No pictures or words or VR experiences can prepare you for Hawaii, because one of the coolest things about a Hawaiian vacation is that it can be just about whatever you want it to be. You can make it anything from luxurious to down-to-earth, raucous to mellow, backcountry to metropolitan – and every one of those vacations can be the best trip of your life.
A lot of the differences in Hawaiian vacations stem from the islands you visit. Here’s a quick profile of each of the islands, knowing you can mix-and-match island adventures to your heart’s content.
The hardest thing for Hawaiian newbies to grasp is that the state has an island called Hawaii, but it’s not the most popular island, and it’s not where Honolulu is, even though the address may say “Honolulu, Hawaii.”
The island of Hawaii a/k/a The Big Island is the largest of the Hawaiian islands, and like Molokai, it’s a place to discover the “old Hawaii” – what the islands were like when the only way to get there was to hop the S.S. Lurline out of San Francisco.
The Big Island divides itself neatly into two sectors: Kona and Hilo. Kona, to the west, is sunnier and more volcanic – think coffee plantations and black-sand beaches – while Hilo is more tropical (though Hawaii Volcanoes National Park is just a half-hour from Hilo proper).
Full-on luxury options are harder to come by on Hawaii compared to some of the more developed islands, though the Mauna Lani Auberge Resorts balance luxury with respect for Hawaiian culture.
Regardless of where you stay on The Big Island, you come away understanding why the state is called Hawaii and not Oahu. It’s all there.
Kauai is surprisingly wild and rural, with most of the development concentrated in a few spots. Hawaii’s oldest and most northern island, Kauai also offers a wild climactic range from super-dry coasts to very wet and tropical mountains – all within a span of a few miles.
Such a diverse ecosystem is fragile by definition, so it’s important to know where you can and can’t go. As a result, while you can DIY and hike the floor of Waimea Canyon or take the Wai Koa Loop Trail through North America’s largest Mahogany forest, Kauai is better with an experienced guide like Hike Kaua’i With Me. Sure, you can take an aerial tour and be blown away, but Hawaii is so much better on the ground. And if you only have one shot at Kauai, why take chances?
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A private island mostly owned by Larry Ellison of Oracle fame, Lanai is home to the luxurious Four Seasons Resort Lanai and a whole lot of natural beauty, and that’s about it.
Though the luxury and scenery are great, the Four Seasons is wonderful, and there’s a cat sanctuary (!) -- Lanai is expensive, and exclusive, and beautiful – the area around Pu’u Pehe in particular. And if what you want from Hawaii is expensive exclusivity or exclusive expensiveness, this is your place. And the cat sanctuary is pretty cool.
Humpback whales have it right: they summer in Alaska and spend their winters off the coast of Maui.
Nothing fools these whales, for Maui is perhaps the most luxurious of the Hawaiian islands, without sacrificing any of the breathtaking beauty that makes Hawaii such a bucket-list destination.
All the big names in luxury resort accommodations are here, like the Four Seasons and the Waldorf Astoria, but when in Maui do as the Maui veterans do and opt for the low-rise Napili Kai Resort, which has been delighting visitors for 60 years with its authentic mid-century vibe.
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Often thought of as the agricultural island in the chain, Molokai is where cowboys (“paniolo”) once rode and island staples like corn and papaya are still grown and harvested the old-fashioned way.
Slow and sedate by design, Molokai nonetheless has spots of amazing beauty, such as the 3,000-foot-tall ocean cliffs that lead down to the national historic site of Kalaupapa, a former leper colony made famous by the legendary war correspondent Ernie Pyle.
Molokai is also known for being the island that most closely reflects the spirit and lifestyle of old Hawaii. As a result, it’s not a place for lovers of glitz, nightlife, surfing, or many of the other trappings of a Hawaiian vacation. But if you’re looking for peace and beauty, Molokai’s your jam.
What’s in Oahu? Just Honolulu, that’s all. And Waikiki Beach. And Diamond Head. And lots and lots of people, tourists and non-tourists alike.
For better and worse, Oahu is metropolitan Hawaii. The better includes iconic hotels like the Beachcomber and the Halekulani, Pearl Harbor, and Waikiki Beach and the view of Diamond Head from there. Better also means more restaurants, bars, and coffee shops, if those are must-haves no matter where you are.
The worse is the development and the amount of people. It’s like Miami Beach 20 years in the future, with pineapple shirts.
The good news is it’s not hard to leave behind the metro-ness of Honolulu. Just head to the North Shore and watch the surfers catch a wave like something out of Endless Summer, or simply climb the trail up to Diamond Head State Monument.
An Oahu vacation can be as chill as you like. Once you’ve had your fill of Honolulu, simply start wandering.
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The islands you can’t visit
There are eight islands in the Hawaii Archipelago. Visitors are banned from the smallest two, Niihau and Kaho’olawe.
Even though Hawaii is a domestic destination (no passport needed for Americans), trips there can be expensive, and need to be protected. Generali Travel Insurance has plans to help protect your dream Hawaiian vacation – and you can see for yourself by getting a quote. It’s fast and easy.