All days in Hawaii are perfect days. But at nearly 600 square miles, Oahu is much bigger than you might expect, so it can suffer from the plagues of traffic and general congestion just like any other metropolitan area. To make the most of your time, try your best to rely on local wisdom. Let the trip happen organically but, most of all, take a few moments to enjoy the beauty of the Aloha spirit.
Thankfully, the March time change works in your favor on the front end of this trip, since traveling to Oahu from the mainland means you’ll most likely rise very early to make your flight. If you’re savvy enough to book a room at the Forbes Travel Guide Four-Star Halekulani, you’ll be welcomed with a view of the sunrise just beyond Diamond Head, Oahu’s dormant volcano crater. After checking in, walk down to the resort’s famed Four-Star restaurant, Orchids. Make sure to try a taste of the banana-macadamia nut pancakes, a favorite of staff and guests alike.
While there are other eating and shopping options within walking distance from Halekulani’s prime location in Waikiki — this is in addition to beautiful poolside views — the beach is shallow and hard to access directly from the resort. Hopefully, you’ve rented a car, that way you can experience as much of the island as possible. Oahu is known for its awesome waves and devoted surf culture, two things that are on display this time of year. But keep in mind that while all beaches in Hawaii are public, they are not all created equal. Some are rocky and rough, while others are calm and perfect for snorkeling.
No beach is more renowned than Waimea Bay, a park one hour north of Honolulu, where legendary Hawaiian surfer and lifeguard Eddie Aikau grew up riding waves that would terrify most. Before your trip, make sure to watch ESPN’s brilliant 30 for 30 episode Hawaiian: The Legend of Eddie Aikau, a documentary that not only describes the state’s controversial history with U.S. imperialism, but also tells this icon’s legendary story. Every year, the Quiksilver In Memory of Eddie Aikau invitational performs opening ceremonies in Waimea Bay, only to complete the surfing competition if waves grow to an Aikau-worthy swell. The contest has run just eight times in its 30-year history. On a calm day (event or no event), Waimea Bay offers turquoise waters and thick, dark Oahu sand to dig your toes, attracting a diverse crowd of locals, tourists and international surfers.
For lunch, drive south to Haleiwa (Hah-lee-ay-vuh) Town, and stop in at Kono’s for the famous 15-hour kalua pork or our favorite, the Haleiwa Bomber, a breakfast burrito served all day and made with kalua pork, eggs, potatoes and cheese. If you’re in the mood for something sweet, nothing is more Hawaiian than a cup of shave ice. (Yep, “shave,” not “shaved” — the distinction is important.) Though the line is long at the historic Matsumoto’s, we found better flavors and more durable cups at a hole-in-the- wall shave ice joint called Anahulu’s located next door to Tropical Rush, a Volcom surf shop with some of the best swimsuits, souvenirs and apparel on the island. Make a purchase and receive a free shave ice as a perk — just make sure to order it with ice cream on the bottom. All that delicious sugary juice has to go somewhere, right?
Enjoy an afternoon either lounging at Haleiwa Ali’i Beach Park, or rent a kayak or stand-up paddleboard from Surf N Sea, and explore the river channel that bisects Haleiwa under the Rainbow Bridge.
Return to Honolulu before sunset to enjoy the nightly luau and live music at Halekulani’s famed House Without a Key. A favorite of locals and guests, the resort invites former Miss Hawaii pageant winners and local musicians to wow the crowd with traditional dance and song. Order a light appetizer of ahi sashimi or a fresh fruit plate to accompany a signature Mai Tai or a classic mojito. It’s a perfect way to wind down the night.
After an eventful first 24 hours, take it easy the next morning. Owned an operated by the Japanese hospitality group, Mitsui Fudosan, Halekulani offers the best of feng shui design and personal service, ensuring a relaxing stay. Beyond that, the staff will remember your name, they’ll recall where you’re from and keep a tab of what you like to drink. The cook may not know exactly how you like your Belgian waffles initially, but with a daily breakfast spread that includes griddle treats, fresh fruit, eggs and Hawaiian staples like Portuguese sausage, steamed rice and frittata, you’re still in for a grand experience. After eating, head to the pool; it’s serene in the morning, with a quiet, adults-only feel that’s only interrupted by the occasional crash of surf at the shoreline.
When you’re ready, hop in the car and drive a few minutes northwest to Chinatown, where another facet of Oahu’s history and dimension comes to life. This is where you’ll stroll the Oahu Market to check out traditional produce and a host of other exotic fruits and vegetables; the stalls are lined up next to duck, chicken and pork vendors. After you’ve explored the aisles of food and art, find your way to chef Andrew Le’s James Beard-nominated The Pig & The Lady, a stylish restaurant displaying Le’s fresh take on bánh-mi, pho and other Vietnamese fare. If there’s anything else you must try on the menu, it’s the papaya Pok Pok salad served with roasted kabocha and seeds, fried shallots, aromatic herbs and fish sauce. Make reservations in advance for this popular spot.
After lunch, take your pick of another beach experience. The beautiful 35-minute drive north on Highway 61 will take you to Kailua, a gorgeous (albeit a tad windy) beach town with a shoreline perfect for long walks. Take the time to stop at Nu’uanu Pali Lookout, a well-marked vista overlooking the eastern shore. If snorkeling is more your jam, Hanauma Bay is famous for a reason. But if you’re looking for lounging in the sun, boogie boarding or swimming, go no further than Waimanalo Bay.
Your trip to Oahu wouldn’t be complete without stopping at new local culinary favorite Town. There have been whispers that chef Ed Kenney recently entertained travel connoisseur Anthony Bourdain. If that’s not reason enough to make a reservation, the constantly changing menu is always full of sharable delicacies such as ahi tartare served with risotto cake and balsamic vinegar, pork chops or fresh catch like mahi-mahi served with veggies picked from nearby farms. “Local first, organic whenever possible, with Aloha always” is not just an applicable motto for Town; after 48 hours on the island, you’ll find the words to be quite fitting for Oahu as a whole.