts, personalized songs… there’s a little something to appeal to everyone at the property (and yet still enough rum and open space for when the desire to be alone got the better of me, which was fairly often). Furthermore, such an emphasis is placed on cultural education that your vacation never really feels wasted. I found myself learning about local culture in a truly organic way and, as someone whose entire perception of the Hawaiian way of life was shaped by Lilo and Stitch and behind the scenes featurettes on the LOST DVDs, the effort that the property put into me leaving a more knowledgeable person was beyond admirable.
Being single, childless, and armed with too many drink tickets, I was drunk roughly 75% of the time I was in Maui, only furthering the weird, ecstatic, but also weirdly solemn vibe I had going. When you’re alone, Maui makes you feel introspective. I found myself alone on something called “The Big Black Rock” at 2AM one night, muttering stuff like “but I mean what is life even though, really?” while several fellow tourists nearby felt obligated to yell “Are you safe?!” and I had to be all like, “Yes, I will come down. I can see how this looks worrisome.”
I tried Tindering and Bumbling around for some company, but everyone just seemed really intent on selling me weed. Unfortunately for them, I’m a journalist and I take what I do very seriously — ultimately choosing to focus my buzz on drink tickets.
Even if I weren’t slurping down vodka sodas, I have to say that the competition was very confusing. First off, there are several different kinds of paddleboarding for some reason? (Did anyone else know this?) Secondly, I was admittedly a little slow to learn that New Zealand isn’t a territory owned by or part of Australia, they are two separate countries, both with their own representative Olympic athletes (all of whom seem good at watersports).
I think an Australian guy won the Maui Jim Shootout? It’s hard to tell and the fun of it is really more about the competition than… in my case at least… actually knowing what the hell was happening. In short: I liked watching it and I’m not sure any actual knowledge about what was happening could increase or decrease my enjoyment.
NOTE 2: Fellow black people: we need to take watersports away from these people, because I think the dude won like 75 grand.
While I didn’t understand anything anyone was doing, the Kā’anapali Beach backdrop made it look like the destination episode of every good 90s sitcom’s Hawaii episode. I loved those episodes, so I was all about it. Hospitality seems to be a major part of Hawaiian culture. When I wasn’t learning the rules to watersports, every employee at the hotel was aggressively invested in my happiness. The Ka’anapali Beach Hotel bills itself as “Hawaii’s most Hawaiian hotel,” and while I can’t confirm or deny that fact, I will say just about every one of their buildings is impossible to pronounce without sounding super offensive. Most of the activities scheduled for us (paddleboarding lessons, lei making, sailing catamarans— all of what you’d expect and a little that you wouldn’t) started at a wooden shack on the beach called the Hale Huakaʻi.
As a comedian, there’s a part of me that likes to complain about things. As a person with some sense, I recognize how awful it is to complain about things while walking along a white sand beach toward a shack where people are excited to teach you their traditional sports, with a rum punch in hand and every third person yelling “Aloha!”
So I just got contemplative and occasionally stared up at the sky, something the staff seemed to innately understand.
NOTE 3: The man who ran the Hale Huakaʻi was one of the coolest people I’ve ever met. I believe his name was Iopeka. He told me about the canoe club culture they have on the islands, where you join a club young and grow together as a team and community, forming lifelong bonds, and eventually introducing your own child to the group. Nothing funny to say about this, I just find the idea of a multi-generational sports team really cool, and I wish I had something similar growing up.
After a few days of the stumbling-around-mildly-lonely-but-also-very-happy-and-often-drunk in the tropics, I decided to check out Lahaina — the awesome little beach town closest to the Kā’anapali Beach Hotel. My #1 highlight from this excursion was the really cool tree in the middle of town that looks like the sex tree from Avatar. Highlight #2 was indulging in champagne and grocery store poke on the rocks at sunset. If nothing else, an experience like eating poke on the rocks in Lahaina is reason enough to visit Maui.
One of the most important aspects of a hotel stay is their breakfast offerings, and the Ka’anapali Beach Hotel buffet did not mess around. Now, my love for buffets is well-documented, and while I have many opinions about them, I think there are two things that are particularly important to remember: variety and maintenance. It goes without saying that the food should be good (and it was!), but not only should it be good, there should lots of different kinds of it replaced often (and there was!). I don’t know where the buffet stands relative to Native Hawaiian culture, but I was able to have miso soup, scrambled eggs, fish, and donuts on the same plate, which, coincidentally, would be my death row meal.
I wish I could list all of the things at this buffet for you, but it’d simply be unfair, and half the joy of buffet culture is the surprise. My hot take: Eat there.
As I get deeper into this piece, I can hear my editor tell me that “it’s a little rambling.” And it is. But so was my trip and so are the best beach vacations: huge breakfasts, drinks with breakfast, an hour in a kayak, watching Australia people do ocean sports, another drink… you get the idea. Kā’anapali Beach is a welcome escape from the anxiety and overcrowded city life. Even though I was alone for the trip and facing eviction (or, at the very least, late fees), the island and the immense amount of joy surrounding me made me feel less lonely, and eventually, I came to enjoy my solo trip as something more than just an introspective, navel-gazing retreat into paradise.
For me, Ka’anapali Beach is now where you go to run away from the world for a while, but in a more aspirational sense than a depressing one; sometimes a little distance is exactly what’s needed to gain the perspective necessary to get home and get motivated to earn that rent money.
Uproxx was hosted during this trip. You can read our policy on press trips here.