Wintertime is the Right Time to Head to Kauai

We'll show you how to conquer Hawaii's stunning, rugged paradise.

By Marty Patail December 1, 2014 Published in the December 2014 issue of Portland Monthly

Kauai's Na Pali coast

Believe it or not, the rainiest spot in the United States is not Portland in December. 

No, to find that particular soggy bliss, you must head over the Pacific to Hawaii’s oldest and northernmost inhabited island. In its center, the towering Mount Waialeale acts as a volcanic catcher’s mitt for easterly trade winds, its steep cliffs funneling the moisture-laden air into clouds that drop 450 annual inches of warm rain onto the verdant jungle below.

This is Kauai—the so-called Garden Island, an unblemished puzzle of microclimates bursting from a patch of land roughly the size of Multnomah County. In the island’s northwest corner, the Na Pali coast’s 2,000-foot sea cliffs (above) tower over secluded beaches, accessible only by foot or by boat. To the west, Waimea Canyon carves a 10-mile-long, 3,600-foot-deep crevice of red basalt blanketed with glowing patches of green. On the island’s flatter, sunnier eastern half, the towering Wailua Falls lurks just 15 minutes from the airport, cascading close to 4,000 cubic feet per minute. Nearly half of Kauai’s 111 miles of coastline is covered with white, sandy beaches. 

We still haven’t gotten to the best part: only 69,512 people live on these 550 square miles. That’s half the population of Maui, and less than a tenth of Oahu. No building can be taller than the tallest coconut tree (approximately four stories), and more than 65 percent of the island remains inaccessible by car. No wonder that when Hollywood needs a remote backdrop, Kauai is at the top of the list: Jurassic Park, Raiders of the Lost Ark, South Pacific, and dozens more movies were filmed here. 

And with plenty of island-grown coffee, wild chickens and roosters roaming the streets, and farmers market in full swing every day, it’s a Portlander’s paradise—especially in winter, when temps “drop” to a daytime average of 79 degrees. 

Alekoko fishpond k3hwcy
Alekoko fishpond


You’ll land just feet from the ocean in Lihue, the island’s second-largest town. Shake off the six-hour flight with a bracing espresso at Art Café Hemingway, then hop aboard a two-person kayak from Outfitters Kauai in the Hule’ia River. A lazy two-mile paddle takes you past the ancient Alekoko fishpond—built, as legend has it, in a single night by the island’s first settlers—to a trailhead that leads you on a short jungle stroll to a hidden waterfall. If jet lag has you feeling sapped, just take a seat in one of Kauai Backcountry Adventures’ oversize inner tubes to explore the island’s agricultural history, racing down still-functional 19th-century irrigation ditches that nourished Kauai’s once-ubiquitous sugarcane fields. Cap off your first-day adrenaline rush by stocking up at the island’s only distillery, Koloa Rum Company, located on a former sugar plantation. 

Kalalau Trail


From Lihue, head north to Hanalei Colony Resort, where modern condos feature full kitchens and views of the Haena Bay framed by the fog-encased Mount Namahana in the background. The shared garden’s charcoal BBQs call out for lightly seasoned ahi steaks or local grass-fed beef. (Stock up at the Big Save in Hanalei.) Just a few minutes away, you’ll find the snorkeling destination of Tunnels Beach, a crescent-shaped patch of sand protected by a natural reef and dotted with underwater caverns. Lace up your hiking boots and drive north to Ke’e Beach—the farthest north your car can take you—where you can plunge deep into the heart of the island on the Kalalau Trail (above), which takes you up the Na Pali coastline along an undulating path through forests, valleys, and canyons. Just a couple of miles in, the Hanakapiai stream and beach makes an easy turnaround point, but hardy adventurers who tackle the two-day, 22-mile round-trip trek will be rewarded with a night on one of the most remote beaches in the world. Whichever you choose, recover by treating yourself to a festive happy hour poke bowl at Kalypso in Hanalei, where the bar’s owner/cook joins a live reggae band on stage on Friday nights.

Sheraton Kauai Resort


Protected from the chilly North Pacific swells, the south side of the island cultivates a more tropical vibe. Check in to the immaculately refurbished Sheraton Kauai Resort, which sits steps from palm tree–lined Poipu Beach—home to the island’s best luau on Mondays and Thursdays. It’s worth rising early to make the hour drive to Waimea Canyon before late-morning clouds settle in. Dubbed the Grand Canyon of the Pacific by Mark Twain, Waimea carves through a stunning landscape of orange- and red-hued rock formations. To traverse the canyon’s south side from above, strap on a harness with Koloa Zipline and glide through eight lines spread across the outfit’s 980 acres of forest. From November through May, humpback whales from the Gulf of Alaska splash about in the waters of Kauai (two-thirds of the North Pacific’s entire population comes to Hawaii to breed), so set sail on one of Captain Andy’s 65-foot catamarans to see the show, cocktail in hand. The four-hour sunset cruise delivers you to Na Pali coastline, a 16-mile stretch of otherworldly cliffs rising above untouched white-sand beaches—home only to dolphins, sea turtles, mountain goats, and the occasional nudist. Or, as our captain preferred to call them, the “rare two-legged red-tailed deer.” 

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