Head to Hawaii for Just a Long Weekend? Yes, We Can!

Chase the sun in Kailua, President Obama’s low-key hideaway.

By Julia Silverman December 31, 2019 Published in the January 2020 issue of Portland Monthly

The sun-starved hordes of Oregonians hopping on an Alaska or Hawaiian Airlines direct flight to Oahu this time of year often head, lemming-like, for Waikiki Beach, home of an ABC convenience store on every block, sprawling hotels, and a thin golden strand of sand packed with the best people watching this side of Venice Beach.

There is an alternative: Drive half an hour northeast from Honolulu’s airport, through the jagged green of the Ko’olau mountains, and end up in Kailua, the small, laid-back town that’s been Barack Obama’s December-break happy place for years.

Image: Courtesy Goen

There are no hotels—just a few modest bed-and-breakfasts—but plenty of vacation rentals available (though this being Hawaii, nothing comes cheap). Still, having a rental with a kitchen lets you take advantage of the super fresh fish and local produce on offer during the Thursday-night Kailua Farmers Market, in the Longs Drugs parking lot just behind the town’s main drag. Wait in line at the Pig and the Lady’s booth for their spicy bún bò huê and finish off with a passion fruit–flavored treat from Ono Pops for dessert.

Work it off the next morning at Kailua’s true claim to fame, its 2.5-mile, crescent-shaped stretch of white-sand beach, with waves that are consistently just right for boogie-boarding and bodysurfing. Pro tip: Find the Kalama Beach entrance at 248 N Kalaheo Ave, rather than the busier, tour-bus-clogged southern entry point at Kailua Beach.

Splash around or rent a kayak from Kailua Beach Adventures, just across the street from the beach, and make for the unpoetically if accurately named Flat Island, about a quarter-mile from shore. Step carefully when you arrive—nesting seabirds have the right of way. Or, get up early to beat the crowds at the Lanikai Pillbox hike, a quick, steep one-miler to a dizzyingly sumptuous lookout.

Reward yourself with a reservation for the outside seating area at Hawaii superstar chef’s Roy Yamaguchi’s latest restaurant, Goen Dining & Bar, opened in late 2018. (Order the fettuccini with dashi cream, pickled ’shrooms, and crispy kale.) And don’t leave town without a souvenir. The cool kids all like Mu’umu’u Heaven, which takes discarded aloha shirts and muumuus and upcycles ’em into on-trend halter dresses, jumpsuits, and other goodies.

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