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. And what is the best island to stay in Hawaii with family? The good news is, you can pick several! 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 for inter island travel. Hawaii vacations are all about finding your perfect pairings.
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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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. In the southern portion of the island is Wailea, known for luxurious crescent-shaped beaches and fabulous golf courses. In this region, we love booking clients for a stay at the Fairmont Kea Lani. It’s the island’s only all-suite and villa luxury resort and we can offer exclusive perks at this 5-star property.
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.
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. If Disney isn’t your cup of tea, Turtle Bay Resort, the Kahala Hotel & Resort, and the Four Seasons Resort Oahu at Ko Olina are all popular among our clients and staff. Because we know these properties first-hand, we can help you compare options and see what might be the best fit for your family.
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.
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 jaw-dropping 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.
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, be sure to get up to speed on current conditions before your trip. Mauna Lani, an Auberge resort, is a favorite luxury property here.
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!
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