How much time and effort you put into planning your trip has a direct effect on your Hawaii vacation. There are several factors that go into planning for Hawaii: deciding what to bring, choosing the best flights and rental cars, and even having a basic understanding of Hawaiian culture. Our blog post provides the information you need to know and will guide you through how to plan for your trip to Hawaii. 

What to bring 

This list may assist you in planning what to bring. Obviously, you won’t bring everything on the list, but it might make you think of a few things you may otherwise overlook:

Hiking shoes

For hikes on Maui’s Haleakala volcano, Kauai’s breathtaking Kalalau trail, and Oahu’s Diamond Head trail, you need sturdy hiking shoes to get the job done. The islands each have their own famous hiking trails, from the ones found in Big Island’s Hawaii Volcanoes National park to Oahu’s infamous Haiku stairs. Make sure you’re equipped with the appropriate gear to explore all of Hawaii’s stunning views. 

Hiking sticks

Carbon-tipped hiking sticks are best for any boulder-hopping hikes. In our guidebooks and app we have both an Activities and an Adventures section for any level of hiker. The Adventures section is full of experiences of a lifetime, but are for the serious adventurer. 

Hiking shoes for wet rocks

One of the activities in our Big Island Adventures chapter is to boulder hop to a waterfall. To see these falls, you’re gonna have to get wet and risk falling and breaking your ‘okole. Because although they’re only 900 feet from your car, you can’t see ’em, and there is no trail. You’ll have to get in the river and scramble upstream on big old boulders. And if you slip and fall, you probably can’t even use your cell phone to call for help, so be careful.  

Backpack with water bladder

Bring and drink lots of water when you are out and about, especially when you are hiking. Dehydration sneaks up on people. By the time you are thirsty, you’re already dehydrated. It’s a good idea to keep lots of water in your car. Our weather is almost certainly different than what you left behind, and you will probably find yourself thirstier than usual. Personal hydration packs (such as CamelBak) are great for hiking and going to the beach. 

Reef-safe water-resistant sunscreen

The hazard that by far affects the most people (excluding the accommodations tax) is the sun. If you want to enjoy your entire vacation, make sure that you wear a strong sunscreen. We recommend a water-resistant sunscreen with an SPF of at least 30. Apply 30 minutes before exposure for the most effectiveness. Physical sunblocks (those containing zinc or titanium oxide) are said to be more reef-safe than chemical sunblocks, which are more common.

Mask snorkel and fin set

Snorkeling gear can be rented just about anywhere. If you’re going to snorkel more than once, it’s nice to rent it for the week and keep it in your car so you can head to the water any time your little heart desires. If you want to buy your own, the cheapest prices will be at the Walmart/Sam’s Club Superblock outside of Waikiki on Keeaumoku. Also consider Costco if you’re a member.

Waterproof phone pouch

Keep your phone safe with a waterproof phone pouch. These pouches are a good purchase if you’re planning on doing any water activities such as kayaking. 

Mosquito repellent

A good mosquito repellent containing at least 10 percent DEET will come in handy, especially if you plan to go hiking. Forget the guidebooks that tell you to take vitamin B12 to keep mosquitoes away; it just gives the little critters a healthier diet. If you find one dive-bombing you at night in your room, turn on your overhead fan to help keep them away.

More items to bring:

  • Two bathing suits
  • Shoes—flip-flops, trashable sneakers
  • Shorts and other cool clothing
  • Camera with lots of storage
  • Light rain jacket and sweatshirt or light coat for some occasions.
  • Junk clothes for bikes, hiking, etc.
  • Cheap, simple backpack—handy even if you’re not backpacking
  • Hat or cap for sun protection

How to choose your flight

When planning your trip, a travel agent can be helpful, though that method is becoming less and less common. The Internet has sites such as Orbitz, Expedia, Cheap-tickets, Cheapair, Pandaonline, Priceline, Travelocity, Kayak, etc. If you don’t want to or can’t go through these sources, there are large wholesalers that can get you airfare, hotel and a rental car, often cheaper than you can get airfare on your own. Pleasant Holidays provides complete package tours.

Oahu

All passengers arriving on O‘ahu land at Honolulu International Airport. If you’re going to any of the neighbor islands, interisland flights are done by Hawaiian and Mokulele.

Big Island

Flight schedules change all the time, but United and others often have direct flights to Kona from the mainland. Not having to cool your heels while changing planes on O‘ahu is a big plus because interisland flights aren’t quite as simple and painless as they used to be. 

Maui

Though most visitors fly into Honolulu before arriving, there are plenty of direct flights to Kahului. 

If you’re staying in West Maui, it’s tempting to look at a map and decide to fly into Kapalua West Maui Airport for the sake of convenience. Though it is nearby, we still recommend flying into Kahului. That’s because the drive around the coastline into Lahaina during the day is dramatic and worth the extra time. It’s during your drive along the coastline to either west or south Maui that you realize that this island, more than any other Hawaiian island, has an extremely intimate relationship with the water. No other Hawaiian island has highways that embrace the ocean so much.

Kauai

Though most visitors fly into Honolulu before arriving, there are some direct flights to Kaua‘i. If you fly to Kaua‘i from Honolulu, the best views are usually on the left side (seats with an “A”). 

How to choose a rental car company

Oahu

O‘ahu is the only major Hawaiian island where a sizeable number of visitors stay without renting a car. Waikiki is small and walkable, and many activity companies will shuttle you to their locations, usually for an added fee. Plus, Uber and Lyft now both have a large enough presence on O‘ahu that you can rely on them to get a ride when you need it, at least around Waikiki and Honolulu, that is. 

Big Island

Rental car prices in Hawai‘i can be (but aren’t always) cheaper than almost anywhere else in the country, and the competition is ferocious. Nearly every visitor to the Big Island gets around in a rental car, and for good reason—it’s a big island. Fortunately, none have mileage charges. At Kona Airport, rental cars are a shuttle bus ride away. 

Maui

Maui prices fluctuate more than the other islands. Cheap at times, crazy high at others. Expect to pay an extra $10 or so per day in fees to pay for the new rental car facility and other goodies the government wants to charge you for. This seems like a good place to mention Uber and Lyft both have a presence on the island.

Kauai

The towns in Kaua‘i are separated by distances sufficient to discourage walking. Many of Kaua‘i’s best sights can only be reached if you have independent transportation.

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At Lihu‘e Airport, rental cars can easily be obtained from the booths across the street from the main terminal.

Hawaii weather

One of the biggest worries people have when planning their trip to the tropics is Hawaii’s weather. Will it rain? Is it going to be too hot? What about hurricanes? 

Our weather page on our website gives you a general overview of what to expect weather-wise on each island. With knowledge of Hawaii’s weather, you can make your trip to paradise unforgettable. 

Cultural notes

All land and water are considered sacred to native Hawaiians. To condense an elaborate and ancient paradigm, all parts of the environment, from people to rocks, are interrelated. Any harm that comes to one area will be felt in all others. Remember…you’re a guest, treat your time here like you’re a guest in someone’s house, (Imagine if you had four million people visiting your house. You’d want them to wipe their feet and clean up after themselves, right?)

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Don’t remove anything from the environment or cultural sites (heiau). This could be rocks, seashells, sacred offerings, plants and even sand (apart from what sticks to your feet and ‘okole after sitting on the beach). While it is tempting to take home a souvenir, it’s very disrespectful and ultimately damaging. Appreciate the setting, and take only pictures and memories.

Don’t try to imitate local dialects unless invited to. (Usually for resident’s amusement, because a visitor trying to speak pidgin sounds exactly like…a visitor trying to speak pidgin.)

Be a courteous driver. Plan ahead and leave extra time to get where you’re going. Morning, afternoon and lunch rush hour can be mind numbingly slow. Don’t honk your horn. It’s something that people in Hawai‘i just don’t do very much, unless it’s absolutely necessary. Take the opportunity to look around and enjoy where you are. You’ll get there eventually, so leave the road rage on the mainland. Don’t be in a hurry to get there—you are there. If you see something interesting, pull over to the side of the road (when safe) to investigate. Or just to let the faster drivers go around you, because you’re not in a hurry.

If invited into someone’s home, take off your shoes at the door, before you enter. You’ll most likely see a pile of flip-flops outside the front door of every house you visit. This is where they go. This Asian custom is the norm across Hawai‘i and nothing will annoy a local resident more than wearing your slippahs inside their house.

If in doubt, ask someone what the proper way to go about something is. If it is ordering from a local restaurant or about access to a waterfall, most locals are happy to help if you just ask.

Hawaii Itineraries

If you’re looking for more in-depth itineraries for your stay in Hawaii, including where to stay, what to eat and what to do, you can check out our island-specific trip guides here:

Oahu Itinerary

Big Island Itinerary

Maui Itinerary

Kauai Itinerary

To help you plan your trip even more, check out our new Hawaii Revealed app with everything you need to know about where to stay, including unbiased reviews, restaurants, and activities. Download the app for free on iOS to get previews of the best-selling Hawaii travel guides in the palm of your hand. Choose in-app purchases for full access to details on each island.

Download Hawaii Revealed App – iOS App or Android App\

Hawaii Revealed App

Download Hawaii Revealed App – iOS App or Android App

More things to reveal in the app:

  • Reviews on Hawaii Resorts with their locations
  • Reviews on every single beach on the islands
  • Interactive maps of Kauai, Maui, Oahu and the Big Island
  • Details to help plan your visit to Hawaii’s best sights, tours, activities and more
Download Hawaii Revealed App – iOS App or Android App

Download our app to find everything you need to know about the best island to visit in Hawaii