Oahu has a little bit of everything. It’s where you and your besties can find great shopping, exotic foods, rich culture and stellar surf, all in one place. It makes sense Oahu’s nickname is the Gathering Place.
Here’s the itinerary for two perfect days on Oahu. Fair warning: You will want to stay longer.
Day 1: Waikiki
Being on vacation means eating well, and a visit to Oahu won’t disappoint. Whether it’s your first time to the island, or your fifteenth, no trip is complete without a visit to Leonard’s Bakery for malasadas. These Portuguese pastries are baseball-sized balls of delicious deep-fried dough dusted with sugar. Leonard Rego opened his namesake bakery in 1952. Today, Leonard’s is synonymous with malasadas. In addition to its addicting sugary pastries, the bakery also sells pies, cookies, cakes, bread and more. The most popular items are still the original malasadas and the custard cream-filled variety. Grab an iconic pink box filled with malasadas to share. It’s hard to eat just one.
After you’ve all had your fill of malasadas, continue down Kapahulu Avenue into Waikiki. The busy avenue eventually leads to Kalakaua Avenue, renowned for its long stretch of beach and sophisticated resorts. At the Diamond Head end of Kalakaua Avenue, a nine-foot bronze sculpture greets hundreds of visitors to Waikiki each day. It’s the Duke Kahanamoku statue. Born in 1890, the congenial Native Hawaiian grew up in the surf and sand of Waikiki. He went on to become an Olympic athlete, a Hollywood star, Hawaii’s ambassador of aloha and the father of modern surfing. Located on Kuhio Beach, the Duke statue, as it’s affectionately known, is not only a great Instagram photo opp, but also a recognizable Waikiki meet-up spot before hitting the beach or grabbing lunch.
Just a four-minute walk up Kalakaua Avenue from the Duke statue is the International Market Place. With more than 70 stores, including Saks Fifth Avenue, Maui Divers Jewelry, Vera Bradley, Trina Turk and more, this a great spot for some group retail therapy. This Waikiki institution was first built in the late 1950s and included a tree house atop a banyon tree, tiki nightclub and kiosk vendors. In 2013, the market place closed and three years later a revamped three-story shopping center debuted. Don’t worry, the market place’s more than 160-year-old banyan tree remains. When you’ve worked up an appetite, head upstairs to eat at restaurants such as Hawaii chef Roy Yamaguchi’s Eating House 1849, seafood restaurant Herringbone, or steakhouse Stripsteak. Even better, there are shaded areas on each level and serene sitting areas surrounded by water features.
When you’re ready to jump into Waikiki’s tranquil blue waves, look no further than the Duke Kahanamoku Lagoon, at the Hilton Hawaiian Village Waikiki Village Beach Resort. Fronting the hotel, the five-acre lagoon is more than just a seawater lake in Waikiki. Named in honor of the surfing legend, it’s a water lover’s dream for you and your friends. Here you can standup paddle, kayak, aqua cycle and swim. The sandy beach is the perfect place to relax when you need a breather.
If you’re visiting the Hilton on a Friday, stick around past sunset. (It won’t take too much convincing; the resort has 20 restaurants and bars.) For more than 25 years, the Hilton Hawaiian Village has put on a weekly Friday night fireworks show. It’s become a Waikiki tradition of sorts, with visitors and locals lining up on the beach in anticipation of the technicolor pyrotechnics. From May through August the Friday fireworks show begins at 8 p.m. and from September through April, the show starts at 7:45 p.m. If you want to watch some dancing with your fireworks show, get tickets for the Rockin’ Hawaiian Rainbow Revue ($30). It’s a contemporary hula show 45 minutes before the fireworks display.
For a blissful ending to an action-packed day, head to Rumfire in the Sheraton Waikiki. This ocean front bar has happy hour daily from 3 to 5 p.m. as well as live music every evening starting at 5 p.m. As the name implies, this bar is known for its rum cocktails, such as the Cucumber Lavender Mojito, or the Sand and Sea, made with organic rum, passion fruit puree, pineapple juice, sweet & sour and a drizzle of DeKuyper blue curacao. Tasty pupu (appetizers) include char broiled mahi mahi tacos and the miso butter fish with sautéed corn. On Fridays and Saturdays, it’s a hopping club scene.
Day 2: North Shore
Your first day on Oahu was all about the energy of Waikiki. To experience the laid-back vibes of the island, simply head north. There you’ll find tranquil towns, local boutiques and a smattering of food trucks in between world-renowned beach parks.
Upon entering Haleiwa, you’ll be greeted with a charming sign. A surfer and his wave pierce the words Haleiwa, North Shore, as a yellow arrow above points the way to everything you need for your day of fun: “food, gas, shops, beaches.” You’re officially entering Oahu’s bucolic North Shore. (There are actually two signs — one at each entrance to Haleiwa.) The sign is the island’s version of the Welcome to Fabulous Las Vegas sign. So go ahead, pull over, get out of your car and take a selfie with your friends. There’s no judgment.
After you’ve Instagrammed your Haleiwa sign selfie, make your way to Matsumoto Shave Ice. Now a shave ice joint, Matsumoto first opened in 1951 as a general store. Today, it’s the most popular place to get shave ice in Hawaii. On a busy day, the store sells more than 1,000 shave ice cones! Choose up to three flavors for your cone, and add extra goodies such as ice cream, condensed milk, mochi and adzuki beans. With nearly 40 flavors — from strawberry and pineapple to white cake and green tea—the combinations are endless.
Even if you’re not quite hungry after the shave ice, just one whiff of wafting garlic from Giovanni’s Shrimp Truck will spontaneously make you hungry again. Plus, it’s almost required to stop for a shrimp plate lunch when you’re on the North Shore. The area is renowned for its freshwater aquaculture farms. Giovanni’s is one of the originals, first operating out of a converted bread truck in 1993. The shrimp scampi is Giovanni’s mainstay menu item. Each plate comes with a dozen shrimp, ready for you to peel and eat, and two scoops of rice, all generously drizzled with garlic lemon butter.
After lunch, meander over to one of the North Shore’s pristine beaches. In the summer, they’re perfect for swimming, surfing and snorkeling. During the winter, Mother Nature shows off with 10-plus-foot waves, attracting the world’s best surfers during annual contests. So, during those months, it’s best to observe from a safe distance.
In just two days, you and your friends have seen the best of Oahu, from the bustling city to the charming country. Oahu really does have a little of everything.
Where to Find These Places
933 Kapahulu Avenue, 808-737-5591, LeonardsHawaii.com
Duke Kahanamoku Statue
Kuhio Beach Park at Uluniu Avenue
2330 Kalakaua Avenue, 808-931-6105, ShopInternationalMarketplace.com
Parking, with validation: First hour is free; afterward is $2 an hour.
Hilton Hawaiian Village Waikiki Village Beach Resort
2005 Kalia Road, 808-949-4321, HiltonHawaiianVillage.com
Located in the Sheraton Waikiki: 2255 Kalakaua Avenue, 808-922-4422, RumfireWaikiki.com
62-330 Kamehameha Hwy, Haleiwa, HI 96712
62-400 Joseph P. Leong Hwy, Haleiwa, HI 96712
Matsumoto Shave Ice
66-111 Kamehameha Highway Suite, Suite 605, 808-637-4827, MatsumotoShaveIce.com
Giovanni’s Shrimp Truck
56-505 Kamehameha Highway in Kahuku; 66-472 Kamehameha Highway in Haleiwa, GiovannisShrimpTruck.com