The veranda at the St. Regis overlooking Hanalei Bay and the Napali Coast
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View of Hanalei Bay from your tub at the St. Regis
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Wishing Well Shave Ice truck
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Kauai is arguably the most relaxed of the main Hawaiian islands. Whereas Oahu is lined with towering resorts and condos, Kauai’s buildings max out at 55 feet. And in lieu of thriving nightlife like Maui, the most action you’ll find here after sunset is at Hanapepe’s open art galleries night. The food is fresh, local, and abundant, the beaches, open swaths of white sand and shimmering waters, inland is rocky and verdant, and shoes are not required. Here’s how to maximize your chill time on the garden island.
It’s not a proper trip to Kauai without shave ice. The Wishing Well Shave Ice truck in Hanalei has seemingly been around forever (in reality, since 1983). And it’s quite a sight: It’s old-school meets unintentionally kitschy meets the shave ice version of the Soup Nazi, and wild roosters peck the ground around the dusty truck. The owners are very testy (take too long to order or ask the wrong question and they’ll close the window for the day), on hot days they run out of ice before 3 p.m., and they tend to be closed more often than not. But if you can catch them at the right time (noon to 2 p.m. is your best bet), it’s all worth it. Most locals will vouch that has the softest ice on the island, and the syrup is thicker and richer than what topped your watery snow cone as a kid. Try the lychee or li hing mui (salted dried plum) with macadamia nut ice cream buried below the ice.
Duane’s Ono-Char Burger is a no-frills roadside stop on the mellow east shore, with an island-casual setting: order at the window of the bright red hut enshrouded in palm trees, then take a seat at a picnic table next to some regulars (shoes are notably optional). It’s the perfect fix after a long day in the water, serving up over two-dozen varieties of burgers and sandwiches. Try the “local boy:” a meaty charbroiled burger topped with pineapple and cheddar cheese, then slathered in teriyaki sauce (trust us).
Former notable San Francisco chef Jim Moffat (of 1990s 42 Degrees fame) now offers some of the best upscale dining on the island at his restaurant, Bar Acuda. He went on a surf trip to Kauai in 2003—then decided to never leave. Now he taps local farmers and fisherman for nearly all of his ingredients, compiling a menu that’s become a local favorite: think North Shore honeycomb with local goat cheese, and greens and slow-braised short ribs with date-and-almond salsa. Be sure to reserve a table in advance.
Carve out time for a pit stop in the town of Kalaheo for rum tasting at Koloa Rum Company, the only distillery on the island. And a notable one at that (it’s won a litany of international awards since opening in 2009). The rums are all high-quality single batch, using sugar grown in volcanic soil, and the tastings come with a very informative bartender who can tell you the story behind each variety. After, linger in the breeze on the picturesque porch overlooking a plantation.
About a dozen galleries line the main drag in Hanapepe, a micro-sized historic town on the south shore. From 6 to 9 p.m. on Fridays, Hanapepe’s Art Night is a good opportunity to meet local artists, gallerists, and musicians (and to snack on Hawaiian barbecue and tacos from truck vendors). Get to town early and explore the 19th century churches and architecture, which is surprisingly reminiscent of the old American West.
From Hawaiian Surfing Adventure’s outpost in Hanalei, you’re well-positioned for an array of water activity options. The launch point is on a lazy river, making it easy to take a kayak or stand up paddle board upstream through farms and mangroves, or left into Hanalei Bay. Surfers can rent boards here (and beginners can book lessons), or opt for a relaxing yet challenging yoga session.
If you’re near Hanalei, don’t miss the Saturday morning Farmer's Market from 9:30 a.m. to noon outside of the Hanalei Community Center. The market boasts mounds of local fruit and vegetables, fresh coconut drinks, juices, and crafts from local vendors. It gets packed, so arrive early.
The views from the St. Regis Princeville are unrivaled on the island (save for the views only accessed by trekking the Napali Coast). Still, don’t miss the epic postcard sunset on the sprawling veranda overlooking Hanalei Bay, as the sun patiently lowers behind the rugged Bali Hai formation. A lively Champagne sabering commences the evening. By day, access to the private beach is clutch: while the neighboring beaches are packed, here it’s mellow and has open access to a swath of reef that’s of the most colorful and sprawling on the entire island. Rent snorkel gear or a stand up paddle board right there, no lugging it across the sand required, and dive in. Then recoup at the pool and start all over again. Be sure to request an ocean view room; you won’t regret it.