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Top 7 Island-Hopping Mistakes That Every Family Should Avoid in Hawaii

Are you thinking about island hopping in Hawaii but aren’t sure how to go about it? Scroll to find out the biggest Hawaii island hopping mistakes families make and how you can avoid them like a pro!
This post on Hawaii island hopping mistakes was written by Hawaii travel expert Marcie Cheung 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.

Island hopping in Hawaii sounds like a dream vacation, right?

Picture jumping from one stunning island to another, each with its own unique charm and adventures.

As someone who’s visited Hawaii over 40 times, I’ve got quite a bit of experience with island hopping.

But let me tell you, it’s not always as seamless as it sounds.

I’ve learned from plenty of mistakes along the way, and I’m here to help you navigate your island-hopping adventure so you can make the most out of your Hawaiian getaway without the typical missteps.

The 7 Worst Mistakes Families Make While Island Hopping in Hawaii

Mistake #1: Trying to Visit Too Many Islands

The Problem

When you first look at a map of Hawaii, it’s tempting to want to see every island. However, trying to squeeze too many islands into one trip can leave you and your family feeling rushed and exhausted rather than relaxed and refreshed.

How to Avoid It

Choose two, maybe three islands at most for your trip, depending on how long you’re staying. Each island has enough to keep you enchanted for days.

Taking your time allows you to explore more deeply and enjoy each island’s unique vibe without the stress of constant packing and moving.

Here are my tips for choosing the best Hawaiian island for your family. I’ve also got some great posts about Maui vs Oahu, Big Island vs Kauai, Maui vs Kauai, and Oahu vs Kauai.

Mistake #2: Underestimating Travel Time Between Islands

The Problem

It’s easy to think that flying between islands is quick and straightforward.

While the flights themselves might be short, the process of getting to the airport, going through security, and then getting from the airport to your accommodations can eat up a good chunk of your day.

Image of Marcie Cheung at the Maui Airport
I spent about 3 hours waiting here for my delayed flight from Maui to Kauai. Photo credit: Marcie Cheung

How to Avoid It

When planning your itinerary, consider travel days as lighter days in terms of activities.

Allow for half a day of travel when flying from one island to another. This way, you won’t be overbooked and can handle unexpected delays more smoothly.

Mistake #3: Overlooking Inter-Island Travel Costs

The Problem

Flights between islands add up quickly, especially for a family. If not planned carefully, you could end up blowing a significant portion of your vacation budget on just getting from one place to another.

Inter-island flights are nearly as cheap as they used to be!

How to Avoid It

Book your inter-island flights early to catch the best fares. Keep an eye out for special promotions and consider whether alternative modes of transport, like ferries, could offer a more scenic and cost-effective option for nearby islands like Maui to Lanai.

Mistake #4: Not Packing Appropriately for Island Transfers

The Problem

Moving between islands can mean varying climates and activities. Packing without considering these variations might leave you unprepared for rain in Hilo or chillier evenings on Haleakala.

I’m SO glad we had a rain jacket in our carry on when we landed in Hilo! Photo credit: Marcie Cheung

How to Avoid It

Pack layers and versatile clothing that can easily adapt to different weather conditions. Also, pack a day bag with essentials (like sunscreen, extra clothes, and snacks) that you can grab quickly without having to unpack your entire suitcase.

Mistake #5: Missing Out on Island-Specific Reservations

The Problem

Each Hawaiian island offers unique experiences that often require reservations, like visiting the Na Pali Coast on Kauai or watching the sunrise at Haleakalā on Maui.

Families sometimes arrive only to find out that these cannot be booked at the last minute.

We booked a Haleakala sunrise tour because we missed getting a reservation. Photo credit: Marcie Cheung

How to Avoid It

Research must-do activities for each island you plan to visit and book these experiences well in advance. Some activities, like the Haleakalā sunrise, require reservations months ahead, so plan accordingly to avoid disappointment.

Mistake #6: Not Packing Snacks

The Problem

A lot of people plan on getting food at the airport. But some airports have very limited food options. And those food options are EXPENSIVE. Plus, sometimes nothing is open if your flight is in the morning or evening.

Image of a sandwich, chips, and a drink at the Maui airport
This was my $25 lunch at the Kahului airport on Maui! Photo credit: Marcie Cheung

How to Avoid It

Grab local food to take with you to the airport. 7-Eleven in Hawaii has the best grab-and-go items for a great price. We like getting an assortment of musubi to keep our tummies happy while we wait.

Mistake #7: Failing to Adjust to “Island Time”

The Problem

The laid-back, relaxed pace of life, known locally as “Island Time,” can be a big adjustment, especially if you’re used to a fast-paced lifestyle.

Families often find themselves either frustrated by the slower pace or exhausting themselves trying to speed up their vacation.

How to Avoid It

Embrace the relaxed nature of the islands. Allow for flexibility in your schedule and take things slower.

This adjustment in mindset can help you truly enjoy the restorative nature of your vacation, giving you quality time to reconnect with your family.

Wrapping It Up

Island hopping in Hawaii with your family can be an incredible experience filled with adventure, relaxation, and unforgettable memories.

By learning from common mistakes and planning thoughtfully, you can ensure that your vacation is not just enjoyable but also smooth and stress-free.

Remember, the beauty of Hawaii isn’t just in its landscapes but also in its pace and way of life. Slow down and enjoy the ride.

Looking for more Hawaii island hopping resources? Check out Everything You Need to Know About Hawaii Island Hopping, Guide to Lihue Airport on Kauai, How to Get from Honolulu Airport to Waikiki Easily + Hassle-Free, and Honolulu Airport Tips!