The tropical archipelago of Hawaii is as remote as it is awe-inspiring.
It’s where evergreen rainforests and towering waterfalls meet urban excitement, native culture and unique history. With six major Pacific islands to explore, it can be hard to choose where and how to experience Hawaii. This epic fly and drive itinerary encourages you to visit multiple islands for an unforgettable adventure.
Ancient History in Kailua-Kona, Hawaii
Land at Hilo International (ITO), either via a direct flight or connecting via Honolulu International (HNL). Pick up your rental car and begin your journey on the island of Hawaii, the largest of the islands. From the airport, it’s just under a two-hour drive across the island to the Kona region, which is packed with historical and cultural sites. Discover native culture while taking in ocean views at Kaloko-Honokohau National Historical Park, famous for its lava beaches, petroglyphs, abundance of endangered sea turtles, and the Aiopio Fish Trap, a fascinating rock formation of lava that is traditionally used as a natural fish trap. Take a hike through the countryside and fill your camera with photos of haunting wooden sculptures on a self-guided tour of Puuhonua o Honaunau National Historical Park, a sacred Hawaiian site. The historic town of Kailua was once a playground for Hawaiian royalty and the home of King Kamehameha I in the early 19th century. After seeing the historic Ahuena Heiau Temple, Hulihee Palace, and Mokuaikaua Church, end the day with dinner and drinks in the village. Hilton Waikoloa Village, a short drive up the coast, offers stunning oceanfront rooms and activities, including dolphin encounters, a luau, and canal rides on a mahogany boat.
Exploring Like a Local in Hilo, Hawaii
On the island’s east coast, the Hilo region was the cradle of Hawaii’s sugar industry in the early 19th century. Today, it is a popular place for shopping, enjoying the tropical beauty, and its proximity to Hawaii Volcanoes National Park. Start the day by filling shopping bags with colorful local produce, baked goods and crafts from more than 200 vendors at the Hilo Farmers Market. Head to Akaka Falls State Park, a popular stop along the Hamakua Coast, for a leisurely hike on the Akaka Falls Loop Trail. You will enjoy views of the 135 meter high waterfall set amidst lush vegetation and wild orchids. Check into the Grand Naniloa Hotel Hilo, a DoubleTree by Hilton in picturesque Hilo Bay to relax for the day. Enjoy local flavors as you dine at the Hula Hulas restaurant and watch live hula performances on Monday afternoons. You’re leaving for new adventures on Oahu in the morning.
Fun on the Water in Honolulu and Waikiki Beach, Oahu
It’s a one-hour flight from Hilo International to Honolulu International, where you can pick up another rental car and explore the attraction-rich island of Oahu. The pristine waters of the Pacific Ocean are calling to you, so book a tour aboard the Spirit of Aloha, a luxury catamaran departing from Port Waikiki. The excursion includes a cruise along the coast, seasonal whale watching, and sea turtle sightings while snorkeling in Turtle Canyon. Back on land, check out Honolulu’s street art in the vibrant Kakaako district, home to the Pow! Wow! Hawaii Arts Festival in February and satisfy your appetite with fresh seafood and regional cuisine. The Hilton Hawaiian Village Waikiki Beach Resort offers an ideal accommodation for an overnight stay. On-site activities include an exciting luau, ukulele and lei lessons, and paddle boarding in the lagoon. Surf your next stop: Oahu’s North Shore.
Big Waves and Big Flavor on the North Shore, Oahu
Oahu’s North Shore is synonymous with surfing, and the biggest names in the sport come here to conquer the powerful waves. The winter months, from November to February, are when the waves are most impressive. However, unless you are a professional, winter surfing is best experienced from the shore as a spectator. Waimea Bay, where big wave surfing was born, is a good place to kick back and watch the pros. In Haleiwa Town, cool off at Matsumoto Shave Ice, a North Shore mainstay since 1951, where you can choose from 37 flavors of handmade shaved ice. Before you leave Oahu, consider visiting other iconic island attractions such as the Diamond Head State Monument and the WWII Valor in the Pacific National Monument at Pearl Harbor. Book a direct flight to Kauai to continue your excursion.
Outdoors, Nature and Local Charm on Kauai
Take a flight from Honolulu to Lihue (LIH) on Kauai, nicknamed the Garden Isle for its verdant mountains, thick rainforests, and sparkling waterfalls, including Wailua Falls, an easily accessible two-tier waterfall with spectacular scenery. Drive through the Tree Tunnel lined with 500 100-year-old eucalyptus trees to visit the historic buildings in Old Koloa Town. Shops and restaurants are housed in restored sugar plantation buildings and sell everything from handmade soaps to Hawaiian art, Kauai coffee and shaved ice. At Island Soap & Candle Works, peruse the botanicals, including Hawaiian bath salts, lip balms, and candles. While you’re in the South Shore region, check out the 20-foot-tall blowhole at Spouting Horn (make sure to abide by all signs and don’t cross the barriers), and stroll through Poipu Beach Park, where you might spot whales or fish marines. turtles Save a few hours to hike Waimea Canyon State Park, called the Grand Canyon of the Pacific for its 10-mile-long, 3,000-foot-deep canyon. Check into the Hilton Garden Inn, Kauai Wailua Bay for beachside accommodations before your flight to Maui.
Final Stop: Incredible Parks and Luxury on Maui
From Kauai, board a flight to Kahului (OGG) on Maui and marvel at the beauty of nature everywhere you turn. Hike in Iao Valley State Park to the 1,200-foot-tall Iao Needle, site of the notorious 1790 Battle of Kepaniwai. The nearby town of Wailuku, historically significant in the sugar industry, has family-owned shops and restaurants along the from historic Market Street. Next, head to the hippie town of Paia, where you can browse the local shops and photograph the beautiful Stupa at the Maui Dharma Center. Continue inland driving down the windy Haleakala Highway to reach Haleakala National Park. Make a reservation in advance to watch the sun rise from the summit. Equally impressive are the sunsets; stay there at night to gaze at the stars. Enjoy a stay at the Grand Wailea, a Waldorf Astoria Resort. In addition to an impressive art collection, unique shops, and diverse dining options, the resort offers scuba classes, beach yoga, canoe tours, and an unforgettable pool complex featuring the world’s only water elevator, a rope swing, and the 80 meters long. Lava slide. Drive 27 kilometers to Kahului International to return your car and board your flight home.
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