The Ultimate Road Trip Through Hawaii: Hidden Gems and Scenic Stops
Starting your journey on the island of Oʻahu, a must-visit spot is the Lanikai Pillboxes hike near Kailua, about a 30-minute drive northeast of Honolulu. This relatively short but moderately steep 1.8-mile round-trip trail rewards hikers with panoramic views of the turquoise Lanikai Beach and the Mokulua Islands. What sets this hike apart is the unique vantage point from old military bunkers—or “pillboxes”—perched atop the ridge, offering one of the most iconic photo ops in Hawaii. Early morning is the best time to go, when the light is soft, the winds are calm, and the beach below is serenely empty.
Crossing over to the Big Island, the Hawaiʻi Volcanoes National Park near Hilo, roughly an hour’s drive southwest of Hilo town, offers an immersive experience into the island’s fiery origins. Walk the Kīlauea Iki Trail, a 4-mile loop that descends into a crater floor formed by a volcanic eruption in 1959. As you traverse solidified lava and steam vents, you witness the raw power that continuously shapes the island. This park is unique because it combines live volcanic activity with lush rainforests and native wildlife. Visiting in the dry season, from April to October, often provides clearer views of volcanic glow at night, adding a dramatic spectacle to your visit.
On Maui, make your way to the historic town of Lahaina, located on the island’s west coast about 45 minutes from Kahului Airport. Once the capital of the Hawaiian Kingdom, Lahaina’s Front Street is a lively hub full of art galleries, historic sites, and oceanfront charm. Strolling along this waterfront town, you can visit the Baldwin Home Museum, the oldest house on Maui, which gives insight into early missionary life in Hawaii. The town’s vibrant sunsets over the harbor set it apart from other places on the island. Late afternoon is prime time to soak in the atmosphere, followed by dining at local seafood eateries that emphasize fresh, island-caught fish.
On Kauai, venture to the Nā Pali Coast State Wilderness Park, about a two-hour drive northwest from Lihue. The Kalalau Trail, an 11-mile one-way trek along towering sea cliffs, is a challenging but unforgettable route that leads to Kalalau Beach, one of the most pristine and secluded beaches in the state. The trail’s dramatic views of sheer emerald cliffs plunging into the Pacific and hidden waterfalls make it a standout among Hawaii’s natural landscapes. Because the trail can be dangerous during heavy rain, visiting between late spring and early fall offers safer and more pleasant hiking conditions.
Back on Oʻahu, the Bishop Museum in Honolulu is a treasure trove of Hawaiian culture and natural history, located just north of downtown. Its extensive exhibits include ancient Polynesian artifacts, royal family relics, and a vast collection of native flora and fauna specimens. The museum’s Pacific Hall allows visitors to trace the history of the islands from the earliest settlers through to modern-day life, making it a key stop to understand Hawaii beyond its beaches. Visiting on a weekday can help avoid crowds and provide a more intimate experience with the exhibits.
The island of Molokaʻi, often overlooked by tourists, invites exploration of the Kalaupapa National Historical Park, about a 45-minute drive from Kaunakakai. This remote peninsula was once a leper colony, and today visitors can learn about the resilience and stories of the patients who lived there. Access is via guided mule rides or hikes down the steep cliffs, offering both historical insight and breathtaking views over the Pacific. The park’s isolation and solemn history make it a profound place of reflection, best visited in the dry morning hours when the weather is cooler and the light illuminates the sheer cliffs beautifully.
Finally, on the island of Lanaʻi, the Munro Trail begins near Lanaʻi City, about a 15-minute drive from the small town center. This 12-mile dirt road trail winds through old Hawaiian forest and up to an elevation of over 3,000 feet, where the summit rewards travelers with sweeping views of Lanaʻi, Maui, and even Molokaʻi on clear days. The trail is unique for its quiet solitude and diverse environment, from eucalyptus groves to native plant restoration areas. Because Lanaʻi has relatively few visitors, this trail offers a rare chance to experience Hawaii’s backcountry away from the crowds. Visiting in the early morning enhances the experience, with cooler temperatures and the possibility of spotting native birds in the forest canopy.