Journeying across the vast Pacific to reach Hawaii is no quick jump, so once there, visiting more than one of its islands holds some appeal. Luckily, short interisland flights make multiple-island Hawaii island-hopping itineraries easy, while your travel style can determine which islands are right for you.
Here are three pairings, plus an extended three-island journey.
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, and paddle in outrigger surfing canoes.
Cool off at Island Vintage Shave Ice, which uses local fruit for colorful syrups that drench heaps of fluffy ice, and at Waīkikī 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, or all-terrain vehicle. Delve into traditional sustainability practices here on the Kualoa Grown Tour. Wander verdant fruit and flower gardens to see how they nourish nearby communities, and visit Mōli‘i Fishpond — a prototype Hawaiian aquaculture, estimated to date back 800 to 1,000 years.
The Polynesian Cultural Center offers interactive immersion experiences into six Pacific Islander cultures, with an optional evening luau meal or a performance showcasing their traditions.
On the equally rural North Shore of Oahu, visit Waimea Valley to swim under a 45-foot waterfall and wander lush botanical gardens.
Island Hop: Head from Honolulu to Kahului in Maui on one of the frequent 40-minute flights from Southwest Airlines and Hawaiian Airlines.
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 throughout its dining spots.
For an ocean adventure, go snorkeling or winter whale-watching aboard an eco-friendly Trilogy sailing catamaran. On land, kids can also admire native green sea turtles at the Maui Ocean Center in Central Maui.
Make some time for play on West Maui’s Kaʻanapali Beach or South Maui’s Wailea and Ulua beaches, which have great spots to splash around.
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 the flora of a valley in the West Maui Mountains.
Alternatively, explore Kapalua, home to bays ideal for snorkeling, as well as nearby options for horseback riding and ziplining.
Spend a 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 day, and a jacket, to drive to the summit of Haleakala (“house of the sun”) in Haleakala National Park, home to rare silversword shrubs and lunar-like trails. Wind through the 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.
Make your way to 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 both.
Head to the island’s east side to explore the waterfalls of Akaka Falls State Park, where a paved loop passes through giant bamboo and torch ginger. More foliage and waterfalls await at Hawai’i Tropical Bioreserve & Garden, just off the suitably named Four-Mile Scenic Drive near Hilo.
In Hawaii Volcanoes National Park, wind through a network of trails shrouded by giant ferns and ohia lehua trees atop mounds of hardened lava on the flanks of the active Kilauea Volcano. With luck, you’ll witness oozing lava in the enormous Halemaumau Crater.
Follow Saddle Road between the active Mauna Loa and long-dormant Mauna Kea volcanoes for easy bird-watching hikes. The stargazing on 13,803-foot Mauna Kea is also superlative. Book Hawaii Forest & Trail’s Maunakea Summit & Stars Giveback tour to stargaze from the summit and help out at nearby Waikoloa Dry Forest, an oasis of rare wiliwili trees.
Luxury & Shopping: Oahu + Maui
Luxury travel to Hawaii has had a longstanding base in the historic hotels of Waikiki Beach in Oahu. Maui’s modern resorts have furthered the concept with sumptuous spas. The two most populous isles are also great destinations 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 at The Ritz-Carlton Residences, Waikiki Beach. Then walk to Luxury Row for international designer shops 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 artisans in the artsy Kakaako district and Chinatown.
Island Hop: Hawaiian, Southwest, and Mokulele all fly from Honolulu to Kahului, Maui; Mokulele also flies to Kapalua, Maui.
After arriving in Maui, sightsee by shopping across the island. At the Shops at Wailea, close to South Maui’s inviting beaches, you’ll find international couture label shops and the work of local artists and artisans at Maui Hands. Check the outdoor mall’s weekly schedule for free cultural activities such as lei-making.
Local designers of beachwear, jewelry, and home decor add a chic note to the bohemian beach village of Paia and the Upcountry ranch town of Makawao.
Save time for a luxurious spa day at your resort, savoring treatments like hot stone massages and full-body scrubs at The Ritz-Carlton Maui, Kapalua.
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: Learn more about 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, the USS Bowfin Submarine Museum & Park, the twin hangars and control tower of the Pearl Harbor Aviation Museum, 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 Ocean Organic Farm & Distillery in Upcountry Maui and Maui Kuia Estate Cacao Farm in coastal Lahaina offer fascinating farm tours, along with delectable products and sweeping views.
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, tasting, 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 longtime spiritual site.
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