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The #1 Mistake Every Parent Makes When Booking a Hawaiian Vacation (And How to Avoid It)

Are you planning your first trip to Hawaii? Keep scrolling to find out the top Hawaii mistake parents make and what to do instead!
This post about Hawaii 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.

Planning your first family trip to Hawaii can feel like preparing for a journey to another world.

Between the vibrant culture, breathtaking landscapes, and the spirit of Aloha, the islands offer a unique adventure for families.

I’ll let you in on a secret: even with over 40 trips to Hawaii under my belt, each visit teaches me something new, especially when it comes to planning.

And yes, there’s one mistake I’ve seen (and made) time and again when booking a Hawaiian vacation.

Let’s dive in, so you don’t fall into the same trap.

Image of two boys at Kualoa Beach Park on Oahu
Photo credit: Natalie with Flytographer

The #1 Mistake: Overpacking Your Hawaii Itinerary

Hawaii is a dream destination with its lush landscapes, pristine beaches, and rich culture. It’s tempting to cram every recommended activity into your schedule.

I’ve been there, believing that more is better, trying to squeeze in every waterfall hike, snorkeling spot, and cultural experience into one trip.

But here’s the truth: the magic of Hawaii isn’t just in its attractions; it’s in the moments of unplanned adventure and relaxation.

The biggest mistake? Overbooking your days and missing out on the spontaneous joys that make Hawaii special.

Check out this honest Kohala Zipline tour review by top Hawaii blog Hawaii Travel with Kids! Image of a mom and son ziplining on the Big Island
My son and I always add ziplining to our Hawaii itinerary!

Here’s How to Avoid It

Prioritize and Pick

Sit down with your family and choose the top three must-do activities. Make these your vacation pillars, spreading them out over your stay.

For my kids, that usually involves ziplining, a luau, and an ATV ride.

This approach leaves room for rest, unexpected discoveries, and the simple pleasure of being together in paradise.

Embrace Local Life

Part of Hawaii’s charm is its laid-back lifestyle and warm community.

Instead of rushing from one tourist spot to another, take time to explore local markets, chat with residents, and maybe stumble upon a neighborhood beach.

These experiences often become the most cherished memories.

Balance Activity with Relaxation

For every adventure-packed day, plan a chill day. Whether it’s lounging on the beach, pool time at your hotel, or just enjoying a tropical treat on your lanai (balcony), downtime is essential.

As a total type-A planner, this has been the biggest shift I’ve had to make in planning family vacations to Hawaii.

Hawaii’s beauty is best appreciated at a leisurely pace, allowing everyone to recharge and reflect on their experiences.


Smarter Planning Tips from 40 Visits

Through my myriad of trips, I’ve gathered some wisdom on making the most of your Hawaiian vacation. Here are a few tips to help you plan smarter, not harder:

Accommodation Wisdom

Personally, my family LOVES Hawaii resorts and hotels and that’s usually where we stay.

But, you might want to think beyond the hotel. Resorts are fantastic, with their pools and direct beach access, but they can also be pricey and crowded.

Vacation rentals or condos can offer more space, kitchen facilities, and a cozy, home-like atmosphere. Plus, they’re often more budget-friendly, especially for larger families.

Car Rental Insights

Renting a car is almost a must in Hawaii, but here’s a tip: book as early as possible. Prices tend to soar as your travel dates approach.

We usually find the best deals with Discount Hawaii Car Rental. They partner with all the main rental car companies in Hawaii but offer a cheaper price.

Having a car gives you the freedom to explore at your own pace and discover hidden gems off the beaten path.

Pack Smart

Yes, Hawaii is warm, but it’s also diverse in climates. While beachwear is essential, don’t forget a light jacket for cooler evenings and sturdy shoes for hikers.

Also, reef-safe sunscreen is a must to protect both your skin and the delicate marine ecosystems.

We usually do family photoshoots in Hawaii, so I put all our “nice” clothes in a separate packing cube so they don’t get dirty.

Learn About Hawaiian Culture

Hawaii is rich in history and traditions. Take time before your trip to learn with your kids about the islands’ culture, language, and customs.

I’ve got a list of Hawaiian books for kids that will help them get excited for your trip AND learn a bit about what to expect.

It will make your visit more meaningful and show respect for the local way of life.

Timing is Everything

Lastly, consider the timing of your visit. Peak seasons mean crowded beaches and attractions, along with higher prices.

Visiting during the shoulder seasons (mid-April to June and September to November) can offer a more relaxed experience with the bonus of better deals.

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.

Top Hawaii Mistake Wrap-Up

Going on your first Hawaiian vacation with your family is an exciting venture. It’s a chance to create lifelong memories, immerse in new cultures, and enjoy nature’s unparalleled beauty.

The key to a successful trip lies not in doing everything but in savoring each moment, whether it’s marveling at a sunset, enjoying a local meal, or just being together in one of the most beautiful places on Earth.

Remember, Hawaii isn’t just a destination; it’s an experience.

By avoiding the common pitfall of overplanning and embracing a more relaxed approach, you’re set for a family vacation that’s as enriching as it is enjoyable.

And who knows? With these tips in mind, you might just find yourself coming back to the islands, again and again, each time discovering something new, just like I did.

Aloha and happy travels!

Looking for more Hawaii tips and tricks? Check out 25 Hawaii Mistakes Every Tourist Has Made, 105 Genius Tips for Hawaii on a Budget, 13 Tips for Visiting Hawaii for the First Time, and 17 Things You Will Probably Forget for Your Family Hawaii Packing List!