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You could head to Diamond Head Monument and get stuck on the climb up in a gaggle of infuriatingly unequipped lookyloos, or literally take the road less travelled for a more unique experience. Bike Hawaii hosts Bike and Hike treks on its own private trails, which means you’ll have the path—and the gorgeous waterfall at the end—all to yourself, and the views as you speed down the winding mountain road on a vintage cruiser will be unencumbered.

A guided tour of Shangri La, heiress Doris Duke’s former private residence, is a trip back to the gilded age of Hawaii, when the journey was made via steamer ship and luxury reigned supreme. Arrange a tour of the oceanfront palace through the Honolulu Museum of Art.

If you’re on the pristine North Shore of the island, a surf lesson is a must—otherwise, it’s like going to the Vatican and skipping the Sistine Chapel. There’s an on-site outpost of the famed Hans Hedemann surf school, which will take you to one of the nearby coves to see if you have what it takes to hang ten. Ask (OK, insist) on Rocky Canon, former pro-surfer-turned-wave-whisperer, to be your spirit guide—if the sight of his effortless cool on a board doesn’t spur you on to take up the sport, then you’re a lost cause, grommet.

Eat

Lucky Belly has been the table to score for the past year (they oddly only accept reservations until 6:30 p.m., then it’s all walk-in), but it’s worth the hassle—elevated ramen, lobster shu mai and duck tataki are the types of items that will demand an Instagram post or two. The wine list is limited, but corkage is only $15 and it’s free if your wine is more than five years old.

New York native chef Lee Anne Wong—the former Top Chef contestant with a resumé that includes stints working with Jean-Georges Vongerichten and Marcus Samuelsson—almost single-handedly brought tourists to the residential Kaimuki neighbourhood with Koko Head Cafe, which serves, hands down, the best breakfast on Oahu. Kimchi cheddar bacon scones followed by a miso smoked pork and green onion omelette followed by a nap on the beach.

For the past five years, Marukame Udon has been the people’s choice for Honolulu udon, helped by its proximity to Waikiki and its rock-bottom prices (spending more than $6 is a trick). The bitter truth is…it’s totally worth it. Its freshly hand-pulled noodles merit the permanent lineups, so if time is tight you have two options: go for a ramen breakfast (which is a revelation) or head downtown to the new location on Fort Street.

Take Out: Poke

Tamura’s Fine Wine

As a rule, we don’t condone buying raw fish from a liquor store, but Tamura’s Fine Wine has the best selection of wine between Seattle and Tokyo and its poke is the freshest possible, so put a chilled bottle of Alsatian riesling under your arm, order up some sashimi-grade ono with sesame and shoyu and you’re set.

Shop

Roberta Oaks

Busloads of tourists descend upon Waikiki for its designer stores, but if your tastes veer towards the more eclectic, then visit the up-and-coming Chinatown neighbourhood, where you’ll find non-cliché items like the local hipster hats and shirts at in4mation or the classic Hawaiian shirt reinterpreted at Roberta Oaks.

Stay

Tucked away in the priciest residential neighbourhood in town, the Kahala seems like a mirage when you come upon it. You’re driving along Kahala Avenue, gawking at the houses that start at $13,000,000 (for an empty lot) and buzz $50,000,000 at the top end, and suddenly a hotel appears. It was the most expensive hotel ever built when it debuted in 1964, and the low-key approach to luxury and the distance from Waikiki have made this the choice of discreet bold names ever since.

Or, there’s the Modern Honolulu. Take a deep breath as you step into the clean white lobby: the broken surfboard 3D collage jutting out of the wall behind the registration desk delights the eye, and the heavenly custom plumeria scent is an olfactory reminder that you’re now officially on vacation. The Modern eschews the Hawaii Five-0 shtick in favour of hip simplicity: an urban boutique hotel with an ocean view.