Best Hikes in Oahu: Hikes for Everyone in Your Group!

The Classic Adventurer: Diamond Head
Difficulty: Moderate

The classic adventurer can’t help but give into the FOMO of the most popular hike on the island. Diamond Head, the iconic volcanic crater, beckons adventurers with its panoramic views of Waikiki and the Pacific Ocean. The moderate climb to the summit offers not just incredible scenery but also a glimpse into history as you pass by historic military bunkers. Take a moment to catch your breath at the top and marvel at the breathtaking vistas sprawling before you, making this one of the best hikes in Oahu and a quintessential unique to the island experience for those seeking adventure and stunning landscapes.

The Crossfit Friend - Koko Crater
Difficulty: Strenuous

The crossfit friend loves getting their sweat on and craves telling people about their intense workouts. For such a fitness enthusiast and craver of challenge, Koko Crater presents an exhilarating ascent along a steep railway track. With over a thousand steps to conquer, this hike tests your endurance while offering unparalleled views of the southeastern coastline and the crater's interior. As you make your way up, feel your heart racing not just from the workout but also from the awe-inspiring scenery surrounding you, making every step worth the effort.

The Up & Coming Influencer - Lanikai Pillbox
Difficulty: Easy to Moderate

Calling that one person in the group who always gets the best shot! The Lanikai Pillbox trail promises insta-worthy views of Lanikai Beach and the Mokulua Islands. This relatively easy hike offers plenty of opportunities to capture stunning sunrise or sunset shots from the iconic pillbox vantage points. As you stroll along the trail, be sure to admire the vibrant wildflowers dotting the landscape and keep an eye out for native bird species, creating an unforgettable experience for shutterbugs and nature lovers alike. It’s no wonder this perfect picture is one of the best hikes in Oahu.

The Strollers - Makapuʻu Lighthouse Trail
Difficulty: Easy

Gather the family for a leisurely hike along the Makapuʻu Lighthouse Trail, offering sweeping coastal views and the chance to spot humpback whales during the winter months. The paved path and gradual incline make it accessible to all ages, providing the perfect opportunity for a lovely stroll immersed in nature's beauty. Pause at the lighthouse to admire its historic charm and take in the breathtaking vistas.

The Waterfall Chaser - Waimano Falls
Difficulty: Moderate

For this friend, no hike is complete without a water feature. Delve into the heart of Oahu's wilderness with a hike to Waimano Falls, a hidden gem tucked away in a lush valley. This moderate trail rewards hikers with a refreshing waterfall and serene natural surroundings, offering the perfect escape for nature lovers. As you navigate through the verdant forest and cross meandering streams, feel a sense of tranquility enveloping you, making this hike a peaceful retreat amidst Hawaii's stunning landscapes.

The Wildlife Enthusiast - Kaena Point Trail
Difficulty: Easy

For the friend that feels the most at home when surrounded by wildlife friends. Explore the westernmost tip of Oahu along the Kaena Point Trail, where dramatic cliffs meet the sea. This leisurely coastal walk offers excellent opportunities for birdwatching, particularly the endangered Laysan albatross and Hawaiian monk seals. As you stroll along the trail, breathe in the salty ocean air and soak in the rugged beauty of the coastline, creating unforgettable encounters with Hawaii's diverse wildlife.

The Adventure Seeker - Lanipo Trail
Difficulty: Challenging

For the adventurous souls craving an off-the-beaten-path experience, Lanipo Trail awaits. This lesser-known gem offers a challenging ascent through dense vegetation to panoramic views of Honolulu and the Windward Coast. As you navigate through the rugged terrain, feel a sense of exhilaration with each step forward, rewarded by the breathtaking vistas awaiting at the summit. It's an unforgettable journey for experienced hikers seeking adrenaline-fueled adventures in Hawaii's wilderness.

The Reward Motivated Friend - The Maunawili Falls
Difficulty: Moderate

Not only does this hike feature a beautiful swimming hole but after you finish, head over to Moke’s Bed & Breakfast for an incredible stack of Lilikoi Pancakes to congratulate yourself for a job well done. Embark on a picturesque hike to Maunawili Falls, nestled amidst lush rainforest scenery. This moderate trail features some muddy terrain and stream crossings, but the reward of swimming beneath the cascading waterfall makes it all worthwhile. As you immerse yourself in the natural beauty of the surroundings, feel the cool mist on your skin and listen to the soothing sound of water tumbling down.

The Zen Seeker - Kuliʻouʻou Ridge Trail
Difficulty: Moderate

The perfect trail for the friend that just finished their Yoga Training in Bali and starts every morning off with a meditation. Find peace and serenity on the Kuliʻouʻou Ridge Trail, offering a gentle ascent through native forest and panoramic vistas of the Windward Coast. This meditative hike provides the perfect escape from the hustle and bustle of everyday life, allowing you to reconnect with nature and soothe your soul. As you meander along the trail, breathe in the crisp mountain air and bask in the beauty of the surrounding landscape, creating a sense of inner peace and tranquility amidst Hawaii's natural wonders.

So, whether you're craving heart-pounding thrills or laid-back vibes, these top hiking spots have you covered. Strap on your boots, grab your water bottle, and get ready to hit the trails for an unforgettable journey through Hawaii's natural wonders. And hey, if you need any tips or tricks along the way, I've got your back. From finding you the perfect hotel to the perfect way to spend your time each day, I’d be happy to help you build the Hawaiian Vacation of your dreams. Let's make this vacation the best one yet!

This trip report is part of our ongoing series on travel to Oahu.