The Island of Misfit Joys

Slow way down in the 18th-century sugar mill town of Waimea. Its sleepy lifestyle is typified by the converted Waimea Plantation Cottages (, where former millworkers’ homes, although quaint and concierge-free, come replete with a full kitchen and multiple bedrooms. Go grocery shopping at nearby Ishihara Market (locals’ pricing on poke), then walk Waimea Beach fronting the expansive lawn-its stunning black-sand swath isn’t swimmable (go to nearby Salt Pond Beach instead), which is precisely why you’ll have it all to yourself.

If your priorities are swimmable beaches, guaranteed sun, and large resorts, Poipu on the south shore is your ticket. The Grand Hyatt ( is a 602-room behemoth, but it sports hands down the island’s best craggy-rock-lined, tiered pool, a great training beach for first-time surfers, and nine on-site bars and restaurants.

The flip side is Princeville to the north. The weather is more unpredictable, the beaches can be dangerous, and they roll up the carpet each night by 8:30. The draw? Anchored by Hanalei Bay and flanked by jagged verdant mountains, it’s the most beautiful place on any of the Hawaiian islands. Overlooking the ocean, the St. Regis Princeville ( takes full advantage of Instagram-worthy views from every suite, along with a swish spa that caters to its jet-set crowd.

For Vancouver residents homesick for some Jean-Georges Vongerichten, relax: the über-chef behind our Market at the Shangri-La has a very elegant room in Princeville. The Kauai Grill ( offers stellar views over Hanalei and fresh fish with JG’s signature French-Asian fusion. From pioneering chef Peter Merriman, grandfather of Hawaii’s locavore movement, there’s Merriman’s Fish House ( in Poipu, which channels a more laid-back vibe but just as masterful with the ono (aka wahoo fish).

One way Kauai is just like every other Hawaiian island? A dearth of cheap, good food. Bucking that trend in tourist haven Poipu is the slightly sketchy-looking Da Crack ( Fish tacos and burritos are made with whatever came off the boat that day, and at less than $10, they’re a welcome reminder of reality. In Princeville, Pink’s Creamery (818-824-9134) satisfies the same valuable function with its Hawaiian grilled cheese sandwiches (cheese, pineapple, pork), while the Dragon Wagon, parked at the Botanical Garden, is a mobile sushi bar from Matt Oliver, who started up not long after graduating from the Sushi Chef Institute in California. Fresh supplies from local fishermen transform into bites of tako (octopus), uku (red snapper), or crab-stuffed won tons. Josselin’s Tapas & Bar ( is all about share plates-from fresh bread to 36-hour-roasted pork belly-but it’s the tableside sangria cart that keeps you here.

Jim Moffat may have left his San Francisco restaurants and then started (and sold) Kauai’s upscale Living Foods gourmet grocery, but his stake is firmly planted in BarAcuda (, a buzzing Hanalei restaurant (local honeycomb with cheese and apples, pork belly, duck) requiring reservations-walk-ins are routinely disappointed–.

Kauai is the oldest of the Hawaiian islands, a point evident at Waimea Canyon State Park, where 5.1 million years of water erosion have left a canyon so scenic and lush that you’d be a fool not to take the 45-minute drive from Poipu to revel in its majesty. There are tons of tour operators that offer day trips to the stunning scenery on the otherwise inaccessible Na Pili Coast, but if forced joviality and crowds aren’t your thing, drive past Waimea to the Kalalau Lookout to take in the coast 4,000 feet directly below-no sing-alongs.

On the way back, beachcomb at Glass Beach, a hidden crescent tucked (rather unfortunately) behind a troika of large industrial oil tanks-but you’re here to explore, not tan, and depending on time and tides, the place is lousy with sea glass. If you strike out, worry not, you’re only a short drive from the Kauai Island Brewery & Grill ( in tiny Port Ellen, where a pint of the golden Wai’ale’ale Ale consoles.

Don’t go to Talk Story ( because it’s the westernmost bookstore in the U.S.; go to marvel at how this mini Powell’s (okay, very mini) exists in a historic speck of a town, Hanapepe, in a converted 1930s store. Browse for five minutes and you’ll be imagining what it would be like to chuck your urban life and frequent this amazing used bookshop daily.

Hanalei’s newest resident, Mark Zuckerberg, may have just scooped over 700 acres of beachfront property for more than $100 million, but you can have paradise for free at Princeville’s Hideaways Beach. The path next to the Puu Poa vacation rentals’ tennis courts looks urban enough, but this is where you start a steep descent via ropes to total seclusion and idyll.