Journeying across the vast Pacific to reach Hawaii is no quick jump, which means once there, visiting more than one of its islands holds understandable appeal. Luckily, short interisland flights make multiple-isle itineraries easy, while your travel style can determine which islands are right for you.
Here are three pairings, plus an extended three-island journey for supersizing your aloha spirit.
As always, check for travel guidelines and closures before planning your trip.
First-Timer Families: Oahu + Maui
Combine the thrill of discovery with some hands-on learning — cleverly disguised as lots of fun — on Hawaii’s two most dynamic islands.
Start your journey in Oahu unwinding on Waikiki Beach, where you can splash in the warm water, take surfing lessons from Waikiki Beachboys and ride in their outrigger surfing canoes.
Cool off at Island Vintage Shave Ice, which uses local fruit for its colorful syrups that drench heaps of fluffy ice, and at Waikiki Aquarium, where you’ll cross paths with wavy-lipped giant clams, bright corals and reef fish.
Beyond Waikiki lie the serrated green mountains and white sand beaches of Oahu’s lush windward side. At Kualoa Ranch, a popular Hollywood backdrop, embark on guided adventures by horseback, e-bike, all-terrain vehicle or other transport. Or delve into Hawaiian culture by tending a taro patch or thatching a grass hut with the ranch’s Malama Experience. Malama Hawaii means “to care for or give back to Hawaii,” and the experience promotes cultural education and helps visitors understand their kuleana (responsibility) to this sacred place.
The Polynesian Cultural Center offers a full day of interactive immersion into six Pacific Islander cultures, with an optional evening luau and a performance showcasing their culture and traditions. On the equally rural North Shore, swim under a 45-foot waterfall surrounded by botanical gardens in Waimea Valley.
Island Hop: Head from Honolulu to Kahului (Maui) on one of Southwest or Hawaiian airlines’ frequent 40-minute flights.
Once you’ve landed in Kahului, check out the nearby Maui Tropical Plantation, which provides kid-friendly zip lines, a narrated train ride with fruit tastings, and local produce in its dining outlets.
For an ocean adventure, go snorkeling or winter whale-watching aboard an eco-friendly Trilogy sailing catamaran. Alternatively, landlubber kids can admire native green sea turtles and other marine life at the Maui Ocean Center in Central Maui.
Allow time for play on West Maui’s Kaʻanapali Beach or South Maui’s Wailea and Ulua beaches, both with boardwalks leading to shops and restaurants.
Nature Lovers: Maui + Hawaii Island
Known for their towering volcanoes, these two islands boast the widest variety of terrains for enjoying native flora and fauna.
In Central Maui, pop into Iao Valley State Monument, an emerald enclave with a short hike to a soaring natural pillar. Volunteer with Kipuka Olowalu to restore a hidden valley in the West Maui Mountains.
Alternatively, explore Kapalua, home to bays ideal for snorkeling, as well as nearby options to go horseback riding, ziplining and more.
Spend a full day driving the undulating Road to Hana, which connects the waterfall-lined gulches of Maui’s North Shore and East Side; drive with aloha by parking and hiking only at permitted places, such as Twin Falls and the black sand beach of Waianapanapa State Park (reservations required).
Take another full day, and a jacket, driving to the summit of Haleakala (“house of the sun”) in Haleakala National Park, home to rare silversword shrubs and lunarlike trails; alight at eclectic Kula Botanical Garden en route.
Island Hop: Take Hawaiian Airlines’ 35-minute jet service from Kahului in Maui to Kona on Hawaii Island, or Mokulele Airlines‘ 45-minute flight in an exhilarating turboprop.
Near the Kona airport on Hawaii Island’s west side lies Kaloko-Honokohau National Historical Park, home to ancient fishponds, rich bird life and basking green sea turtles. Take a snorkeling tour of Kealakekua Bay and its kaleidoscopic reef fish or an evening snorkel with manta rays near Keauhou Bay; Fair Wind offers thoughtful versions of each.
Head to the island’s east side for the impressive waterfalls of Akaka Falls State Park, where a paved loop passes through giant bamboo and torch ginger. The abundant foliage and waterfalls of Hawaii Tropical Bioreserve & Garden lie off the suitably named Four-Mile Scenic Drive near Hilo.
In Hawaii Volcanoes National Park, a network of trails wind through giant ferns and ohia lehua trees and across cinders and mounds of hardened lava on the flanks of still-active Kilauea Volcano. With luck, you’ll witness oozing lava in enormous Halemaumau Crater.
Follow Saddle Road between the active Mauna Loa and long-dormant Mauna Kea volcanoes for easy bird-watching hikes. Stargazing on 13,803-foot Mauna Kea is also superlative. Book Hawaii Forest & Trail’s Maunakea Summit & Stars Giveback tour to add a conservation stop at Waikoloa Dry Forest, an oasis of rare wiliwili trees.
Luxury & Shopping: Oahu + Maui
Luxury travel to Hawaii first gained favor on Oahu with the historic hotels of Waikiki Beach, while Maui’s modern resorts have furthered the concept with sumptuous spas. The two most populous isles are also tops for shopping.
In Oahu, check into Waikiki Beach’s iconic pink palace, The Royal Hawaiian, a Luxury Collection Resort, Waikiki, or one of the chic ocean-view condos of The Ritz-Carlton Residences, Waikiki Beach. Then walk to the international designer boutiques of Luxury Row and the Royal Hawaiian Center, where House of Mana Up showcases Hawaii’s rising designers and makers.
Head downtown to Iolani Palace for a look at the finery of Hawaii’s monarchy and a poignant lesson on its 1893 overthrow. Stroll the sprawling Ala Moana Center for more designer shopping, or sample the wares of diverse local artists, chefs and makers in the urban Kakaako district and Chinatown.
Island Hop: Hawaiian, Southwest and Mokulele all fly to Kahului in Maui from Honolulu; Mokulele also flies to Kapalua.
After arriving in Maui, sightsee by shopping your way across the island. At the Shops at Wailea, close to South Maui’s inviting beaches, you’ll find the work of local artists and artisans at Maui Hands, along with Prada, Gucci and other elite labels. Check the outdoor mall’s weekly schedule for free cultural activities such as lei-making and a Polynesian show.
Local designers of beachwear, jewelry and home decor add a chic note to the bohemian beach village of Paia and the Upcountry cowboy town of Makawao.
Save time for a luxurious spa day at your resort, especially a massage with hot volcanic rocks and a scrub with coconut and sugar.
Multiweek Island Adventure: Oahu + Maui + Hawaii Island
Time will still fly even on a two-week trip to the islands, so carefully choose your favorite activities from the itineraries above and then add these bonus diversions.
Oahu bonus activities: Immerse yourself in the history of the December 7, 1941, attack on Pearl Harbor and World War II in the Pacific in and around the Pearl Harbor National Memorial. Highlights include the sobering, sunken USS Arizona Memorial (reservations required), the USS Bowfin Submarine Museum & Park, the twin hangars and control tower of the Pearl Harbor Aviation Museum, the Battleship Missouri Memorial (the site of Japan’s surrender) and the hauntingly tranquil National Memorial Cemetery of the Pacific.
Island Hop: Go from Honolulu to Kahului, Maui, on a Southwest, Hawaiian or Mokulele flight.
Maui bonus activities: Surfing Goat Dairy and Hawaii Sea Spirits Organic Farm & Distillery in Upcountry Maui and Maui Kuia Estate Cacao Farm offer fascinating farm tours along with delectable products and sweeping vistas.
Island Hop: Leave Kahului for Kona on Hawaii Island on a Hawaiian or Mokulele flight.
Hawaii Island bonus activity: Travel the winding roads of Kona coffee country, stopping for a tour, tastings and a nature walk at Mountain Thunder or a “roast your own” session at UCC Hawaii. Nearby, learn about Hawaiian traditions in a gorgeous shoreline setting at Puuhonua o Honaunau National Historical Park, a historic place of refuge.
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