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10 Insider Tips for Planning an Unforgettable Hawaii Family Adventure!

Dreaming of your first trip to Hawaii? Let me show you exactly how to plan a trip to Hawaii like a pro!
This post about how to plan a trip to Hawaii 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.

Are you daydreaming about swaying palm trees and stunning sunsets but dread the thought of planning a family trip to Hawaii?

You’re not alone.

Planning a vacation to a place you’ve never visited can feel like navigating a tropical maze without a map.

But don’t worry—I’m here to be your guide and make it easy and exciting instead of overwhelming!

I’ve visited Hawaii more than 40 times and I have a LOT of tips for planning your perfect trip!

👉 Do you prefer writing things down to plan? I’ve got a great Hawaii workbook that walks you through each step of planning your trip. It’s available on Amazon.

Your Ultimate Guide to Planning a Family Trip to Hawaii

Choosing the Right Island for Your Family

Deciding which island to visit is the first big step. Each Hawaiian island offers something unique:

  • Oahu: This island is a hub for historical sites like Pearl Harbor, fabulous shopping, and bustling nightlife. It’s perfect for families looking for a mix of adventure and culture.
  • Maui: Known for its scenic drives like the Road to Hana and luxurious beach resorts, Maui blends adventure with relaxation.
  • Kauai: If your family loves the outdoors, Kauai is ideal. Known as the “Garden Isle,” it offers lush landscapes and dramatic waterfalls.
  • Big Island: As its name suggests, it’s large and diverse, with everything from volcanic parks to black sand beaches.

Once you pick your paradise, you can dive into the fun part—planning your activities!

When to Visit Hawaii for the Best Experience and Deals

Timing is everything, especially when it comes to visiting Hawaii.

Fall is a wonderful time to visit Hawaii.

If you’re flexible, consider going during the shoulder seasons—mid-April to June or September to mid-December. You’ll enjoy beautiful weather, fewer crowds, and better rates on accommodations.

How Long Should You Stay?

To really soak in the Aloha spirit, I recommend staying at least 10 days. This gives you enough time to explore without feeling rushed, adjust to the time difference, and maybe even hop between islands if you’re feeling adventurous.

👉 I’ve got some great 7-day itineraries for Oahu, Maui, Kauai, and the Big Island and it’s easy to add in some pool/resort days.

Scoring the Best Airfare to Hawaii

Start monitoring flights early, especially if you’re flying from the East Coast. Keep an eye on deals and consider alerts from websites like Skyscanner or Google Flights.

Find out how to fly to Hawaii with kids without losing your mind with tips from top Hawaii travel blog Hawaii Travel with Kids. Image of a boy walking toward a plane in Hawaii
We’re lucky to have so many direct flights to/from Seattle! Photo credit: Marcie Cheung

And remember, sometimes a direct flight is worth the extra bucks for the convenience and shorter travel time.

What to Do in Hawaii: Creating Your Bucket List

Sit down with the family and make a list of everyone’s must-dos. Whether it’s snorkeling, hiking, or simply finding the best beach to relax, make sure there’s something for everyone.

Here’s a little secret: mix up busy activity days with relaxed days to keep everyone energized.

Finding Your Home Away from Home

Where you stay can make or break your vacation. If you’re planning lots of activities, choose accommodations nearby to minimize driving time.

👉 Here are our favorite kid-friendly resorts on Oahu, Maui, Kauai, and the Big Island.

My kids love resorts for their pools and shave ice! Photo credit: Marcie Cheung

Resorts offer lots of amenities but consider vacation rentals or condos for longer stays—they often come with kitchens, giving you the option to cook meals and save money.

The Ultimate Hawaii Itinerary: Keeping Everyone Happy

Don’t try to cram too much into each day. Hawaii is about experiencing the beauty and culture at a relaxed pace.

Plan major activities for the morning when everyone is fresh, and leave afternoons open for spontaneous adventures or downtime.

Car Rental: Exploring at Your Own Pace

Renting a car gives you the freedom to explore at your leisure and is almost essential for islands like Maui and the Big Island.

We ALWAYS rent a car in Hawaii because we like to explore at our own pace. Photo credit: Marcie Cheung

Book in advance to get the best rates and make sure you have a comfortable vehicle that fits the whole family and your luggage.

👉The best place to rent a car in Hawaii is through Discount Hawaii Car Rental. They get the best rates through national companies like Alamo, Enterprise, Budget, Dollar, Thrifty, Avis, and Payless. Check out the latest prices and more details.

Packing for Paradise

Pack light but don’t forget essentials like reef-safe sunscreen, hats, swimsuits, and comfortable walking shoes.

And here’s a pro tip: bring a reusable water bottle for each family member to stay hydrated and save money.

Enjoying the Journey

Finally, remember that planning a trip to Hawaii is part of the adventure. Involve the kids, make decisions together, and build excitement as your vacation approaches.

Hawaii offers an incredible mix of activities and relaxation, ensuring that every family member comes home with special memories.

Planning your family’s Hawaiian vacation doesn’t have to be stressful. With the right preparation, you can create a trip that’s as relaxing or as adventurous as you want it to be.

Start with these tips, jump into the details, and get ready to enjoy a slice of paradise. Aloha!

Looking for more Hawaii travel tips? Check out How to Survive Long Flights to Hawaii with Kids, Why Your Kids Might Hate Hawaii, and 10 Secrets No Travel Agency Will Tell You About Hawaii Family Vacations!