9 of the Best Towns on Oahu and How To Visit

The now-quintessential surf town of Haleiwa, which started life as a 19th-century sugar plantation town, retains its pastel-hued historic buildings and vintage bungalows. However, these days they’re filled with plentiful boutiques and eateries to explore, including the ever-popular Matsumoto Shave Ice that has been serving up the chilled treat since 1951.

And located right before Haleiwa is an Oahu must-do: the Dole Plantation. Dating back to 1901, the Dole Plantation has morphed into a family-friendly attraction centering around all things pineapple. Get lost in the massive pineapple-shaped hedge maze, ride aboard the Pineapple Express Train, and then cool off with a cup of the famously tarty Dole whip. Or make a whole day out of it on a guided tour of the town and plantation.

If you’re considering whether to stay in Waikiki vs. the North Shore on Oahu, keep in mind that the choice of venturing north offers a slower pace and less development—and few places encapsulate this no-worries lifestyle quite like Laie.

This Oahu town feels remote and undeveloped, making it ideal for those hoping to unplug from the daily grind. Having said that, it is home to the Polynesian Cultural Center, one of the most popular attractions on Oahu, where you can learn about various Pacific cultures at immersive villages. While you're in the area, book a 3-day pass to the cultural center, and upgrade your admission to include a luau and the dramatic HA: Breath of Life show.

If you’re taking the scenic drive from Honolulu to Oahu’s windward side, you can choose between two options: the Pali Highway that winds through the verdant Koʻolau Mountains or the rugged coastline from Hawaii Kai to Waimanalo. Either way, your final destination should be the quaint beachside community of Kailua.

Here, the pace is slow and relaxed. People ride their bikes around town, hitting the coffee shops and brunch spots before going to the beach, where the white sand is so soft and fine, it’ll stay with you until the next day. An area favorite is the postcard-perfect, chill Kailua Beach Park, though those seeking a more active visit can join a kayak and snorkel tour to the nearby offshore Popoia Island instead.

A single main road runs through Waimanalo, a town on Oahu flanked by the turquoise ocean on one side and the lush Koʻolau Mountains on the other. With a backdrop like this, it’s no wonder why the Waimanalo lifestyle is all about appreciating nature with a laidback attitude.

Take a cue from the local families who spend all day enjoying the fine, sugary sands of Waimanalo Beach Park by making this the locale of your next beach outing—or at least get a glimpse during a Circle Island tour of Oahu.

Insider tip: Don’t forget to pack snacks and a boogie board to play with in the small shore break.

Kaneohe is an ideal jumping-off point for exploring the verdant Koʻolau Mountains that draw abundant rainfall, causing waterfalls to flow down their jagged peaks. Drive through the Hoomaluhia Botanical Gardens and stop at any picnic area or hiking trail that catches your eye—the views of the Koʻolaus are always astounding.

If you’re itching to enjoy the ocean, you’ll also find the calm, protected waters of Kaneohe Bay—or K-Bay, as locals call it—right around the corner. The picturesque saltwater sandbar, which is the largest in the world, was once the site of a royal fishpond and agricultural hub, but now exists as a popular spot for snorkeling or from which to embark on an Oahu kayaking tour.

By now, Oahu’s North Shore has captured the hearts of many travelers, and of the towns in the area, Waialua stands out for its quieter, more undeveloped coastline. Cast to the left of the livelier Haleiwa, this tight-knit community is known for its deep roots as a sugar plantation town. Before that, it sat at the crossroads of ancient Native Hawaiian pathways as a fertile agricultural hub.

Now, Waialua’s sprawling Mokuleia Beach Park—which translates to “Isle of Abundance” in Hawaiian—is the town’s crown jewel, but local businesses such as Waialua Estate Coffee and Chocolate are worth a visit too.

It doesn’t take long to realize the Oahu town of Kapolei looks a bit different from the rest of the island. In another life, this sunny, dry region belonged to sugar and pineapple plantations, but all of that changed when the Ko Olina resort area opened in the 1990s, bringing a newfound energy.

As one of the fastest developing areas of the island, Kapolei has earned itself the nickname of “Second City” for its buzzing atmosphere that closely follows Honolulu. Its residential neighborhoods seem bright and airy, located adjacent to shopping centers teeming with businesses, such as DB Grill, a local outpost serving up Asian fusion.

Gorgeous bays, rugged mountain peaks, and uncrowded beaches comprise the quiet community of Kaaawa, situated on the northeastern shores of Oahu. Start with a morning hike at Crouching Lion, a short yet challenging trail up a steep ridge, before dipping into the gentle waters at Ahupua'a O Kahana State Park, which transforms into a gliding longboard surfing wave when the conditions align.

The culturally significant Kualoa Ranch can also be found here. Best known as a filming location for more than 200 movies—including the Jurassic Park series—Kualoa Ranch is like a theme park but set across undeveloped acres of natural beauty. Here, join a horseback riding tour, see Hollywood movie filming sites, or enjoy an experience that involves restoring ancient taro fields.

Related: Know Before You Go: Visiting Kualoa Ranch

While planning where to go on Oahu, not all travelers think to venture to the west side, one of the last few parts of the island that still feels intrinsically local. However, this area brims with a rich history, given that it was a former ancient fishing settlement and is home to a famous surf break. (In Hawaiian, Makaha means “fierce”—fitting for its big wave reputation.)

However, there’s more than just surfing in Makaha. You can also check out Oahu hiking trails that traverse the rocky Kaʻena Point nature preserve where endangered monk seals bask in the sun.

Related: 9 of the Best Hiking Trails on Oahu