Sunrise over the Pacific Ocean from pillbox #2 along the Ka’iwa Ridge Trail (Lanikai Pillbox Hike)

My first – and so far only – trip to Hawaii took us to O’ahu. The catalyst for the trip was to run an Xterra half-marathon trail race, but the trip was so much more! I’ve heard that each of the Hawaiian islands has its own personality. What I loved about O’ahu is that it offered so much variety.

We experienced Hawaii’s beautiful beaches, snorkeling in its turquoise waters, inspired sunrises, waterfalls, history and island culture. In this article, wander with us around the island as we take you on some of our favorite hikes, tours and beach days.

Of course, one of the first decisions when starting to plan your trip is where to stay. There are many beautiful hotels and resorts on O’ahu, especially if you choose to stay in or near Honolulu. But if you want something different, consider staying at a VRBO. We found one on the eastern (windward) side of O’ahu, in a house up on a hill, and the benefits were amazing! We had a full kitchen and a lanai (patio) with a view of Koko Head and a barbecue. Keep reading to learn more about how that shaped our experience.

Hikes on O’ahu

In the week we spent on O’ahu we did three spectacular hikes - not including our hike/run through Kualoa Ranch (keep reading for more on that experience). All three were listed on Hawai’i Guide’s list of "Best Places to Hike on Oahu” and all three were amazing!

Our hikes ranged from an easy, albeit muddy (we were there in the rainy season), hike to Manoa Falls, to the strenuous, adventurous climb up Koko Head that offered stunning views from O’ahu’s eastern side.

Disclaimer: This post contains affiliate links for products and/or services we love. If you decide to make a verified purchase through the links in this post, I will earn a small commission (at no extra cost to you). Thank you for choosing to wander with us. We hope your adventures are filled with as much joy and awe as we’ve experienced!

Koko Head Stairs

Our first hike was definitely the most challenging, but what an adventure! The Koko Crater Arch Trail (also known as the Koko Head Stairs) was an advanced hike to the top of Koko Head. It was only about a mile-and-a-half round trip, but took nearly three hours. To reach the summit, there are more than 1,000 railroad ties to climb straight up the mountain. The railroad path is leftover from World War II when the trail was used to transport supplies. Today, the hike leads to panoramic views that are well worth the effort.

Ka’iwa Ridge Trail / Lanikai Pillbox Hike

This was probably my favorite hike. Like Koko Head, the trail has a historic context rooted back to World War II when the concrete structures (“pillboxes”) were used as lookout stations. Today, they are covered in colorful graffiti that give the area a feeling of nostalgia that changes with each new tag left by visitors.

We started hiking in the dark (definitely bring your headlamp or a flashlight) and made it to the summit just in time to sit and watch the sunrise over the Pacific Ocean. Sitting atop the pillbox at dawn provided a spiritual space to reflect before continuing further along the trail.

Manoa Falls Trail

This was a gentle hike, just over a mile and a half roundtrip. The 150-foot Manoa Falls was beautiful and could be the perfect ending to an afternoon walk through the rainforest. But, we’d heard about an old banyan tree - some say it’s haunted - and wanted to check it out. To get there, we followed a trail leading off the main Manoa Falls Trail, this one more difficult as we navigated all the roots and muddy patches. But, the reward of witnessing the giant tree with its stringy above-ground roots draping from its branches to the earth, was a site to behold.

Beaches

Exploring the beaches of O’ahu is a perfectly Hawaiian thing to do. Some are rocky, others are soft, sandy expanses. Some have quiet waters perfect for swimming or snorkeling, others are renowned for big waves and brave surfers.

☞ Tip: Before heading out to swim, snorkel or surf, be sure to check weather and water conditions. Ocean and beach conditions vary greatly around the island and with the seasons.

Waimea Bay Beach Park

Located on O’ahu’s north shore, Waimea Bay is one of the places to go to watch the surfers. During the winter months, waves at Waimea Bay can reach up to 40 feet, making it a prime (and challenging) spot for expert surfers. During the summer months, the water tends to be gentler and a great spot for swimming and snorkeling. When visiting, pay attention to weather alerts and posted surf flags indicating water conditions. The beach park features picnic tables, restrooms and showers; as well as parking. Across the street is the beautiful Waimea Botanical Garden.

Makapu’u Beach Park

Located on the southeastern tip of O’ahu, we found Makapu’u Beach while driving along the Kalaniana’ole Highway (Hwy 72). This beach had a beauty all its own with a combination of sandy stretches, volcanic rock and beautiful turquoise water. This area is a favorite for body surfing, but like Waimea Bay, the surf conditions can be extreme and are recommended for expert surfers only. When we arrived and laid out our towels and beach chairs, we were welcomed by the famous castaway, Wilson (the volleyball)!

From Makapu’u Beach, you can also hike the 2.5-mile paved trail to the Makapu’u Lighthouse located on the easternmost tip of O’ahu. The Makapu’u Trail offers panoramic views of O’ahu’s southeastern shoreline and a perfect spot to watch for humpback whales during their migration season, November to May.

Hanauma Bay State Park

Also located in the southeastern region is Hanauma Bay State Park, another favorite location for snorkeling. Our visit to Hanauma Bay was a highlight of my trip to O’ahu. While snorkeling around the reef among schools of colorful fish, I looked down just in time to witness a green sea turtle swim beneath me!

Unlike other beaches, Hanauma Bay is a protected area and requires advance reservations (available online). A maximum of 1,400 visitors are allowed daily and everyone entering the park is required to watch a 9-minute orientation video prior to entry. Snorkel gear is available to rent. Visitors must enter the park between 6:45 a.m. and 1:30 p.m.

Tours

Whether your interest lies in O’ahu’s history during World War II, exploring its diverse flora and fauna, or adventurous tours through remnants of iconic movie sets, there is truly something for everyone.

Pearl Harbor

Visiting Pearl Harbor gave me ALL the feels. World War II occurred during my grandparents’ time, but I’ve long had a fascination with the “greatest generation.” Walking through the Visitor Center, reading and listening to stories of the notorious attack at Pearl Harbor, took me back in time. I actually cried as I listened to some of the personal accounts and reflected on what life must have been like, not only during that era, but every day since for all those who were there.

Pearl Harbor offers a number of options for experiencing the different historic sites - including inter-island tour options for those not staying on O’ahu. We chose to purchase the self-guided audio tour passport that included admission to the Visitors Center, Aviation Museum, the Battleship Missouri and the Pacific Fleet Submarine Museum.

Kualoa Ranch

Kualoa Ranch is a nature reserve covering 4,000 acres on O’ahu’s windward coast. It is not open for self-guided tours, but instead offers several opportunities for full- or half-day guided tour experiences. Options range from peaceful beach and water sport days at Secret Island Beach, to high adventure UTV Raptor and Zipline tours. Kualoa Ranch also offers visitors opportunities to learn about their sustainability efforts.

As you explore Kualoa Ranch, expect to see expansive vistas of the ocean, valley and meadows; and maybe even relics left behind from movie sets featured in Hollywood classics including Pearl Harbor, Kong and Jurassic Park.

Waimea Botanical Gardens

There are several botanical gardens scattered around O’ahu. While simply driving around or hiking the many trails on the island will naturally share Hawaii’s tropical beauty with you, the botanical gardens give you something extra.

We toured the Waimea Botanical Gardens on the northern side of O’ahu, across from Waimea Bay Beach Park. The garden features more than 5,000 tropical, subtropical, native and globally endangered plant species. The self-guided tour wanders along a paved, 3/4-mile path. Along the way, you might see Waimea Falls (swimming optional when allowed based on weather conditions), native birds, Hawaiian cultural sites and resident artisans. There’s also a snack bar and coffee house where you can sit and enjoy the beauty surrounding you.

Restaurants, Breweries & Food Trucks

Part of the fun in traveling is experiencing local cuisine. Hawaii is no different. We enjoyed the tropical fruits, fresh seafood and local breweries as we wandered around the island. We also enjoyed the opportunity to cook several meals at our VRBO, saving on our dining out budget and enjoying some much-needed down time after days spent hiking, snorkeling and experiencing all that O’ahu has to share. Most (but not all) days we started with breakfast cooked at our house, packed snacks for the day, then enjoyed a BBQ dinner on the lanai, watching the sunset. Between breakfast and dinner, we found local restaurants, breweries and food trucks to satisfy our desire to eat like a local.

After our sunrise hike up the Lanikai Pillbox trail, we treated ourselves to a hearty breakfast at Boots & Kimo’s Homestyle Kitchen. Banana pancakes topped with macadamia nut cream are a Hawaiian specialty and the shrimp omelet was perfect for our seafood-loving wanderer.

Fish Market & Nico’s Pier 38 Restaurant

Nico’s Pier 38 is open for breakfast, lunch and dinner, as well as a Pupu (small plate) Happy Hour. We enjoyed breakfast at Nico’s after an early start one morning, getting to the pier before sunrise, just as the fishing boats were coming in with the day’s catch. Before breakfast, we watched as the boats were unloaded, then wandered through the fish market and auction. So… much… fish! By 8 a.m., we'd already explored the pier, watched the sun rise and enjoyed breakfast by the water at Nico's.

Breweries

Fun fact about us… We met on a blind date at Sierra Nevada Brewery in Northern California, so craft breweries have become something we seek out as we wander the world. On O’ahu we had lunch at Honolulu Beerworks after a hike to Manoa Falls, and recharged with dinner on the open-air patio at Kono Brewing Company after a challenging hike up the Koko Head Stairs.

Food Trucks

I know some people shy away from food trucks, but let me tell you, there’s often not much more local and authentic than what you can find there. We had a lunch of fresh shrimp at Romy’s Kahuku Prawns & Shrimp roadside shack; Portuguese-style, deep-fried doughnuts from Leonard’s Malasadamobile; and sipped fresh coconut water through a straw stuck in an actual coconut!

Luaus & Island Entertainment

A Hawaiian luau is a must when visiting the islands and there are several to choose from. We decided to spend an afternoon exploring the Polynesian Cultural Center, then stay for the evening show and luau that night. The Polynesian Culture Center was fun and filled with "happy people." My kind of place!

Time to visit Hawaii

“When nothing is sure, everything is possible,” a message that spoke to me among the Kaka’ako Street Art murals and continues to inspire me today. We spend a lot of time working and caring for others and there are times when we question a lot. But wandering the world and experiencing different locations and cultures through the eyes of the people we meet along the way brings joy and hope for the future. The “aloha spirit” of Hawaii, embracing peace, kindness, connection and ohana (family) is no exception.

Aloha, fellow wanders.

O’ahu, Hawaii … A hiker’s paradise

Hikes on O’ahu

Beaches

Tours

Restaurants, Breweries & Food Trucks

Beach Biking, Oyster Eating | Hilton Head Island Road Trip