Before you begin to chuckle at the idea of road tripping on an island, hear us out. A road trip in Hawaii is all about taking your time to experience the beauty around you, whether it's hopping out of the car to explore a rainy waterfall trail, finding a hidden banana bread stand, or feeling the breeze from a scenic lookout over the Pacific Ocean. Thanks to the unparalleled allure of these island road trips, you won’t be disappointed.
Road to Hana, Maui
The granddaddy of all Hawaiian road trips, the famous Road to Hana is deceptively long. The drive has 620 notorious curves, 54 bridges, and follows the rugged, undeveloped Hana Highway through some of the most beautiful terrain Hawaii has to offer. It may only be 52 miles long, but the twists, turns, and highlights will take anywhere from three to five hours to complete each way.
Start in the sleepy surfing town of Paia, a unique destination in itself. Grab some breakfast at one of the many trendy eateries in town, such as Paia Bay Coffee Bpmar or the Kuau health food store for snacks. You can always keep an eye out for local banana bread stands throughout the drive if you run out of snacks; Some of the best can be found at the Twin Falls stand and Halfway to Hana stand.
The Road to Hana is famous for its waterfalls, and there are a lot of them. Be sure to make stops at Twin Falls, Upper Waikani Falls, Hanawi Falls, and Wailua Falls, most of which are located just off the road. This journey isn’t just about waterfalls, though. Be sure to pull over and spend some time at Keʻanae Peninsula for some incredible views of the volcanic Maui coastline, the Garden of Eden botanical gardens, Waiʻānapanapa State Park to see the black sand beaches, and the lava tube at Kaʻeleku Cave. End your journey at white-sand Hamoa Beach or hike the Pipiwai Trail in the Kīpahulu District of Haleakala National Park. Be sure to give yourself enough time to make the drive back before dark, or opt to spend a night in Hana town to split the journey in half.
Windward Oahu to North Shore Oahu
The North Shore of Oahu is a true highlight for plenty of visitors, though most choose to save time by taking the easy way up through the center of the island. Instead, we challenge you to get out of the city and cruise 60 miles through windward Oahu via the Kalanianaʻole and Kamehameha Highways.
Start at the lookout for Hanauma Bay Nature Preserve. It's one of the island’s most popular snorkeling destinations, but you don’t have to get into the water to enjoy the place. Around 2 miles up the road, you’ll find the Halona Blowhole lookout with views of Cockroach Cove, also known as “From Here to Eternity Beach.” If you’re in the mood for nature spend some time at the Hoʻomaluhia Botanical Garden, a 400-acre garden in a tropical rainforest at the base of the Koʻolau mountain range. Stop to ring the peace bell and pay your respects at the Byodo-In Temple in Kaneohe before learning the history of the Polynesian Islands at the Polynesian Cultural Center in Laie.
Further up Kamehameha Highway, stop at Kualoa Ranch for a trail ride on horseback or a movie tour at Kualoa Ranch or pull over to see Chinaman's Hat (Mokoliʻi Island) just across the road. Try out one of the shrimp trucks in Kahuku, such as Romy’s, Fumi’s, or Giovanni’s, for lunch. Or, get a plate lunch and a slice of pie at Ted’s Bakery closer to Haleiwa Town. Some other great options once you reach the north side of the island include the Turtle Bay Resort, Waimea Valley, and Haleiwa’s main street lined with local restaurants and shops.
This 20-mile drive through Upcountry Maui will take you away from the famous Maui coastline and up into the rural areas on the slopes of Haleakala.
Start in the Paniolo cowboy town of Makawao, where rustic and modern aesthetics combing in the many boutiques, restaurants, and art galleries. Go south down Highway 37, stopping in Kula where you can take a distillery tour of local organic Ocean Vodka, identify Hawaiian plants and flowers at the Kula Botanical Gardens, enjoy mountain views on a tour of the lavender gardens at Aliʻi Kula Lavender, or milk a goat at the Surfing Goat Dairy Farm.
End the day tasting wine or simply enjoying the scenic vineyards at Maui Wine in Ulupalakua, where you can pineapple wine produced 2,000 feet above sea level.
Hamakua Coast, Hawaii Island
Hawaii Island is known for driving. As the largest island in the state—bigger than all the other islands combined, in fact—you will definitely need a set of wheels to get from point A to point B. With its distinctive combination of terrains from rugged and rocky to verdant and humid, the 50-mile journey along the Hamakua Coast in northeastern Hawaii Island will be sure to take your breath away.
Start at Rainbow Falls in Hilo for a super-accessible view of the 80-foot waterfall known for its powerful spray, forming rainbows when the sunlight hits just right. From there, head up Hawaii Belt Road (Highway 19) stopping at the Hawaii Tropical Bioreserve & Garden, Akaka Falls State Park, and Laupahoehoe Point, all the while with the profile of majestic Mauna Kea volcano to your left. End your journey at historic Waipiʻo Valley, the spectacular curved valley that a young King Kamehema I called home as a boy. Find one of the best spots to experience the valley off of Kukuihaele Road, where the Waipiʻo Valley Overlook offers sweeping views of the 5-mile-deep ravine and 2,000-foot-tall cliffs.
North Shore Kauai
Take advantage of all 16 miles of this North Shore Kauai road trip, which packs a punch with plenty of highlights despite its short length. This side of Kauai is known for lush flora and rainy weather, which is truly saying something considering Kauai is the wettest island in the state.
Start at Kilauea Point National Wildlife Refuge & Lighthouse to spot some rare Hawaiian seabirds or spinner dolphins off the coast and check out the 100-year-old lighthouse. On your way past Princevilles’s green golf courses to famed Hanalei Town via Route 56 (Kuhio Highway), you can stop at one of the small beaches or hike down to the ocean tidepools at Queen’s Bath. Stop in Hanalei to lounge on the beach near Hanalei Pier, shop, or have lunch before continuing on towards Hāʻena State Park. Along the way to Hanalei, be sure to keep an eye out for the elusive Nene goose, the state bird, as you drive through Hanalei National Wildlife Refuge.
End your road trip at the entrance to Nā Pali Coast State Park to hike a portion of the stunning Kalalau Trail or snorkel at Keʻe Beach. Heading back in the evening, hit up Bar Acuda in Hanalei for some island-inspired tapas for dinner.