How To Plan A Hawaii Vacation For Family

Planning a Hawaii vacation for family can be one of the most enjoyable, amazing experiences of your life, especially if you do it the right way. You will want to get it all right from the start. Hawaii is a beautiful place and everyone can enjoy such a vacation. The most important aspect of any successful trip however is proper planning. This includes everything from travel safety, to budgeting, to lodging and activities. Here are some tips for planning your next Hawaii vacation.

When visiting Hawaii for the first time, it’s great to have an idea of what you would like to see and do. Of course, the big thing most people want to experience is a Hawaiian luau. But beyond that, it can get a bit overwhelming when determining all of the activities you should enjoy. However, if you plan your holiday around these three essential things: 1. beaches 2. water activities 3. culture Planning for a vacation to Hawaii may seem like a complicated process, but it’s not. Think about the most important thing when planning a trip.

How To Plan A Hawaii Vacation For Family

The Hawaiian Islands and its surrounding islets function as the 50th state of the United States of America in the Pacific Ocean. Out of the eight major islands, Oahu is the biggest and most populous island, accounting for more than one-fifth of the state’s population.

Critical Things to Know BEFORE Planning a Hawaii Trip

March 25, 2022 by Marcie Cheung

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Are you planning your first Hawaii vacation and want some helpful Hawaii travel tips? Find out things that no one tells you before planning a Hawaii trip!
This post about planning a Hawaii trip was originally posted December 25, 2020 and was updated January 13, 2022 and contains affiliate links which means if you purchase something from one of my affiliate links, I may earn a small commission that goes back into maintaining this blog.

I’ve been going to Hawaii for vacations since I was a kid. I know how lucky I was to have so many opportunities to explore the Hawaiian islands.

But because I’ve been going for the past 25 years, there are a lot of Hawaii travel tips that I’ve picked up along the way while traveling all the Hawaiian islands.

In fact, I didn’t even realize most of these were things the average tourist didn’t already know before going on their Hawaii trips.

So, I figured I’d break down the most crucial things I think travelers should know before planning a Hawaii vacation (and dispel a few rumors in the process!)

Keep scrolling to take a look at how to plan a trip to Hawaii like a pro!

Want to skip all the planning and just access my detailed Hawaii Itineraries complete with daily schedules, kid-friendly activities, and travel hacks? Click the button below.

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FAQ about How to Plan a Hawaiian Vacation

What is the best way to plan a trip to Hawaii?

You’ll want to think about the point of your trip. Is it to see specific attractions, experience Hawaiian culture, do a lot of water activities, go hiking, or just to relax? That will help you figure out which island(s) to visit. Then, you’ll want to check airfare for your desired dates and book your accommodation.

What’s the cheapest way to plan a trip to Hawaii?

The best way to see Hawaii on a budget is to visit during the off-season (the cheapest time being in September.) That’s when airfare and hotel stays are the cheapest and you can usually find the best Hawaii packages. You can also look into budget vacation rentals. And then fill your itinerary with free things to do in Hawaii like outdoor entertainment, hiking, swimming, going for walks, and relaxing at the beach.

How many days are enough in Hawaii?

While you might never want to leave Hawaii, usually people plan to stay 7-10 days during their vacation to Hawaii. That gives enough time to get over jet lag, participate in a few scheduled activities, explore the Hawaiian island a bit, and have time to relax and unwind.

What to Know Before Planning a Hawaii Trip

1. You Can’t Drive Between the Hawaii Islands

One of the top things people ask me is “Can you drive island to island in Hawaii?”

The answer is a simple no. The islands are much too far apart to drive and there are no bridges between islands in Hawaii.

There also isn’t a statewide ferry. There was the Super Ferry many years ago that was short-lived. Additionally, there used to be a ferry to Molokai, but that’s no longer running. Right now, there’s only the Lanai ferry from Maui, but it’s just for people.

Island hopping in Hawaii is a great way to see more than one island. Image of someone holding a hibiscus flower in front of an airplane window.
You’ll need to fly between most Hawaiian islands.

So, if you want to travel between islands 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. It’s the easiest way to see more than one island.

2. Avoid Golden Week

It’s really tricky to take vacations if you live in Japan. You have to request them really far in advance.

When planning trip to Hawaii, avoid Japan's Golden Week (end of April to early May.) Hawaii gets a ton of Japanese tourists that week and it's an expensive time to visit Hawaii. Image of a crowded Waikiki beach.
Waikiki Beach gets super crowded during Golden Week.

But, there’s a thing called Golden Week where people in Japan have 4 holidays off from work. That makes it a very popular time to plan a Hawaiian vacation. That’s because it’s the shortest flight to get to the United States from Japan.

Golden Week happens at the end of April and early May (in 2022, it’s 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 Oahu) because it will be tricky to find hotel rooms, beaches will be crowded, and you might not get to do all the tours or attractions you want.

Plus, the prices of hotel rooms seem to skyrocket for vacations to Hawaii that week. Do yourself a favor and check the dates before you book to save yourself some money.

3. Save Money with Companion Fares

The flights to Hawaii can be really expensive from anywhere on the Mainland, even if you travel during shoulder season (mid-April to June and September to mid-December).

One of my biggest Hawaii tips for saving money is to get an Alaska Airlines credit card. It comes with the Alaska Airlines companion fare, which is basically a BOGO deal for plane tickets. Well, you’ll pay full price for the first ticket and then just $99 for the second ticket.

My husband and I each have a card and we’re able to get our airplane tickets to Hawaii for half price because of it.

Alaska Airlines has a ton of direct flights to all the main 4 Hawaiian islands and they offer competitive rates.

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.

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