Traveling to Hawaii: 15 Things I Wish I Knew

Traveling to Hawaii and wondering how to plan? Don’t worry, I’ve got you.

When I first started planning my trip to Hawaii, I thought I had a pretty good handle on what to expect.

After all, it’s a U.S. state. No passport needed, same currency, and technically not that far.

However, once I arrived, I realized just how much I hadn’t known, and how much better prepared I could have been.

Hawaii might be part of the United States, but it truly feels like its own unique world.

Here are 15 things I genuinely wish I’d known before traveling to Hawaii.

Traveling to Hawaii: 15 Things I Wish I Knew

Hawaii feels like another country – in the best way

Hawaii is part of the U.S. But everything about it, the culture, the pace, the landscapes, even the language, makes it feel like you’ve stepped into an entirely different world.

That sense of “elsewhere” is part of the magic for me.

The local traditions, music, and food carry their rhythm, and the islands have a deep and complex history that shapes daily life.

It’s more than just a beach vacation. It’s a whole cultural shift.

Traveling To Hawaii: Not All Islands Are The Same – Not Even Close

When you look up Hawaii travel information, it’s easy to think of the islands as one big tropical blob with interchangeable beaches.

But each of Hawaii’s islands has a distinct personality.

Choosing the right one (or two) for your trip can make a huge difference in how much you enjoy your time there.

The Big Island, officially called Hawai‘i, is known for its vast volcanic landscapes, dramatic coastlines, and stargazing.

It’s the largest island by far and home to Hawai‘i Volcanoes National Park.

O‘ahu, where Honolulu and Waikiki Beach are located, is the most urban island and full of things to do, from nightlife to surfing to visiting Pearl Harbor.

Maui is more laid-back and luxurious, perfect for a romantic escape or scenic drives like the famous Road to Hana.

Kaua‘i, nicknamed the Garden Isle, is lush, quiet, and ideal for hiking or simply soaking in the beauty of nature.

Then there’s Moloka‘i, which is far less touristy and offers a much deeper connection to local culture and history.

Still, it’s not for everyone, especially if you’re looking for luxury resorts.

Do your research and pick an island that works for you.

Great Hotels In Hawaii

Ohana Beach Retreat at the Surf and Racquet Club – has an amazing location.

The Kahala Hotel and Resort– offers a luxurious retreat.

Hotel Wailea, Relais & Châteaux is really beautiful

Timbers Kauai Ocean Club & Residences is truly stunning

The Weather Is Stunning – But Also Surprising

One of the most common misconceptions I had was thinking the weather would be uniformly sunny and perfect all the time.

And yes, the weather in Hawaii is generally beautiful, but it’s also incredibly varied.

Each island has multiple microclimates. You can leave a sunny beach and be in a rainforest an hour later.

On the Big Island, for instance, Hilo on the east side is known for being one of the rainiest cities in the U.S.

While the west side near Kona is sunny and dry most of the time.

On Kaua‘i, you might be enjoying a peaceful beach day when a sudden rain shower rolls through.

In winter, the North Shores of several islands (especially O‘ahu) are known for their giant waves and world-class surf, while summer tends to be hotter, drier, and calmer across the board.

It’s always a good idea to check the forecast for the specific part of the island you’ll be in, not just the island as a whole.

I got sick on the plane – and you might, too

Hawaii is farther than it looks on the map. Depending on where you’re flying from, you could be in the air for six to twelve hours.

If you’re prone to motion sickness, come prepared, bring medication, hydration tablets, ginger chews, or anything else that helps you feel settled.

And avoid heavy or unfamiliar foods before flying.

It’s one of those details people don’t talk about, but it can make or break your first day.

Remember that when you are traveling to Hawaii, it can be a long way.

Read my article How To Avoid Getting Sick On A Plane for more details.

Island Hopping Isn’t As Casual As It Sounds

Before my trip, I had this romantic vision of hopping from island to island like I was sailing through Greece. In reality, it’s more complicated.

Most of Hawaii’s islands are connected only by short flights, not ferries, and those flights can be expensive or delayed depending on weather conditions.

If you’re only visiting Hawaii for a week or so, I recommend sticking to one island and immersing yourself in it.

If you’re there for 10 days or more, you could potentially visit two, but be aware that travel time, check-ins, and logistics will eat into your relaxation hours.

I tried to squeeze in too much and ended up feeling rushed.

You’ll Probably Need A Rental Car – And They’re Not Always Easy To Get

Unless you’re staying in the heart of Waikiki and don’t plan on exploring much beyond Honolulu, a car is essential.

Hawaii’s best spots, like remote beaches, waterfall trails, and scenic landscapes, aren’t usually walkable or accessible by public transit.

What I didn’t realize is how competitive the rental car market can be, especially during peak season.

I’ve seen car rental prices spike to over $150 per day during busy times, and occasionally, there are actual shortages.

Book your rental car as early as possible, or explore peer-to-peer car-sharing apps like Turo if availability is limited.

Food Is Expensive, But The Flavors Are Unforgettable

I expected meals to cost a bit more on the islands, but I was still caught off guard by how quickly it added up, especially at sit-down restaurants.

That said, Hawaii’s food scene is worth exploring.

Some of the best bites I had came from roadside stands and local food trucks.

Don’t leave without trying a traditional Hawaiian plate lunch (typically a protein with rice and macaroni salad), fresh poke bowls, malasadas (Portuguese-style donuts).

And don’t forget shaved ice, especially from a small, local shop.

You can also find incredible Japanese, Korean, and Filipino food depending on the island you’re on.

Budget for food, but also make space to be adventurous. It’s part of the experience.

Book Tickets Here: Oahu: Chocolate Farm Tour with Tasting – Kamananui Cacao

Learn A Little About The Culture Before You Go

Hawaii isn’t just a vacation destination; it’s home to a living, breathing culture with deep roots.

The islands have a complex history, including colonization, the overthrow of the Hawaiian monarchy, and an ongoing movement for sovereignty and preservation of native identity.

That history is still very present today.

Taking the time to understand a bit about the culture, language, and local customs makes a real difference.

Learn a few Hawaiian words like aloha (hello/love) and mahalo (thank you), and always show respect at cultural or sacred sites.

Simple gestures go a long way and show that you’re not just a tourist, but a thoughtful guest.

Traveling To Hawaii Essentials Packing List I Wish I Knew About

Here are my tips on how to pack lightly when traveling to Hawaii.

This unisex RFID-blocking concealed travel pouch is lightweight and comes in several colors.

These RFID sleeves are another solution.

This Anker high-speed phone charging battery is the exact one I carry with me on all of my trips.

My daughter gifted me this FugeTek selfie stick and tripod setup for my birthday. It is made of lightweight aluminum and is so easy to use.

I never leave home on a trip without my Bobble filtration bottle. The 18.5-ounce size is perfect for exploring.

And the replacement carbon filter ensures fresh, clean water whenever you fill the Bobble.

Then this collapsible silicone foldable water bottle would also work well for you.

This foldable water-resistant backpack would be great for a daily go-pack.

These quick-dry slip-on Aqua shoes will be useful when heading to the beaches in Hawaii.

These men’s quick-dry trunks are essential.

For women, this one-strap one-piece bathing suit is amazing.

Consider bringing along quick-dry super-absorbent microfiber towels.

This wet-dry bag with handles is a good option.

These unisex polarized sunglasses come in many lens colors and frame designs and are extremely affordable, too.

If you like aviator-style sunglasses, these polarized aviators may interest you.

As an Amazon Affiliate, I earn from your qualifying purchases.

You Should Book Your Excursions In Advance

Some of the most popular activities in Hawaii sell out fast, especially anything involving sunrise, hiking permits, or boat tours.

I waited too long to book sunrise at Haleakalā in Maui and missed out. Lesson learned.

If you have your heart set on something like snorkeling at Molokini Crater, attending a traditional lūʻau, or going on a manta ray night dive, reserve it in advance.

Here are some suggestions to consider:

Ohau: Pearl Harbor, USS Arizona, and City Tour

South Maui: Molokini & Turtle Town Snorkeling Tour with Meal

Maui: Road To Hana Adventure with Breakfast & Lunch

Sunrise Is Often More Beautiful Than Sunset

I love a golden beach sunset as much as anyone, but Hawaii’s sunrises took my breath away.

On O‘ahu, hiking to Lanikai Pillbox for sunrise was one of the most magical travel moments of my life.

On Maui, sunrise over the clouds at Haleakalā is unforgettable.

If you’re an early riser (or willing to become one temporarily), make the effort to wake up early at least once.

The peace, the light, the hush over the landscape, it’s a side of Hawaii that many travelers miss.

Book Tickets Here: Hawaii’s GOAT Experience: Mauna Kea Summit, Sunset & Stars

Nature Is Stunning, But Also Powerful

The natural beauty of Hawaii is overwhelming. Waterfalls, cliffs, beaches, rainforests, it’s like walking through a dream.

But nature here is also something to be taken seriously. Riptides are common.

Flash floods can happen suddenly in canyons and trails.

Volcanic rock is sharp and can slice up your feet if you try to hike in flip-flops. Always wear closed-toe shoes.

Check trail conditions before you hike. Listen to local advice. Never turn your back on the ocean.

And please, don’t touch wildlife like sea turtles or monk seals. The best way to enjoy Hawaii’s natural beauty is to respect it.

Book Tickets Here: Kauai: Guided Hike and Waterfall Swim

Traveling To Hawaii: Travel Insurance Is A Smart Idea

After experiencing a weather delay that almost cost me a non-refundable hotel night, I’m a convert.

Flights between islands can be delayed due to rain or wind, and car rentals or activity bookings sometimes come with strict policies.

If you’re investing in a special trip to Hawaii, especially one with multiple moving parts, a little extra coverage goes a long way in protecting your plans (and your wallet).

Not All Sunscreen Is Allowed- Pack Reef-Safe

Hawaii has banned the sale of sunscreens containing oxybenzone and octinoxate because of the damage they cause to coral reefs.

That means you need to bring or buy reef-safe sunscreen made with mineral ingredients like zinc oxide or titanium dioxide.

This isn’t just a rule, it’s part of Hawaii’s effort to preserve its fragile marine ecosystems.

And honestly, mineral sunscreens are great for your skin anyway.

Reef-Safe Sunscreen

It’s Okay To Be A Tourist – Just Be A Respectful One

It’s easy to feel unsure of how to “do Hawaii right,” especially with growing awareness of over-tourism and cultural sensitivity.

You don’t need to overthink it. Just show up with respect.

Ask questions. Shop local. Support Hawaiian-owned businesses. Be curious and kind.

Enjoy your lūʻau, take your photos, wear your lei, but don’t trespass for a view, don’t climb sacred sites.

And don’t carve your name into anything. A little respect goes a long way.

Book Tickets Here: Kailua-Kona: Voyagers of the Pacific Luau with Buffet Dinner

Traveling To Hawaii: You Will Want To Return Before You’ve Even Left

I remember sitting on a quiet beach in Kaua‘i on the final morning of my trip, watching the light change over the water.

I was feeling like I was already homesick for a place I hadn’t left yet. That’s what Hawaii does to you.

One visit often turns into a lifelong love affair.

So if you’re planning your first trip, know this: it probably won’t be your last.