Around the beginnings of the worst period of my life, which some like to pretty up with the mellifluous term “adolescence,” I convinced my parents (probably with a lot of tears and screaming) that my purple Huffy with the bread-basket seat would no longer suffice, and turned them toward a flash white/hot pink/bright orange 10-speed mountain bike that I got for Christmas, or a birthday, or one of those holidays falling in that week between December 25 and January 1 that everyone likes to ball into one.

The choice of bike was ironic for several reasons, number one being that in Moorhead, Minnesota, or Fargo, North Dakota, or anywhere in about a 600-mile radius for that matter, there are no mountains. (The closest thing might be that manmade hill in Alexandria where our school trips went for "downhill skiing," but I'm not sure that really counts.) Furthermore, being a mere dabbler in neighborhood bike-riding, there was really no need to have more than one, okay, maybe two, speeds, besides the fact that it made the cool sound when you changed gears.

But as a junior-high-school prat, you absolutely had to be riding wheels with the thickness of two normal tires, studded with treads like those trail-runner New Balances have on the bottom, or be banished from the cool crowd for good. So I raced that bike around the Big Block – from our corner on 37th Avenue and 4th Street, down to the circular house - always the creepiest visit on Halloween, past my crush’s house, and back home, keeping up with the best of them. I'm surprised there's not three-inch deep rut ringing the block.

But that all was flat land. The most strenuous biking I ever did on my 10-speed was getting it to the top of the neighborhood park's sledding hill and barreling back down. Maybe some paved paths through the Boundary Waters National Park with the fam. But mostly, it was ridden straight across the Midwest's characteristic flatness.

Short story long, I don’t think I ever associated the term “mountain biking” with actual mountains. “Mountain biking” meant riding a cool-looking bike. The term “mountain” was all out lost on me. Which is my explanation for how I was duped, and why, on arrival to Waiheke Island, a 35-min. ferry ride from Auckland into the Hauraki Gulf, I walked straight to the bike rental shop, slapped down $30, put on the required nerdy-looking helmet with a scoff, and proceeded to have an ass-busting, calf-cramping ride suited more to Lance Armstrong than a Midwestern occasional-cyclist.

The locals will tell you that Waiheke has become “yet another Auckland suburb.” Once a home for secluded, mild-lifestylers and a few vineyard owners, the population has expanded and the small baches are being torn down and replaced by places that require narration by MTV Cribs. On top of that, the ferries cart city-folk out and back seven days a week, so it really has become an extension of the city. It’s a nice place, some beautiful white-sand beaches, but if you’re not big into wine (like myself - I’m happy with a $5 bottle from Osco Drug), there’s not a whole lot going on.

But I wanted to see it. And since it’s about 12km end to end, I thought biking it would be the most efficient way to sample its entirety.

“Biking Waiheke,” coworkers said, followed by that unnerving Kiwi “Mmmmmmm.” I didn’t notice the mmm-ing habit until my American expat coworker pointed it out. Now it bugs the shit out of me. It’s not one of those obvious American Hms (as in, I know what you’re saying, and I think it’s the dumbest idea I’ve ever heard), or the less obvious (What the f---? I have no clue what you’re talking about). It’s more of an “I know something you don’t” kind of vocal gesture. But I didn’t think to question…

It would’ve been as good a time as any for someone to helpfully suggest, “Hey, the island’s really hilly, are you sure you want to bike?” Instead, I repeatedly got a “Good on ya!” (Or is it “Get on ya”? Don’t know, but it’s the equivalent of an encouraging punch on the shoulder.) I took it to mean, good for you, going out for a nice bike ride instead of loafing at home on the couch. Maybe they thought that after the bungy jump, the sky dive, the snorkel trip, the surf lesson, I was looking for a new challenge. Maybe my gut-hiding clothing had them fooled that I’m in some sort of shape, and could handle such a ride. Or, maybe they were just laughing behind my back.

Okay, so Waiheke’s not exactly the Alps. And its terrain looks harmless enough at first. Especially since the view from the bike rental shack towards town looks decievingly flat. It’s a nicely paved road, surrounded by palm trees and ferns, tropical plants and flowers. A soothing, relaxing setting. But not five minutes in, I was breathing hard and sweating. By minute eight, panting and swearing. And by minute 10, I was off my bike, walking it up the first of about 5,000 hills that made me ashamed of my lack of stamina.

On top of the physical exertion, there was the added hurdle of trying not to get hit by the non-ceasing parade of vehicles. Now, I survived biking the streets of Paris, a trip that culminated in a Mr. Toad’s-Wild-Ride escapade down the Champs D’Elysee. So you’d think maneuvering this small island, home to only a handful of cars, would be a breeze. You’d think that “Auckland’s escape” would have a less frantic pace of life, especially since the most popular thing to do on the island is sit back and wait for the latest vintage to age.

Not so, my friend. Apparently city speed limits don’t apply offshore. Cars seemed to be aiming for an inch off my kneecap, and I swear I actually heard them speed up before passing me. And while my bike had the same handy “Stay to the Left” sticker as my rental car’s dash, it was hard to stay close to the line, for fear of skimming down the steep drop-off and into the ditch - and at times, down the face of a (semi)mountain.

As an added slap in the face, every time my ass started burning so badly I had to get off and push up a hill, the island's public bus, filled with fat ‘n happy ‘n drunk people, would cruelly and effortlessly cruise by, nearly throwing me and my bike into the trees.

The first beach I came to, I dropped my bike, stripped down to my suit, and walked straight into the water. It was the perfect temperature, better even than the air, which was bringing in a cool wind off the sea. After drying off in the sun, I felt refreshed and ready to hit the hills once more.

That lasted about 2 minutes. And it was at least 30 to the next beach.

Pedal, pedal, pedal, peeter out, jump off, push. Get on, pedal, pedal, slow to the point of tipping, jump off, push. With a lot of swearing sprinkled in. The only benefit of the climbing was a nice view from the top—vineyards and grasslands, baches and beaches. Oh, and the fact that for every push uphill, there was a sweet ride down.

Finally, to beach No. 2. Locked my bike to a landlocked boat and set off to explore. Climbed some rocks to the West, and stumbled right onto Nudie Beach. I’ve always been mad at myself for not partaking in the naked action at Mykonos’ beach – when in Rome, right? Or Greece, whatever. But as I considered shedding all, I realized that I was surrounded by old men. There were some middle-aged women at the top of the beach – some herding about small children in suits, while their own skin was hanging out, which I found a little creepy - but it was mostly geezery men. Loose skin, and old balls…gross. And a lot of hair. An uncomfortable amount of hair, to tell you the truth. And then the sun went behind a large gray cloud, and that killed it. Maybe I’ll get another go on Mykonos someday.

Besides, common courtesy at the nudist beach baffles me. I understand wanting to enjoy the experience au naturel. I fully understand not wanting tan lines. But how do you deal with other people? Do you make eye contact, or is that creepy? You’d think people partaking would have some sliver of exhibitionist in them, but obviously it’s rude to stare. But how can you not? They’re naked! I got uncomfortable trying to figure it out, and with nowhere else to go, I headed back to the dreaded bike.

Back on the butt-bruising seat. Back up the hills. According to the rules of physics, you’d think that any hill would be equidistant from bottom to top as top to bottom, right? Not so on Waiheke, where the Up route is always 100 times longer than the Down.

I finished my island loop, with a couple of shortcuts that looked like wise choices from my map, but, I didn’t think until later, maybe were not recommended because of their inclines. Well, live and learn. Mountain bikes are actually made for mountains. Or at least serious hills. My muscle memory won’t be forgetting this lesson any time soon.