Perfect Weekend in Oahu, Hawaii
Whether you land on Oahu for a layover en route to another far-flung destination or you’re island hopping across the Aloha State, our weekend guide will help you soak up as much Oahu magic as possible in two days.
Our itinerary hits the highlights of Hawaii's third largest island, and is perfect for first-time visitors, with stops at world-class beaches from south shore to north, must-try dishes and drinks (because mai tai, or it didn't happen), and glimpses of the island's rich history.
Day 1: Soak Up Waikiki
Vacation visions of Oahu are often dominated by Waikiki's arching sand beaches studded with palm trees, bordered by high-rise hotels, and punctuated by Diamond Head Crater.
Waikiki is a worthy place to while away a trip to Oahu (though it's just part one of your big weekend adventure), and since it's close to the airport, it's a natural homebase. Once your plane lands, grab your bags, pick up a rental car (you’ll need it for exploring tomorrow), and head into the heart of the south shore.
Stay Here: If it’s iconic Oahu you seek, you can’t miss it at the 528-room The Royal Hawaiian, a Luxury Collection Resort that was first opened in 1927 and still retains historic charm amid modern upgrades and luxuries.
More excellent lodging options include The Laylow, a recently-renovated mid-century gem, part of Marriott’s Autograph Collection, just two blocks from the sand and perched between much of the south shore’s best food spots; and Surfjack Hotel and Swim Club, a 1960s cabana meets cool Hawaiian getaway with a hype-worthy pool.
Sit by the Sea: If you stay at the Royal Hawaiian, you can pop up a spot under the resort’s pink umbrellas or bring your own towels and stake your claim on the bustling shore. Guests on the beach are welcome to bring their own beach gear, but Royal Hawaiian chairs are reserved for hotel guests.
Walk along the beach to Moana Surfrider, a Westin Resort & Spa, and stop at the Surfrider Cafe for healthy, light bites you can take to go. Pick from acai bowls, fruit, salads, and sandwiches, and nibble as you make your way back to your spot on the sand.
Catch the Waves: Once you’re fortified and have soaked in the turquoise water view from your towel, head over to Waikiki Beach Services for one-on-one surfing lessons, ride the waves in an outrigger canoe, or catch a ride on a catamaran with Na Hoku and Manu Kai in front of Moana Surfrider. You’ll be whisked out of Waikiki Bay and around Diamond Head crater, and the views on the return trip make for incredible photos.
Get Tiki'd: When cocktail hour hits, take the six-minute walk from The Royal Hawaiian to Hideout at The Laylow for one of Honolulu’s best mai tais. The Laylow’s spin combines pineapple and lilikoi juices to produce photo-worthy liquid layers that are topped with a pretty paper straw and orchid petal garnish.
Eat Local: After a mai tai (or two), walk three blocks to the Surfjack Hotel for dinner at Ed Kenney's Mahina & Sun's restaurant (reservations recommended). The decor pays homage to famous surfers; a wallpaper of shaka signs blankets the intimate dining room that sits just steps from the hotel’s courtyard pool (make sure you snap a photo of the bottom and its “Wish You Were Here” design). The menu runs deep with locally-sourced foods, from ahi tartare to pork ragu rigatoni.
Day 2: Diamond Head, Hawaiian History, and a Scenic Drive
Rise early, fight back your mai tai haze with some Hawaiian coffee (Honolulu Coffee has convenient locations in Waikiki), and prepare to steal away from the south shore for beautiful vistas, sweet surf, and some truly Hawaiian experiences. On the way out of town, choose between a scenic hike or a historic tour:
Hit the Trails: You saw it from the catamaran, now it’s time to meet Diamond Head, the towering volcanic crater, up close. The hike from trailhead to summit is less than a mile (1.6 for the round trip). Entrance fee is $5 per car. Hike early to avoid crowds—and the heat—and bring water and sunscreen.
Tour a Pacific Palace: Doris Duke’s Shangri La, originally a home built in 1937 for the tobacco heiress, is today an Islamic culture center that curates Duke’s worldly art collection. Tickets are $25 per person, and it’s only accessibly via a shuttle bus from the Honolulu Museum of Art; closed Sunday, Monday, and Tuesday.
Ride the Windward Side: The Windward Coast of Oahu (the east side of the island), only a 30-minute jaunt out of Honolulu, is a world away from the fast-paced Waikiki streets. It can be colder and rainier here, so pack accordingly. You may need to catch your breath as the tunnels you pass through open up to towering, verdant mountains and the ocean beyond. Follow the two-lane highway around the island, taking in the small towns, rolling rainforest-covered hills, and miles of beach. Pro Tip: For a turn-by-turn guide to hidden gems along your route, download the Shaka Guide for Oahu. The GPS-enabled tour sticks right with you through every turn and pit stop.
Stop for Shrimp: After your morning hike or museum tour, you’ll likely have worked up quite the appetite. As you near Oahu’s North Shore, look out for roadside shrimp trucks. Giovanni’s is perhaps the most famous, but all are unique and delicious. Grab a plate—you’ll need cash to pay—and pop down at the picnic tables with a can of lilikoi juice.
Experience North Shore Magic: After lunch, you’ve still got a world of beautiful sites to catch on Oahu’s North Shore. Just past the shrimp trucks, stop for a quick swim—or jump from the rocks—at Waimea Beach. Spot turtles coming in for the day on many beaches along Highway 83. See a fruit stand? Stop for a cool drink of fresh coconut water.
Haleiwa, a bohemian surf town on the North Shore, is a fun stop to stretch your legs. Watch surfers on Bonzai Pipeline, a world-famous surf spot with 40- and 50-foot swells in winter and early spring. In summer, the water is as calm as the Caribbean, and equally beautiful. Boutiques, restaurants, and surf shops dot the road through downtown Haleiwa.
For a special sweet, stop at Paalaa Kai Bakery in Waialua and pick up malasadas, Portuguese fried yeast doughnuts rolled in sugar and sometimes filled with flavorful creams and jellies.
Pull Over for Pineapple: The landscape will change dramatically as you cut through the center of the island on the H2 through Oahu’s Central Valley. You’ll cruise by working farms and the Dole Plantation. If you have time, stop for the “Pineapple Experience,” and don’t leave without a DoleWhip.
Eat Local: The Pig & the Lady—a buzzy Vietnamese menu with the precision of a Michelin-starred restaurant, minus the price (reservation recommended); Moku Kitchen—a smart concept that unites Oahu’s natural sources with international inspiration, with dishes like pork-pineapple pizza and fish tacos. The honey-lilikoi foam topper makes the Monkeypod Mai Tai a must.
Stay Up Late: If you’re not ready to turn in just yet when you return to your hotel, walk to RumFire inside the Sheraton Waikiki. The poolside bar serves up a plethora of tropical rum drinks. Club night is every Thursday, Friday, Saturday, and Sunday at 9:30 p.m. with special DJ appearances.
Day 3: Homage to Heroes and Pre-Flight Fare
Honor American Heroes: In your last hours on beautiful Oahu, take in one of the most moving experiences: Pearl Harbor. The memorial and visitors’ center is a 20-minute drive from your Waikiki stay, so go ahead and pack up, grab a bite to eat at the coffee bar, and check out of your hotel.
Tickets for the Arizona Memorial Tour can be reserved online or picked up the day of your visit on a first-come-first-served basis. Get there early to beat crowds and get the best shot at tickets for your group.
Eat Local: You won’t find a lot of food choices near Pearl Harbor proper—it’s in a very active industrial zone—and you don’t want to stray too far from the airport. You can head back toward town a bit and stop at Koko Head Cafe for brunch (walk-ins only). Favorites like Kimchi Bacon Cheddar Scones and Auntie Alohi Cakes are unlike anything you’ll find on the mainland.
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