I’ve always had this feeling that I would never do much of anything if I waited until I was ready. Conventional wisdom says we are never truly ready for anything, so we might as well do it now. Stomach growling, thoughts clouded by sleep deprivation, itching the bites all over my face—I was about to put that theory to the test. 

Arriving on Kauai the night before, I was the last of our six person squad to show up at the hotel. We were sharing one bedroom, and it was standing room only. I slept outside on the patio. No tent. The mosquitos noticed immediately - and apparently put flyers out for the party.

Now, at 5am, tires rolling in the dark toward the Kalalau Trailhead, my only thought was trying to find a suitable dozing position. But crammed in the trunk between six full backpacking packs, loose camping gear, and shrinking wiggle room, sleep was out of the question. I focused on the Trail.

Kauai’s 11 mile Kalalau Trail leads from Ke’e Beach to Kalalau Beach along the Na Pali Coast. It ranks as one of those “must do” hikes for those who live to hike the world. Far from the longest, highest, or even most remote, it is never the less formidable. Traversing five valleys, the Trail terminates at Kalalau Beach, providing the only land access to this rugged and relatively untouched stretch of Kauai’s coast. And it’s dangerous.

According to a quick Google search, the Kalalau Trail is “one of the most dangerous trails in the United States." Perhaps even world. Maybe a bit hyperbole, but the Trail’s threats are many. It’s streams, which the journey requires crossing on multiple occasions, can swell to very dangerous levels with little or no warning, washing unsuspecting hikers out to sea. Rocks, crashing from cliffs, injure distracted hikers and campers below. It is exposed, narrow, and slippery. And if the Trail doesn’t kill you, the deadly riptides at Hanakapi’ai are churning in wait. 

Back home I’d made an executive decision. Mom and Dad didn’t need to know the Trail’s name. No need for them to worry. Now from my increasingly uncomfortable position in the trunk I had second thoughts. I shimmied my cell phone out  just as the tires came to a stop: No service. Too late. I’ll tell them when I get back. 

With just enough morning light too see without headlamps, I slipped on my hiking boots. They were brand new - and it struck me that this might not be the most prudent time for their first test. Running the laces through my fingers, I considered the countless times I’d advised people to break in their boots before attempting any sizable hike. Let alone a backpacking trip, on one of the World’s deadliest trails. Adding it to the mental “Too Late List,” along with the text I didn’t send to my parents, I finished lacing my boots. 

“Did anyone bring mole skin or bandaids?” I asked to no one in particular. “Nope.” Another “Too Late List” addition. Packs on, we took the obligatory six person selfie at the trail head just as the sun crested the horizon. 

There are a few ways to tackle the Kalalau Trail. You can hike 11 miles to Kalalau Beach in one push. Or you can take your time, explore the valleys, visit some waterfalls, and spend the first night at the designated "Six-Mile Campground." We chose the latter. 

Two miles in, the Trail delivers you to Hanakapi’ai beach with the option to hike an additional two miles up Hanakapi’ai Valley to Hanakapi’ai Falls. We hid our packs deep in the surrounding forest and headed up valley to the waterfall. Like many Hawaiian waterfalls, this one lives at the back of a beautiful valley, surrounded by verdant ferns, cool mist, and an emerald pool. I recalled seeing photos from when my parents were there decades ago, and it felt good that a place hadn’t changed. After pausing to take a few photos, and fuel up on dried mangos, we headed back toward the beach to rejoin the Kalalau Trail. 

Arriving at the Trail’s Six-Mile Camp mid-afternoon, I was struck by the lackluster site, especially compared to the morning’s stunning scenery. Located at valley bottom in the midst of thick vegetation, there were no views. Given our quick progress—and the stark lack of panorama—I floated the idea of continuing on to Kalalau Beach. 

Waking up to the view is my backpacking soul staple. And I was feeling surprisingly fresh after 10 miles. But chaffing and blisters had taken their toll on the group. Reminded, I glanced down at my feet – they felt great. I’d completely forgotten about my brand new boots. No blisters, no hot spots, nothing. 

We hit the Trail again at sunrise. The Trail’s second half is where you will find the infamous “Crawlers Ledge.” It, and a few other particularly narrow steep sections of the trail, are notoriously slippery when wet. Slippery enough to consider getting down on all fours and. . . yup, “crawling.” 

On a boat tour cruising the same section of coast a few months earlier, our captain idled under Crawlers Ledge to point out a number of hiking polls sprinkled across the sheer cliffs. Apparently panicked hikers had abandoned them to the tumultuous water below. The captain wrapped up the stop with an animated story about the woman’s body his crew pulled out of the ocean a few years earlier—undoubtedly a fall from Crawlers Ledge. I’d taken in his story with a grain of salt. But now, as Crawlers Ledge revealed itself from a much different angle, ‘don’t look down’ became my mantra. Luckily it hadn’t rained in days, so we passed the exposed cliff without incident. Honestly, if it weren’t for all the hype, I doubt I would have remembered to worry at all. 

A few valleys later, we ran into a couple collecting fruit. They were stark naked and brimming with hospitality - we were close. We reached Kalalau Beach shortly after, and spent the rest of the day soaking in as much paradise as possible. We set up camp in the shade overlooking the beach, freshened up in the waterfall, roasted marshmallows, and played cards under a blanket of stars so bright it hurt to stare. We only had one day. But one day is all Kalalau needs to hook you forever. Some places feel new no matter how many times I've seen them. Maybe it's because the world is always changing, and the light is always shifting. Or maybe it's because I am. All I know, is that there are some places like Kalalau that you have to experience for yourself. And as soon as you do, you know - somehow, someday, you'll be back.

We said goodbye to the beach before the sun was up and started the 11 mile trek back. The return lacked the excitement and anticipation I enjoyed on the way in, but the time and miles passed quickly. Sweat-salted and sunburned, I unlaced and removed my boots in the same place I had put them on two days earlier.  After 26 miles, multiple fumbled river crossings, and a lot of dirt, rocks, and mud, my boots no longer looked new, but I wasn't complaining. 

The car rumbled toward what I hoped was shaved ice. From the confines of the packed trunk, I located my phone and typed out a text while I waited for the service bars to emerge: “Hi mom! Sorry I didn’t text before taking off. Made it back to civilization. Talk to you soon!” I felt my phone immediately vibrate: “Please tell me you didn’t do the Kalalau Trail.” 

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