The Ultimate Hawaiian Island-Hopping Itinerary

Touch down at Hilo International (ITO), either via direct flight or connecting through 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 replete with historical and cultural sites. Discover native culture while soaking up the ocean views at Kaloko-Honokohau National Historical Park, famous for its lava beaches, petroglyphs, abundance of endangered sea turtles and the Aiopio Fishtrap, a fascinating formation of lava rocks traditionally used as a natural fish trap. Take a backcountry hike and fill your camera with photos of haunting wooden sculptures on a self-guided tour of Puuhonua o Honaunau National Historic Park, a sacred Hawaiian site. Historic Kailua Village was once a playground for Hawaiian royalty and home of King Kamehameha I in the early 1800s. After viewing the historic Ahuena Heiau temple, Hulihee Palace and Mokuaikaua Church, finish the day with dining 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 in a mahogany boat.

On the island’s eastern coast, the Hilo region was the cradle of Hawaii’s sugar industry in the early 19th century. Today, it’s a popular spot for shopping, tropical beauty and its proximity to Hawaii Volcanoes National Park. Start the day by filling shopping bags with colorful local produce, baked goods and handicrafts from more than 200 vendors at 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’ll be treated to views of the 135-meter-tall waterfall set amid lush vegetation and wild orchids. Check into the Grand Naniloa Hotel Hilo – a DoubleTree by Hilton on picturesque Hilo Bay to wind down for the day. Enjoy local flavors while dining at Hula Hulas restaurant and check out the live hula performances on Monday afternoons. You’re off to new adventures on Oahu in the morning.

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 Pacific Ocean waters are calling, so reserve a tour aboard the Spirit of Aloha, a luxury catamaran out of Port Waikiki. The excursion includes a sail along the coast, sightings of seasonal whales and glimpses of sea turtles while snorkeling in Turtle Canyon. Back on land, check out Honolulu’s street art in the vibrant Kakaako District, which hosts the annual Pow! Wow! Hawaii art festival in February, and sate your appetite with fresh seafood and regional cuisine. The Hilton Hawaiian Village Waikiki Beach Resort offers ideal overnight lodging. On-site activities include an exciting luau, ukulele and lei-making lessons, and stand-up paddleboarding in the lagoon. Surf’s up at your next stop: Oahu’s North Shore.

The North Shore of Oahu is synonymous with surfing, and the sport’s biggest names come here to conquer the powerful waves. The winter months, from November to February, are when the surf is the most impressive. Unless you’re a professional, though, winter surfing is best experienced from the shore as a spectator. Waimea Bay, where big-wave surfing was born, is a good spot to relax and watch the pros. In Haleiwa Town, cool down at Matsumoto Shave Ice, a North Shore mainstay since 1951, where you’ll have your pick of 37 flavors of handmade shaved ice. Before leaving Oahu, consider visiting other iconic island attractions, including Diamond Head State Monument and World War II Valor in the Pacific National Monument at Pearl Harbor. Book a direct flight to Kauai to continue your excursion.

Catch a flight from Honolulu to Lihue (LIH) on Kauai, nicknamed the Garden Island for its verdant mountains, thick rainforests and sparkling waterfalls, including Wailua Falls, an easily accessible, two-tiered cascade with dramatic scenery. Drive through Tree Tunnel lined with 500 100-year-old eucalyptus trees, to visit the historic buildings at 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 botanical products, including Hawaiian bath salts, lip balms and candles. While you’re in the South shore region, check out the six-meter-high blowhole at Spouting Horn (be sure to abide by all signage and do not cross barriers) and stroll along Poipu Beach Park, where you might spot whales or sea turtles. Save a few hours to go hiking at Waimea Canyon State Park, called the Grand Canyon of the Pacific for its 16-kilometer long, 1,000-meter-deep canyon. Check into the Hilton Garden Inn, Kauai Wailua Bay for beachside accommodations before your flight to Maui.

From Kauai, board a flight to Kahului (OGG) on Maui, and marvel at nature’s beauty everywhere. Go hiking at Iao Valley State Park to the 366-meter-tall Iao Needle, site of the notorious 1790 Battle of Kepaniwai. The nearby town of Wailuku, historically significant in the sugar industry, features mom-and-pop shopping and dining along historic Market Street. Next, drive to the hippie town of Paia, where you can browse local shops and photograph the beautiful Stupa at the Maui Dharma Center. Continue inland driving along 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; linger there into the night to gaze at the stars. Treat yourself to a stay at the Grand Wailea, A Waldorf Astoria Resort. In addition to an impressive art collection, upscale shopping and diverse dining options, the resort offers scuba lessons, beach yoga, outrigger canoe tours and an unforgettable pool complex complete with the world’s only water elevator, a rope swing and the 80-meter-long Lava Slide. Drive 27 kilometers to Kahului International to return your car and board your flight home.