10 Tips to Maximize Your Trip to Hawaii

PHOTO: Aerial view of Hawaii's Lanikai Beach. (photo via segawa7/iStock/Getty Images Plus)
Will McGough
by Will McGough
Last updated: 8:00 PM ET, Sun September 29, 2019

Maximize Your Trip to Hawaii

Planning a trip to Hawaii can be overwhelming. It's far, it can be expensive, and there's a lot to consider, like which island(s) to visit and where to stay. While you figure out the specific details, here are ten big-picture tips to help you get the most from your trip to Hawaii.

Visit More than One Island

This might seem like common sense, but the truth is that many people only visit one island. It's a long trip no matter where you come from, so seeing more is a smart choice, but it goes beyond that. Each of the six major islands is so different from the others - drastically so - and to visit only one will leave you with a very narrow view of Hawaii. Oahu on its own is not Hawaii, neither is Maui or Kauai or Big Island. Only when you visit a handful to you start to get a feel for the chain as a whole. Visit at least one other, two or three more if possible!

Vary Where you Stay

Just like all the islands have their own personalities and landscapes, so too do the sections of each individual island. You'd be surprised how much difference there is between Kona and Hilo, for example, or Honolulu and Haleiwa. It might be convenient to stay in one place, but moving around gives you such different experiences that it's worth it in our book. Try a hotel for a few days, then maybe a bed and breakfast, and seek out locations that differ from one another.

Rent a Car

You can't do Hawaii properly without a car. Period. End of story. Local buses are slow, and outside of Honolulu, they don't run often enough to be efficient for a visitor (you'll waste way too much time in transit). Plus, without a car, you miss out on the scenic drives, and lose access to the raw, lesser-developed parts of Hawaii.

Aim for Shoulder Season

Though the kids are off in summer and the whales are around in winter, consider coming during the shoulder seasons, either spring or fall. Rates are cheaper, the weather is cool and stable, the number of visitors is generally lower, and the sunsets are still epic.

Visit Oahu First, and Go Beyond Waikiki

When planning the order of the islands you are going to visit, always put Oahu first. Because it's the most developed, you'll want to experience it before going to some of the less-developed islands. Reversing that course will make appreciating the city tough, because you will have gotten used to the mellow vibes of the outer islands. Hit the big city first, then carry on for some chill time.

And, don't forget the most important rule when you visit Oahu: Take a day or two or more to get out of Honolulu and Waikiki. Making the city your home base is understandable (excellent food!), but Oahu has so much more to offer. Its outdoor opportunities rival that of any outer island.

Leave Your Coconut Bra and Grass Skirt at Home

Sure, you might see these costumes worn during a luau, but that's a legit tribute to the past. Prancing around in one on the beach is another story, and represents a skewed view of Hawaiian culture. I mean this literally, for sure, but I also mean it symbolically. Hawaii is a changing place. In the 1970s, a cultural renaissance began in Hawaii, and it aims, in part, to break free from the stereotypes Hawaii has gathered over the decades (which were produced, in part, by its own tourism board back in the day). Before your trip, do some reading to educate yourself, and check to see if your hotel has a cultural ambassador.

Don't Skip Hawaiian History

Visit Pearl Harbor? For sure. But most don't go beyond that, which means they only get the U.S. history in Hawaii - not Hawaiian history itself. Some go to the Polynesian Cultural Center, which is a step in the right direction but doesn't exactly drive home the details of Hawaii's past. Carve out some time to visit the Bishop Museum, which is the state's premier museum for its history and culture. Look for smaller yet still impressive museums on other islands, like the Kauai Museum, for a look at its specific history. You can also visit cultural sites, like the Iolani Palce or the Heeia fishpond, to learn more about how the past is shaping the future.

Pack Less. Much Less.

I know, you need three pairs of shoes and a couple of outfits. But do you really? Hawaii is one of those places where you can truly get away with the most basic of attire, where simply wearing clothes at all gets you into 99.9% of establishments (you will no doubt see shirtless people at the grocery store). Use this as an opportunity to cut back on what you pack - light luggage makes you mobile, as it is much easier to island-hop, switch hotels, and survive in a small car. A couple of bathing suits, a pair of shorts and a couple of t-shirts gets the job done for men; a few casual dresses or cover-ups for the gals.

Plan Adventures at Night

Don't go inside after the sunset! Hawaii is one of the best places in the world to stargaze - as evidenced by the presence of many international telescopes - so don't miss out. Lay out on the beach away from the lights at night, or consider driving to a quiet lookout that would otherwise be busy during the day. Plan a night hike. Whichever way, take some time to recreate at night and bask under the bowl of stars. For those coming from cities on the mainland, the night sky is sure to surprise.

Check Permitting Rules

Because of a myriad of factors, mostly surrounding overtourism and rapid growth, lots of things have changed in recent years: Sunrise at Haleakala now requires an advanced reservation, for example, and the North Shore of Kauai has a brand new, strict permit system. While seemingly inconvenient, these new regulations are aimed at improving the quality of local life, which I think we can all get behind (see above link on the North Shore of Kauai). Check into local policies to ensure you don't show up empty-handed - and walk away disappointed - when a permit or reservation is required.

These 10 tips will help you get the most out of your trip.

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Helping leisure selling travel agents successfully manage their at-home business.

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Laurence Pinckney

Laurence Pinckney

CEO of Zenbiz Travel, LLC

About Me