Vagabond Tales: Setting Sail For The Most Remote Place On Earth

There is a bit of contention with regards to where exactly the most remote place on Earth actually is.

Most lists you encounter will feature the usual suspects such as the island of Tristan da Cunha, the village of Ittoqqortoormiit (Greenland), the Svalbard archipelago (Norway) and McMurdo Station (Antarctica). Just last month we published one such list right here on Gadling.

Nevertheless, in every one of these lists there is one place, which is always conspicuously absent.

No, it’s not the town of La Rinconada, Peru, a mining outpost, which sits 17,000 feet up on the slopes of a permanent glacier. That’s usually on there too. Geographically speaking, the world’s most isolated landmass is a place known as…


Wait. What? Hawaii? There are over 4 million visitors a year to the island of Oahu alone. I can watch a bad movie on the airplane, take a nap, and I’m there. How is Hawaii remote?

While many of the places mentioned above may be unique in their inaccessibility, technically, the Hawaiian Islands are the most isolated populated landmass found anywhere on the planet, with the closest point of continental land being 2,400 miles away (California).

Given the fact that Hawaii is accessible, I surmise, must be the reason it never makes the list of places, which are “remote.”

What if, however, you set out to experience one of the least accessible places in all of Hawaii. The foremost outpost in the world’s most isolated island chain? A place where there are no hotels, no roads, or really any trails. A place you cannot fly to, drive to, or barely even walk to. What sort of remoteness exists out there?

That was the question in everyone’s mind as we set sail for the north shore of Molokai on a catamaran loaded with surfboards, beer and a number of lingering unknowns.

To begin with, there are a number of factors, which contribute to Molokai’s north shore being so remote.

For one, most of the north shore is occupied by vertical slabs of foliage, which collectively form the tallest sea cliffs in the world. Created by the collapse of the eastern Moloka’i volcanic caldera, the force of the landslide was so strong that rubble from the seismic event was jettisoned 120 miles north along the ocean floor – the last 80 of which were actually uphill. Though geologists estimate this cataclysmic event to have occurred 1.4 million years ago, as recently as 1999 a massive avalanche of rubble cascaded down from 2,500 feet in elevation, which was strong enough to create six new acres of land.


Exploding over 3,600 vertical feet directly from the sea, the cliffs render the majority of the coastline inaccessible to human landfall. In fact, there are only three access points along the entire coastline, which could potentially provide places to land – Pelekunu, Wailau and Papalaua valleys.

One of these would hopefully provide a safe anchorage, but which, however, we still didn’t know.

The other issue with accessing the northern coastline of Moloka’i is that the waves are almost always too large to approach the island safely. During the winter months the surf can frequently be in excess of 30 feet, and in summer the 30-40 knot trade winds whip up wind swell, which reaches 12-15 feet and turns the shoreline into a cauldron of whitewater.

To put it simply, rarely is there a calm time to be back here.

Which is why when the weather forecast starts calling for light southerly winds and just enough surf to warrant packing boards, you find your closest friend with a boat, buy the grocery store out of beer and set sail for one of the most remote – and beautiful – places on Planet Earth.

To reach the north shore of Molokai from neighboring Maui you first must cross the 9-mile Pailolo Channel, a Hawaiian word, which means “crazy fisherman” and references those who are crazy enough to fish the channel in the throes of her roughest seas.

With the favorable weather on this particular trip, however, crossing the Pailolo is scarcely a challenge and the island looms larger with each passing moment.

The first indicator you’ve successfully crossed the Pailolo is when you round the backside of Moku Ho’oniki rock, an offshore promontory, which was actually used as a bombing range during World War II. Looming a mile offshore of mainland Moloka’i, “Moku” is now a seabird sanctuary above water and a popular scuba location due to the scalloped hammerheads, which circle below.

With fishing lines trolling the deep waters we adjust our heading to point towards Halawa Valley, a deep cut in the mountainside many historians believe was the site of original Moloka’i settlement sometime around 650 A.D.

Despite being the island’s first settlement, however, Halawa today is still sparsely inhabited. The handful of families living in the valley subsist mostly off of the land, and generators provide what little electricity is needed. For traditional visitors to Moloka’i Halawa Valley also marks the end of the paved highway; unless you have some boots or a boat, Halawa is going to be the end of the road.

Putting Halawa in the non-existent rear-view mirror we change tacks again and venture further into the little known. With each passing whitecap my excitement strengthens, the sound of waves slapping hulls being the only barrier to silence.

Onward we sail beneath towering promontories and past valleys, which open like gaping green time portals. Two of the valleys – Wailau and Pelekunu – feature lean-to shelters on the sandy shorelines where local families will occasionally spend entire summers.

Up until the early 1980s Pelekunu Valley was actually home to a handful of year-round residents. There are no quick jaunts to Costco back here, and no paying at Starbucks simply by swiping your iPhone. Living back here means living off the land. Pigs and crops provide nourishment on shore, and fish are gathered from the expansive blue sea. Flowing streams provide a source of fresh water, though rain is also gathered from showers, which pass on the breeze. A throwback to the ancient Hawaiian ahupua’a system of land division, all that is needed for survival is contained in this narrow segment of summit to sea.

The one thing missing, however, is modernity, a parallel reality, which now renders the valleys vacant.

With the sun disappearing behind the crest of the towering cliffs we set about searching for the evening’s safe anchorage, somewhat of an oxymoron given the area’s usual conditions. Blessed with southerly winds, which place us in a rare lee (the northeasterly trade winds in Hawaii blow 85% of the year), we find a patch of sand large enough to drop anchor and close enough to shore to surf the nearby break.

The anchor is set and one of us jumps in to ensure its dug in properly. The water is 50 feet deep and the sun is getting low. We joke that it feels sharky, with the only problem being that no one is joking. We didn’t come this far, however, to not enjoy the water. Boards are unlashed and a spear gun unsheathed, and the crew sets to work on enjoying the playground.

An hour later, with 30 waves surfed and a two-pound to’au (blacktail snapper) lying on the deck of the ship, more beers were cracked and the sun bade her final farewell over a western horizon rendered invisible by the height of the towering cliffs.

Behind us the 1,650-foot column of water known as Papalaua Falls kept a watchful eye over the campsite as sunrays were swapped for a ceiling of shooting stars.

Isolation historically has been used as a form of punishment, with authorities choosing to banish souls to the known fringes of the planet. From this vantage point, however, with favorable breezes and a gentle north swell, it’s my genuine hope to stay enveloped in the moment and never be forced to go elsewhere ever again.

Want more travel stories? Read the rest of the “Vagabond Tales” over here.