The 6 Best Oahu Hikes

Photo of the Pillbox, one of the best Oahu hikes.Hawaii boasts one of the most biodiverse ecosystems on the planet, and the island of Oahu is no exception. Hidden at the heart of Oahu, several miles from Honolulu’s skyscrapers, Waikiki’s pristine sand, and the North Shore’s tall waves, thrillseekers and adventurers alike can quickly discover an array of breathtaking hiking trails that meander through this glorious, undisturbed land. There are nearly a dozen ways to explore the island, including via horseback, mountain bike, and ATV. However, a good, old-fashioned hike remains the most popular channel for an exploratory adventure. Prince Waikiki’s worldly concierge team has sagely pieced together this handy list of the six prettiest Oahu hikes that range from a steep climb up a volcanic tuff to a jaw-dropping journey along a sweeping oceanic ridge.

The Top 6 Oahu Hikes: A Trail for Every Traveler

Most mountainous Oahu hikes do require quite a bit of smile-inducing physical exertion, as the island is freckled with towering peaks. It’s important to plan in advance in order to fully relish the experience. Remember to bring the essentials, such as hiking boots, bottled water, a virtual map, and, perhaps, a backpack filled with a mid-day picnic. Without further ado, here are six classic hikes near Waikiki.

Lanikai Pillbox

Lanikai Pillbox, also known as Kaiwa Ridge, boasts the island’s prettiest Pacific Ocean viewpoints. Thus, this 1.8-mile trail does welcome a slew of travelers and locals alike on a daily basis. That being said, the Pillbox is one of the most quintessential Oahu hikes, and it’s only a 30-minute drive from Prince Waikiki.

Diamond Head

But, of course, a long-awaited escape to the sunny, picturesque isle of Oahu wouldn’t be complete without a gradual climb to Diamond Head’s peak. Travelers often combine a trek up Diamond Head with a stop at Shangri La, a picnic, an authentic luau, or some snorkeling on Queen’s Beach.

Makapu’u Point Lighthouse

The island of Oahu is home to only six lighthouses. None of them can match the natural beauty that surrounds Makapu’u Point Lighthouse, a stout, 46-foot-tall beacon with a vibrant red cap. This reasonably easy 2.5-mile trail remains one of the premier kid-friendly hikes on Oahu.

Crouching Lion

Speaking of kid-friendly: Crouching Lion is an ultra-brief, 1,000-foot climb along the North Shore. While the trail is very steep, it’s so short that most families can embark on the journey together. The views obtained from the summit of Huilua Pond, Kaaawa, and Ahupuaʻa ʻO Kahana State Park are genuinely heartwarming.

Photo of Olomana Trail, one of the best Oahu hikes.Olomana Trail

Without a doubt, the most difficult of these six Oahu hikes is the treacherous, 4.4-mile journey along Olomana Trail. It’s recommended for seasoned hikers only, as travelers must endure nearly 2,000 feet of elevation gain on the trail. Naturally, the head-turning views of the “Three Peaks” are well worth the sweat needed to finish the trek.

Koko Crater

Koko Crater remains the top-rated hike on the island, according to AllTrails.com. It’s steep, windy, and undeniably gorgeous, as hikers eventually gain a bird’s-eye view of the island’s southern reach. There are hundreds of steps involved, so it’s best to arrive with a “full tank of gas.”

Best Hotels in Honolulu, Hawaii

The perfect place to start and finish an idyllic day on the beautiful island of Oahu is inside harbor-front Prince Waikiki, the top-rated hotel in Honolulu, according to TripAdvisor. Prince is widely celebrated for its sunset dining, sparkling infinity pool, live music, and VIP Club Lounge. The hotel is also a short walk (or Biki ride) from prime surf, street art, craft breweries, and sleek cafes. Please dial 1-855-622-7558 to book a well-deserved getaway to award-winning Prince Waikiki.