O‘ahu is so stunning that the ali‘i, the kings of Hawai‘i, made it the capital of the island nation. Below, we presume that you'll be staying in Honolulu, which makes a good base for the rest of the island. Plus, it has the best dining options and a cosmopolitan liveliness unavailable anywhere else in the islands. If you prefer quieter nights, though, opt for a vacation rental in Kailua or on the North Shore and factor into the following itinerary extra time for traveling.
Day 1: Arrive & Hit Waikīkī Beach
Unwind from your plane ride with a little sun and sand. Take a dip in the ocean at the most famous beach in the world: Waikīkī Beach. Catch the sunset with a mai tai, Hawaiian music, and some of the loveliest hula you’ll ever see at House Without a Key.
Day 2: Surf in Waikīkī & Visit Pearl Harbor
Thanks to jet lag, you’ll be up early; take advantage with an early-morning surf session, aka dawn patrol, when the waves are smooth and glassy. Waikīkī has great waves for learning, and a surf lesson will have you riding the waves in no time. The poke (seasoned, raw fish) at Ono Seafood makes a great post-surf meal. In the afternoon, head to the USS Arizona Memorial at Pearl Harbor, site of the infamous 1941 attack. For dinner, go local and dine at Highway Inn for kālua pig, laulau, pipikaula, and poi.
Day 3: Explore the North Shore
Grab a fried malasada (hole-less doughnut) dipped in sugar at Leonard’s Bakery before heading to the North Shore. Stop in the quaint town of Hale‘iwa for a pineapple-lilikoi-mango treat at Matsumoto Shave Ice, and grab a picnic lunch from Beet Box Café. Pick one of the gorgeous North Shore beaches for a day of swimming and sunbathing. Waimea Beach Park is a favorite, no matter the season. In winter, if the waves are pumping and conditions are right, head to Pipeline and watch pro surfers ride this tube-like wave over razor-sharp reef. Heading back south, hit the shrimp trucks at Kahuku. Still daylight? Take the longer coastal road back into Honolulu.
Day 4: Snorkel in Hanauma Bay & Hike the Makapu‘u Lighthouse Trail
Get up early and grab some freshly baked morning pastries or a local-style breakfast at Diamond Head Market & Grill before heading to Hanauma Bay for snorkeling. If you’re a strong swimmer and the water is calm (check with the lifeguard), head out past the reef and away from the crowds, where the water’s clearer and you’ll see more fish and the occasional turtle. Continue beach-hopping down the coastline—watch bodysurfing daredevils at Sandy Beach. Hike the easy Makapu‘u Lighthouse trail, with views to Moloka‘i and Lāna‘i on a clear day. In winter, you may even see migrating humpback whales. Take the Pali Highway home to Honolulu—and be sure to stop at the Nu‘uanu Pali Lookout. For a night out, head to Chinatown, where a slew of new restaurants have opened: Start with a cocktail in the courtyard at Tchin Tchin and move on to dinner at Senia.
Day 5: Glimpse Historic Honolulu & Experience Hawaiian Culture
Fuel up at Koko Head Café, an island-style brunch spot before heading to downtown Honolulu to see the city’s historic sites, including the ‘Iolani Palace. Lunch at The Pig and the Lady for modern Vietnamese food, pick up some tropical fruit at one of the many Chinatown vendors, and browse the new boutiques started by Hawai‘i’s young creatives. Spend the afternoon at the Bishop Museum to immerse yourself in Hawaiian culture, then head up to Pu‘u ‘Ualaka‘a State Park to watch the sunset over Honolulu. For dinner, get a taste of Honolulu’s spectacular Japanese cuisine at Sushi Izakaya Gaku.
Day 6: Relax at Kailua Beach
On your last full day on O‘ahu, travel over the Pali Highway to the windward side of the island. Dig into a stack of liliko‘i (passion fruit) pancakes at Moke’s Bread and Breakfast and then spend the rest of the day at Kailua Beach. It's the perfect beach to kayak or stand-up paddle to the Mokulua Islands (or, as the locals call it, “the Mokes”) or simply relax. For your last dinner, splurge at Alan Wong’s Restaurant, with classic local-style foods reimagined for the fine-dining table.
Day 7: Marvel at Shangri La
Head to the Honolulu Museum of Art for your tour of Shangri La, the private palace of tobacco heiress Doris Duke. Filled with Islamic art, the interior is stunning, but so is the location, on a cliff facing Diamond Head. Then, take one last look at Diamond Head and Waikīkī... from the ocean, aboard the Holokai Catamaran.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.
