Lacks tree cover and can be vulnerable to sun, wind, or drop-offs.
Tucked away on Oʻahu’s leeward coast, the Maili Pillbox hike feels like a secret trail known mostly to locals. While sunrise seekers flock to Lanikai or Pink Pillbox, this lesser-known path rises quietly above the sleepy neighborhood of Māʻili, offering breathtaking ocean views without the crowds. It’s a place where the ridgeline unfolds in soft golden light, the sea glitters endlessly in shades of turquoise, and the air carries the warmth of the island’s dry west side.
Tucked into the verdant slopes above the city, the Honolulu Watershed Forest Reserve is one of Oʻahu’s most vital yet underappreciated natural treasures. This vast expanse of protected land, stretching across ridges, valleys, and mountain peaks, safeguards the island’s freshwater supply while preserving an extraordinary range of native ecosystems. For visitors, it offers a rare chance to step into a world where towering ʻōhiʻa trees, lush ferns, and the songs of native birds fill the air—a living reminder of Hawaiʻi’s natural heritage.
Tucked between Diamond Head and Koko Head, the Kāhala Lookout is a lesser-known roadside stop that offers peaceful views of the Kāhala coastline and the Pacific Ocean beyond. It’s not a major destination, but it provides a welcome breath of fresh air for travelers enjoying a slow, scenic drive along Oʻahu’s south shore.
Just a short drive from downtown Honolulu, the Lulumahu Falls Trail leads to a secluded waterfall nestled deep within Nuʻuanu Valley. Though unofficial and unmaintained, this trail has become a favorite among locals and visitors looking to step off the beaten path and into the heart of Oʻahu’s lush interior.
Just a short drive from Honolulu’s bustling city center, the Tantalus Lookout at Puʻu ʻUalakaʻa State Park offers one of Oʻahu’s most breathtaking urban views. From the lookout platform, you can see the full sweep of the Honolulu skyline, the turquoise waters off Waikīkī, and Diamond Head rising proudly in the distance. As the sun sets, the entire scene transforms into a golden panorama with the city lights beginning to twinkle below.
At the far western tip of Oʻahu, where the paved roads end and the coastline turns wild, the Kaʻena Point Trail leads to one of the island’s most remote and untouched natural areas. This relatively flat but rugged coastal walk can be accessed from either the North Shore near Mokulēʻia or the west side near Mākaha, and both routes offer sweeping ocean views, lava rock shorelines, and a rare encounter with native Hawaiian wildlife.
High above the cliffs of the Koʻolau mountain range, the Nuʻuanu Pali Lookout offers one of Oʻahu’s most iconic views. Just minutes from downtown Honolulu, this historic site reveals a sweeping panorama of Kāneʻohe, Kailua, and the lush valleys of Oʻahu’s Windward side.
Tucked deep within a quiet valley in Hawaiʻi Kai, the Kuliʻouʻou Ridge Trail is a local favorite for those seeking a more secluded and rewarding ridge hike. This moderately strenuous route begins in a shaded forest and rises steadily to a sweeping ridgeline lookout, offering panoramic views that span from Waimānalo to Koko Crater and beyond.
Behind the world-famous surf breaks of the North Shore lies a trail less traveled but equally rewarding. The ʻEhukai Pillbox Trail begins just across from ʻEhukai Beach Park and climbs steadily through shaded forest terrain to reveal panoramic views of Sunset Beach, Pupukea, and Waimea Bay. With its mix of peaceful woods and dramatic coastal lookouts, this hike offers a quieter contrast to the bustling beach scene below.
Winding through the uplands of Keaiwa Heiau State Recreation Area, the ʻAiea Loop Trail offers a tranquil escape from Oʻahu’s more crowded corners. Tucked just above Hālawa Valley, this 4.8-mile loop meanders through groves of eucalyptus and native koa, filling the air with earthy pine scents and soft birdsong. A local favorite for its shaded paths and peaceful atmosphere, it’s the kind of trail that invites you to slow your pace and breathe deeply.