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Planning a Hawaii Trip: 14 Things to Know

Planning a Hawaii Trip: 14 Things to Know

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Are you planning a Hawaii trip for 2024 and have no idea where to start? Check out these 14 things to know before planning a trip to Hawaii!
This post about planning a Hawaii trip in 2024 was written by family travel expert Marcie Cheung and may contain affiliate links, which means if you click on the link and purchase the item, I will receive an affiliate commission at no extra cost to you. All opinions remain my own.

Are you planning your first Hawaii vacation?

I’m so excited for you! There are a lot of things that no one tells you before planning a Hawaii trip.

I’ve been going to Hawaii for vacations since I was a kid and there are some really important things that people need to know about before they go on their first trip.

So, let me break down the most crucial things I think travelers should know before planning their first Hawaii vacation.

You will learn about what it takes to plan a Hawaiian vacation from start to finish including flights, hotels, activities, and more.

And if you find this helpful or know someone else who would benefit from these suggestions too then please pass them along! It would mean the world to me. Thanks again and enjoy your time in paradise!

Want a Hawaii travel guide? I’ve got detailed guides and 7-day itineraries!

Hawaii Trip Planning FAQs

How do I start planning a trip to Hawaii?

First, you’ll want to figure out what time of year and how long you can stay. Then, you’ll want to pick which island(s) to visit and whether you want to stay in a condo or hotel. From there, you can make a list of activities and excursions and plan your trip to Hawaii that way.

How long should you plan a trip to Hawaii?

I always recommend at least 7-10 days for a Hawaii vacation. That gives enough time to adjust to the time difference and start to unwind and relax. And if you want to island-hop, I suggest at least 5-7 days per island.

What is the best time of year to go to Hawaii?

The cheapest time to visit Hawaii is during the shoulder season of mid-April to June and September to mid-December. If you want to see whales, you’ll need to visit in the winter. However, the most popular time to visit Hawaii is during the summer.

What to Know Before Planning a Hawaii Trip

1. You’ll Need to Fly Between Islands

If it’s your first time in Hawaii, you might be wondering “Can you drive island-to-island in Hawaii”? The answer is a resounding no!

Because of their distance from each other, it is not possible to drive between the islands in Hawaii.

Image of an airplane at Kona Airport on the Big Island of Hawaii.

There are also no bridges connecting them and only one ferry that serves as transportation for people going between Maui and Lanai.

So, if you want to visit more than one island during your vacation in Hawaii, you’ll need to island hop in Hawaii via airplane.

There are tons of inter-island flights each day between the Hawaiian islands. While the main hub is at the Honolulu International Airport, each island offers some inter-island flights.

This is definitely the easiest way to see more than one island on your trip to Hawaii.

2. Japan’s Golden Week Means Lots of Crowds in Hawaii

Japan is a country with some extremely strict travel/vacation regulations, but there’s one special time each year where these rules don’t apply: Golden Week.

Golden week happens at the end of April through early May and it’s when many Japanese holidays occur. That means people don’t have work and they are free to travel without using vacation days.

Image of a crowded Waikiki beach with Diamond Head in the background.

For 2022, Golden Week happens April 29-May 5. And Hawaii is flooded with Japanese tourists. This is not the best time to visit Hawaii.

I recommend avoiding Golden Week (especially if you’re heading to Waikiki) because it will be tricky to find hotel rooms at a decent price. Plus, beaches will be crowded and you might not get to do all the tours or attractions you want.

3. Take Advantage of Airline Companion Fares

Airfare to Hawaii can be crazy expensive.

Don’t let the high cost of flights from anywhere on the Mainland keep you away. Save money and time with an Alaska Airlines credit card!

You’ll get a companion fare for just $99 when purchasing your first ticket.

With many direct routes available to four major Hawaiian islands (Oahu, Kauai, Maui, and the Big Island) as well as competitive rates year round there’s no reason not to take advantage before prices go up again this summer.

We’ve flown almost all the airlines that go to Hawaii (we still need to try Southwest) and Alaska Airlines is by far our favorite. I think it’s the best way to visit Hawaii.

4. You Need Reef-Safe Sunscreen

Hawai’i is a place where they take their environmentalism seriously. That’s why all sunscreen sold in the islands must be reef safe.

Image of a woman putting on reef safe sunscreen in Hawaii while sitting on the beach in a black bikini.

You can check the ingredients on your current sunscreen to make sure it doesn’t contain any of the following:

  • Oxybenzone
  • Octinoxate
  • Octocrylene
  • Homosalate
  • 4-methylbenzylidene camphor
  • PABA
  • Parabens
  • Triclosan
  • Any nanoparticles or “nano-sized” zinc or titanium
  • Any form of microplastic

If you aren’t sure if your sunscreen is reef-safe, just wait to buy it in Hawaii. You can be assured that all sunscreen for sale in Hawaii is reef-safe. But, it’s usually more expensive to buy it at hotel gift shops. That’s why I suggest heading to Walmart or Target instead.

5. You’ll Probably Need a Rental Car

Unless you’re staying in Waikiki, renting a car is the best way to explore Hawaii. That’s because most tours and shuttles pick up from hotels around there so it’s easy for travelers like yourself who are traveling on their own accord- or with friends!

Image of someone driving a Jeep with the top off along a beach road in Hawaii.

The only exception would be if one rents bikes which can also serve as an alternative form of transportation depending on how much time they have available. But this will depend largely upon where each person wants to spend exploring during his/her trip.

And keep in mind that it does cost more to rent a car in Hawaii if you are under 25 years old. It’s best to book Hawaii rental cars well in advance to get the best price and availability.

The best place to rent a car in Hawaii is through Discount Hawaii Car Rental. They get amazing deals from top brands like Alamo, Thrifty, Avis, Budget, Dollar, Enterprise, and Payless. Check out the latest rental cars available and more details.

6. Hawaii Traffic Can Be Brutal

Hawaii is a dream destination for many people, but it can also be frustrating when you have trouble getting around due to the horrible traffic.

Image of traffic on a freeway on Oahu Hawaii

Consider where your activities will take place first and then plan on staying close by so that if there are any delays or accidents, they won’t affect plans too much!

Hawaii is also known for having a ton of year-round road construction. Keep an eye on traffic issues before you leave your hotel so you know which routes to avoid.

There have been a few times where we’ve been stuck in places where there’s just one highway and it’s totally thrown our plans.

Book a Family Photo Shoot

Whenever we travel, we almost always book a family photo shoot with Flytographer. They are super easy, affordable, AND guarantee that I’ll be in some photos. You can get $25 off if you book through this link or use the code HAWAIITRAVEL.

7. Schedule Spa Days Early in Your Trip

It’s easy to forget sun protection when you are on vacation. And when that happens, you’ll get sunburned. Ouch!

That can make massages and body scrubs extremely painful.

Image of orange tropical flowers, black stones, and a candle on a wooden background.

That’s why I suggest you do spa treatments early in the trip instead of booking them at the end.

You definitely don’t want to get treatments when your skin is so sensitive. Instead, kick off your trip with some spa time BEFORE you have a chance to get sunburned.

8. Set a Hawaii Budget

Hawaii is an island paradise. Unfortunately, this means that prices for food and accommodations can be sky-high compared to other places in the United States.

You'll definitely want to set a budget when planning a Hawaii trip with kids. Image of someone paying cash to another person.
man paying woman with dollars for the job

Simple groceries like bread or milk will give you sticker shock. And you’ll have to pay to park your rental car just about everywhere in Waikiki.

There are plenty of tips on how to save money while traveling through Hawaii but I think the most important thing to do is to create a realistic Hawaii travel budget. Be sure to include all activities, food, accommodations, and car rentals.

Most of our trips to Hawaii seem to have hidden costs we weren’t expecting, like park entrance fees.

9. Decide Between Staying in a Condo or Hotel

Think about where you want to stay on your next Hawaiian vacation. Not only do they have luxury resorts, but there are also tons of condos and vacation rental homes throughout the islands!

Image of a bunch of Waikiki hotels and buildings with the ocean and blue sky in the background.

The pros for staying in a condo vs hotel depend if cooking food or having separate bedrooms is important as well when deciding which type suits better with what kind of trip style. Both offer their own unique amenities depending upon preference.

But, hotels and luxury resorts can be super convenient for families. They usually have on-site restaurants, kid-friendly amenities, amazing pool areas, and sometimes even have a luau on the property.

10. You’ll Need to Bring Your Own Bags

When you go on vacation to Hawaii, it’s hard not having any plastic bags with which the purchase your items. That is because they banned them years ago!

So if you are planning a shopping trip (even at the grocery store), make sure to bring yours. Some gift shops may provide small paper ones but many won’t have that option either.

We always pack ourselves nylon foldable compact bags just in case though since these come in handy as a beach bag too.

11. You’ll Want More Than a Weekend

I remember being shocked years ago when my mother-in-law said they were heading to Hawaii “for the weekend.” It’s a 6-hour flight from Seattle and that seemed totally bonkers to me.

Image of a couple dressed up holding hands in Hawaii

Instead, I’d say that 10 days is the ideal amount of time to spend in Hawaii, especially if it’s your first time visiting Hawaii.

They say it can take some people a full week before they start relaxing on their vacation (instead of stressing about school/work).

Staying a shorter amount of time than that (especially for a first trip to Hawaii) will leave you feeling disappointed that you couldn’t stay longer.

12. Leave Room in Your Hawaii Itinerary

When you’re planning a trip to Hawaii, it is important that there’s enough time for everything on your list.

You’ll want the weather conditions in order and not have any plans change last minute- which means making sure they go as planned from start!

Image of a bunch of Hawaii maps, brochures, passports, camera, coffee and glasses as a flat lay image.

In our case, we typically leave 3 full days open near the end of our trip so if something comes up can always reschedule our planned activities. This helps in case they get rained out or something.

Those free days are also great for getting souvenirs, having a pool day, or doing something spontaneous.

You’ll never regret scheduling “free days” when planning a Hawaiian vacation.

13. Learn a Few Hawaiian Words

If you want to have a truly authentic experience while visiting Hawaii, be sure to take some time during your trip to learn some important words in the Hawaiian language. You will not regret it!

Image of the word Aloha spelled out with colorful chalk and a pineapple for the O

For example, the Hawaiian word for children is “keiki”. So you’ll want to ask for a keiki menu at restaurants if you’re traveling with kids. It also helps when you are figuring out the children’s rate for activities.

If you’ve seen Lilo & Stitch, you probably know the phrase “ohana means family.” The word “ohana” is used everywhere in Hawaii and that’s how most people will refer to your family.

The word “mahalo” is Hawaiian for thank you. Use this as much as possible! You can even say “mahalo nui loa” which means “thank you very much!”

Incorporating some Hawaiian words during your Hawaii vacations is a great way to learn a bit about Hawaiian history and culture, too. It’s also a great idea when traveling to Hawaii with kids.

14. You Won’t Get a Free Lei at the Airport

A lot of people visiting Hawaii for the first time have a notion that a hula dancer will walk up to them as they get off the plane and place a fresh flower lei on them.

Image of a bowl of fresh tropical flowers

I’ve been traveling here 25 years now but have yet seen anyone get one free at the airport – not even when they arrived back in their home state!

You can always book a lei greeting at the airport before your trip if you want to make it extra special. Or, ask about free (or paid) options when booking with hotels and resorts in advance!

How to Plan a Trip to Hawaii Wrap Up

Planning a trip to Hawaii can be daunting if you’ve never been before. But don’t worry, I’ve got you covered!

In this post, I shared my top tips for first-time visitors to the Aloha state.

If you want more information on how to plan a vacation to Hawaii, be sure to check out our other posts. We have tons of great content that will help make your trip planning easier and ensure that you have an amazing time in Hawaii.

Mahalo for reading and we hope to see you soon in the islands!

Looking for more Hawaii travel resources? Find out how to book affordable family photos in Hawaii, how to choose the best Hawaiian island, and my Hawaii with toddlers guide.

Want a Hawaii travel guide? I’ve got detailed guides and 7-day itineraries!

Looking for more Hawaii travel resources? Find out the best Hawaiian island for kids, how to plan a trip to Hawaii with toddlers, best Maui luaus, 25 things to do on Oahu with kids, my guide to Maui with kids, 25 things to do on Maui with kids, what to do on Kauai with kids, 25 things to do on the Big Island, and my Oahu family guide.

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