Hawaiian Island Hopping 101

No matter where you live, Hawaii is a long haul. While this tropical wonderland is worth every bit of time it takes to get there, it’s not surprising that people usually want to sample as much of the Aloha State as they can — the payoff for all those hours on a plane. That’s where island hopping comes in.

The four major isles (Maui, Oahu, Kauai and the Big Island) are well connected by air, so traveling between them is a snap. The harder part? Choosing which ones to visit. Use our guide to help narrow down the possibilities and find your perfect pairing.

Hawaiian Islands with Kids

Maui is the quintessential island for an introduction to Hawaii. Photo by Ernest von Rosen

Hawaiian Island Hopping Basics

If you’re a road warrior and want to hit as many highlights as possible, you can fit two islands into a week. Relaxation isn’t the goal here; you’ll be moving fast! To unwind and really dig into the local culture, or if you have very young kids who require naps and downtime, spend the full week on a single island. With 10 days to two weeks it becomes easier to add a second or even a third, bearing in mind that you’ll lose time in transit.

Fly open-jaw into one island and out of another to avoid backtracking. While the major airports throughout Hawaii tend to be pretty accessible, they’re a significant drive from some of the more unspoiled and beautiful areas. If you plan on island hopping, factor that in when deciding where to stay.

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Maui

What it offers: For most first-time Hawaii visitors, Maui tops the list. While it’s among the more touristed of the islands, it’s touristed for a reason: incredible natural beauty, reliably good weather, extensive activities, luxury resorts, idyllic beaches … the very things that make Hawaii such a draw. Maui has a number of distinct regions, from the luxe resorts and sunshine of West Maui to the hilly upcountry and the lusher, rainier eastern coast, that add up to an enticingly diverse experience.

What to pair with it: It’s easy to fill a week or more on Maui with a rich variety of adventures plus time to laze on the beach. But if you want to explore farther afield, take a short ferry ride to tiny, low-key Lanai. Pamper yourselves at the Four Seasons Lanai, one of our favorite luxury resorts in all Hawaii. Or fly to nearby Molokai for a couple of days — with a population of just 8,000, it’s extremely rural and has limited amenities and accommodations (one simple hotel and a handful of condo complexes). This is the place for families truly looking to unplug and get off the grid.

Hawaiian Islands with Kids

Families often plan a stay in Oahu just to visit Pearl Harbor. Photo by Nico Aguilera

Oahu

What it offers: People tend to think mainly of Honolulu, Waikiki, Diamond Head and Pearl Harbor when they picture Oahu, by far the most populous and developed of the islands. But there’s so much more to enjoy — starting with the beautiful North Shore, which has an old Hawaii feel and is famous for its excellent surfing. Near Honolulu, the laid-back Windward Coast offers some of the isle’s best scenery and panoramic views. Or escape to the western shore, home to Disney’s Aulani Resort, one of our favorite places to stay on Oahu with kids.

What to pair with it: While we don’t suggest Honolulu as a home base for an entire Oahu vacation, you could stay there a night or two to see a few major sights, then move on for a week elsewhere on the island or in a more relaxed destination like Kauai. As the region’s primary transit hub, Oahu is the easiest island from which to reach the others, so you’re spoiled for choice.

Hawaiian Islands with Kids

The unearthly beauty of the Na Pali coast is among the highlights of Kauai. Photo by Alex Schwab

Kauai

What it offers: Dubbed the Garden Isle, Kauai is the lushest and greenest of the Hawaiian islands. (It’s also the rainiest — you can’t have one without the other.) The drier South Shore, especially the upscale Poipu area, draws sun-seekers and families looking for calm, shallow water. It feels a world away from the wilder and more remote North Shore, home to rustic towns like Hanalei and the magnificent Na Pali Coast. Kauai’s appeal lies in adventure activities and jawdropping landscapes, not manicured luxury or a prime shopping and dining scene, so keep that in mind when deciding if it’s for you.

What to pair with it: Because most of this rugged island is inaccessible by road, it can take a while to get around. It’s ideal to stay a whole week, split between the North and South Shores. With two weeks, consider adding on the Big Island for a totally different landscape and atmosphere — the lava fields make an arresting contrast to Kauai’s rainforests and waterfalls — or Oahu for a hit of urban energy.

Hawaiian Islands with Kids

Black lava beaches dot the Big Island. Photo by Melinda Stuart

Big Island

What it offers: A relative newcomer as far as the Hawaiian islands go, the Big Island contains a staggering variety of landscapes, flora, fauna and microclimates. This is a place where you can goggle at black-sand beaches, lava fields, petroglyphs, coffee plantations, fierce kii statues and snowy mountain peaks all in the same week, not to mention take advantage of some of Hawaii’s best snorkeling and diving. Note, Kilauea Volcano’s 2018 eruptions have curtailed access to Hawaii Volcanoes National Park, and vog (volcanic smog) can sometimes pose a problem; click here for full information and updates.

What to pair with it: Given its size, this is the island that needs the most time to do it justice. In just a week, you’ll barely scratch the surface, though you can get a taste of the Kailua-Kona area on the west coast plus Hilo on the east. With more time, spend a full week in each of these, or build in a stay at the top-tier resorts on the Kohala Coast. If you’re determined to explore another island, consider Kauai or Oahu, which offer the most notable contrast.

Ready to embark on a Hawaiian adventure? Our Family Vacation Advisor team works with top-notch travel partners who provide amazing activities and bundle together value-added offerings such as flights. Give us a call to get started!

Relevant Links:

Browse all Hawaii travel tips and accommodations on Ciao Bambino

Why Hawaii is the ultimate tropical escape with kids

Best of Maui with kids: Sun and surf on Ka’anapali Beach

Splash! 5 favorite ocean adventures in Oahu

Kidding around Kauai: Why the Garden Isle is a dream for families

Go with the (lava) flow on Hawaii’s Kohala Coast

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