Nearly 16,000 feet below me, shimmering city lights are doing their best impersonation of stars—but they’re no match for the colorful array of real celestial lights studding an endless African night sky. Soon, I’ll get to see one of the most killer sunrises of my life. And if all goes well, shortly after that I’ll be standing atop the tallest mountain Africa.

Right now, though, I’m pretty sure this is the most miserable I’ve ever been.

Hangovers so bad you can’t see straight, dancing six ballets with cracked ribs, and that time you accidentally ate a rancid mussel don’t even come close. I feel like a stapled-together collection of misery-wrapped appendages, complete with a half-frozen, snotty waterfall trickling down my face. Why on Earth did this seem like a good idea? It’s way below freezing out, and we’re so high up the air is too thin to quickly fuel a fresh package of oxygen-burning hand warmers.

One breath per movement. One foot in front of the other. Just keep moving.

Adding insult to injury are relentless gusts of hurricane-force winds knocking me off the steep, gravelly trail, sometimes causing a frustrating backward slide. And despite the multiple doses of Kaopectate, my stomach is moving in menacing ways. There will be no guide-assisted crouching behind a frozen rock, I tell my body. It’s just not going to happen.

I trudge on, partly because the thought of returning to a wind-clobbered tent on a rocky outcrop sounds even less appealing than continuing the climb to Kilimanjaro’s Uhuru Peak, which sits at 19,341 feet above sea level.

Four days ago, seven climbers and I started our trek toward the Kili summit. We’ve been following the Machame route (also known as the “Whisky Route”) up the mountain’s southern side. It’s a challenging, beautiful trail that begins in monkey-filled tropical rainforest, moves through moorland and alpine desert, and dead-ends at the summit’s glaciers. After you’ve hauled yourself up the more than 13,300 feet from the trailhead, it’s time to turn around and bomb back down the mountain in fewer than 24 hours—a daunting prospect for someone with knees as busted as mine. But climbing Kili is something I’ve wanted to do for more than a decade, and I’m betting I’ve got the gear, guides, and training to make it work.

What to Bring

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Caption: Arc'teryx Beta AR Jacket and Cerium LT Hoody: Ultralight and compressible, this down jacket was the ideal midlayer for summit night. It’s also wonderful around camp and when paired with the company's Beta AR jacket. This combo kept me shielded from some of the worst wind Kilimanjaro can offer. I knew that even if the wind blew me all the way down the mountain, at least I'd be warm, damnit. $549 jacket, $369 hoodie Josh Valcarcel/WIRED

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Caption: Black Diamond Carbon Cork Alpine Trekking Poles: If it were socially acceptable, I would never leave home without these poles. Light, with reliable flick-lock closures, these cork-handled trekking poles saved my knees from guaranteed demolition. $160 Josh Valcarcel/WIRED

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Caption: Julbo MonteRosa Glacier Glasses: These shades look bad-ass and their polarized lenses work like a charm. Removable inserts let you customize how much light hits your eyes from the side. My only regret is that Kili’s shrinking glaciers weren’t big enough to really test these things. $100 and up. Josh Valcarcel/WIRED

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Caption: Osprey Sirrus 24: There is no such thing as a perfect daypack, but this one ­with a frame that feels like it’s giving you a hug comes pretty close. It holds more than you’d think, though I’ll admit, another outside pocket or two would make it perfect. $120 Josh Valcarcel/WIRED

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Caption: Mountain Hardwear Heratio 15 Sleeping Bag: Comfortable and cozy, but not quite capable of banishing the chill on the coldest of mountain nights. Wearing multiple layers, using a cocoon liner, and tossing a few hand-warmers in helped solve that problem. Bring a bivy sack in case of extreme cold, but watch out for interior condensation that can leave you wet and shivering. $260, and $189 for the bivy Josh Valcarcel/WIRED

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Caption: Prana Hat and Black Diamond Icon Headlamp: You might look like a bit of a goof in this down hat with earflaps, but at least your head will be happy. Bonus: Its fluffiness makes sleeping extra cozy. Other necessary headgear includes a decent headlamp. Believe me, you DO NOT want to be stumbling around the "bathrooms" on Kili in the dark. They're little shops of horrors, and while it might be nice to remain blind to all that's inside, a misplaced foot is guaranteed to ruin your night. (Remember: No boots in the tent.) $36, $90 Josh Valcarcel/WIRED

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Caption: DeLorme InReach GPS/Satellite Messenger: Once you get the hang of using the keypad, sending GPS messages on the InReach is a snap. It worked like a dream on Kilimanjaro, where you're pretty much guaranteed unobstructed views of the sky after the first day. The automatic altitude tagging lends a certain oomph to messages. Bring the USB charging cable and pair it with Braven's rugged battery pack to make sure you've got enough juice for multiple days on the mountain, especially if you're tracking your route. $380, $100 Josh Valcarcel/WIRED

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Caption: Thermos 24-ounce Insulated Drink Bottle: Insulation is key on Kili, especially on summit night when your trek starts around midnight and the wind can be something fierce. The water in my backpack's bladder froze within an hour, but luckily I had an extra stash to sip from in this insulated Thermos. Drop a few flavored electrolyte tablets in to help keep your internal batteries charged. $33 Josh Valcarcel/WIRED

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Caption: Keen Durand Mid WP Hiking Boots: These boots + 6 days, 38.6 miles, and 27,000 feet of combined elevation gain and loss = two happy feet. Toenails: 10. Summit: 1. Blisters: 0. $180 Josh Valcarcel/WIRED

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Caption: Suunto Ambit3 Peak: This watch could probably hail a passing spacecraft if you asked it to. It's a bit tricky to get reliable altitude readings from (make sure to calibrate it correctly), but it will track your mileage, route, speed, and heart rate—among other things. Bring a back-up battery pack for recharging, which you'll need to do every other day or so. $500 Josh Valcarcel/WIRED

The Design Duo Behind Better Sporks and a New Olympic Torch

Now I just need to get my head in the game and convince my stomach to shut up. Thankfully, after much complaining, my gut relents. But like a cranky toddler, it rewards me with vague, persistent nausea instead of alarming rumbles. Unlike shitting your pants, though, vomiting on the trail is totally acceptable (and expected). Our guides euphemistically refer to this as “smiling on the ground.”

There really is nothing less sexy than summit night on Kilimanjaro.

The climb to Uhuru Peak, located on the mountain’s dormant volcanic cone Kibo, has the reputation of being “a walk-up.” It’s a non-technical hike, meaning that reasonably fit people can reach the summit without specialized gear or training. But just because it’s called a walk-up doesn’t mean you can simply walk up.

“Ignore the sound of people retching and sobbing and remember to keep your pace constant and very slow,” is the slightly hyperbolic description from Henry Stedman’s guide to climbing the mountain. He’s describing the section of trail we’re about to encounter—the ridiculously steep, slippery approach to Stella Point, the spot at 18,652 feet where the trail deposits climbers on the crater rim. “The gradient up to now has been steep, but this last scree slope takes the biscuit; in fact it takes the entire tin,” he writes.

Don’t look up the trail. I’d tried that once and the trail was so steep and long that it was tough to separate climbers’ headlamps from the stars in the African sky.

Our summit assault began from Barafu (“ice” in Swahili) base camp, at 15,300 feet, just after midnight. An hour earlier, I’d rolled out of my sleeping bag, piled on about seven different layers of clothing and shuffled into our mess tent holding a headlamp in one hand and a daypack in the other and looking mildly panicked. Then off we went, eight climbers plus six G-Adventures guides, trekking extremely pole pole (slowly slowly) up the 5-kilometer trail to the peak.

We only had about 1.2 vertical kilometers to ascend, which really isn’t that much in the context of mountain climbing. NBD.

“Pole pole bila kelele, mpaka kwenye kilele,” I told myself. The Swahili phrase means “slowly, quietly to the summit,” and that was very much what I intended to do.

Sometime around 3am or 4am (excavating my watch from beneath my massive, insulated gloves would be nearly impossible, so I’m guessing) one of our guides grabbed my pack and hoisted it onto his shoulders. I was getting tired, and the guides could tell. From then on, Aboo would periodically turn around so I could awkwardly fish out my water hose and sip from it, and when that froze, he’d unscrew my insulated water bottle so I could drink from that instead.