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Many who visit Oahu think they can see, eat, and explore everything. It is an island after all. But while there may be just 597 square miles to cover (nothing compared to many other cities around the world) there really is an almost endless amount of activities to squeeze into a vacation here.

So when you’re ready to venture outside of the bubble of Waikiki and it’s conveniently located beaches, shopping and restaurants these are some of our favorite Oahu neighborhoods to explore:


Located on the windward (East) side of the island about thirty minutes outside of Honolulu, Kailua is a redolent beach town. Coming from Waikiki, the best way to get to Kailua is by taking the beautifully scenic Pali Highway.

If you’re looking to take a hike (and yes, we mean literally), one of the most popular, and fairly easy, hikes in this neck of the woods is the Lanikai Pillboxes hike, which boasts an incredible view of Kailua and Lanikai Beach. A few military bunkers remaining from World War II line the trail up to the top and serve as great resting points and lookouts. The best view from the Pillboxes is at sunrise, so for those who can get themselves out of bed while it’s still dark, you won’t regret it!

Kailua is a great spot not just for outdoor activities, but also for those who love to eat. Boots and Kimo’s Homestyle Kitchen is one of the most popular places to experience a traditional “local-style” breakfast with dishes like Portuguese sausage, local-style omelets, and their infamous Macadamia Nut Pancakes. Another breakfast/brunch option is Cinnamon’s Restaurant, known for their Portuguese Sweet Bread French Toast, Guava Chiffon Pancakes, and Red Velvet Pancakes on their menu. Be sure to arrive early to either restaurant to avoid the long lines!


Photo Credit: Salty Glass Co.

North Shore

While Honolulu is the metro hub of Oahu, always changing with new buildings and businesses each passing year, the North Shore prides itself on being the exact opposite with its unofficial slogan to “keep the country COUNTRY!” Largely untouched by development, the North Shore maintains its small city, old Hawaii charm, offering a taste of how island residents lived on Oahu decades ago.

If you do have time to venture out to the North Shore (the drive from Waikiki will take about an hour), make sure to stop by Giovanni’s Shrimp Truck for the most delicious garlic shrimp plate you will find this side of the Pacific. The food truck is covered in graffiti tags and Sharpie-scribbled messages by its patrons, with large red capital letters spelling “Giovanni’s.” With its simple menu (they offer just three different kinds of shrimp plates and one hot dog plate) and no frills appearance, Giovanni’s captures the down-to-earth spirit of the North Shore.

During the winter months, a trip to the Banzai Pipeline is well worth the drive. Massive waves break on this side of the island making Pipeline a very popular spot for pro surfers, and the host location for numerous surfing competitions such as the Pipemasters and Volcom Pipe Pro. This – along with other big-wave hotspots like Waimea Bay — are perfect to spread out and soak in some of the world’s best surfers conquering monstrous sets from the safety of the sand.

The Polynesian Cultural Center is also a great stop as you are making the trek up to the North Shore. Although you may want to dedicate the majority of an afternoon (or at least a few hours) here since it’s easy to get caught up in their wide assortment of activities and displays. Inside the PCC are several villages each representing the different people of Polynesia: Tonga, Tahiti, Marquesas, Hawaii, Fiji, Aotearoa, and Samoa. As you tour the property, each village shares their culture in a fun and interactive way; sometimes through a show, and other times by teaching a game.


Pearl City

While it’s definitely not a well-known area of town in travel maps, Pearl City is home to many great activities for visitors. For example, Pearl City is home to the Aloha Stadium Swap Meet, which takes place every Wednesday, Saturday, and Sunday, and features hundreds of vendors selling anything and everything from clothing and accessories to artwork and local snacks. You can spend a few hours wandering the rows, shopping for gifts for friends and family back home – as well as souvenirs for yourself.

If you visit Oahu, chances are you’ll want to dive into the island’s history with a visit to Pearl Harbor, the infamous site of a surprise military attack by the Japanese Navy against the United States nearly three quarters of a century ago. This historic site is the perfect space to learn more about World War II and experience the moving site in person.


The neighborhood of Kahala is a short fifteen-minute spin outside of Waikiki and a popular destination for shopping, eating, swimming and playing. Kahala Mall is a favorite for locals and tourists alike because of its many local boutiques like Fighting Eel and 33 Butterflies, as well as a popular Whole Foods Market store, which offers a great assortment of take-and-go options to enjoy back in your hotel room.

Even if you don’t choose to stay there, a visit to the Kahala Resort and Spa, a luxurious resort with stunning views of the ocean, is worth a quick trip. Enjoy a meal at any one of the hotel’s popular restaurants like Hoku’s, Arancino at The Kahala or Plumeria Beach House and then walk it off by paying a visit to the hotel’s stingray pools or waving hello to their friendly dolphins.

If you’re looking to work on your tan or get your feet wet, Cromwell’s Beach is a favorite among locals. There is always ample street parking, and plenty of space to sunbathe, swim or shape sandcastles. If you’re looking for a quick dip in the water or a quiet place to read your book on the beach, this is it!