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The Hawaii Planning Guide Every Mom Needs: When to Book Everything from Flights to Fun

Are you thinking about going to Hawaii this year? Find out exactly what you need to do to plan your perfect Hawaiian vacation!
This Hawaii planning guide was written by Hawaii 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.

Planning a trip to Hawaii can seem like a daunting task, especially when you’re trying to juggle the schedules of a busy family.

As a seasoned traveler to the Hawaiian Islands, with over 40 visits under my belt, I’ve learned a thing or two about optimizing travel plans.

Whether you’re aiming for a summer vacation, squeezing in a trip during the school breaks, or looking for the calm of the off-season, this guide will help you nail down the perfect timing for everything from flights to fun activities.

Photo credit: Rojeena with Flytographer

1. Booking Your Flights: Timing is Everything

Ideal Booking Window

Aim to book your flights about 3 to 6 months in advance. For peak seasons, such as summer and winter holidays (especially around Christmas and New Year’s), getting your tickets as early as 6 months ahead can help you snag the best prices and preferred seating.

Photo credit: Marcie Cheung

For off-peak times, such as late spring (late April to early June) or fall (September to early November), you can afford to wait a bit longer, as airlines often offer deals about 3 months prior to encourage travel during these slower periods.

Last-Minute Deals

Sometimes, last-minute deals pop up within a month of departure, especially during the very end of the off-peak seasons. However, with kids in tow, it’s better to have plans locked in earlier to avoid the stress of uncertainty.

2. Securing Accommodations: Where to Stay

Booking Timeline

Hotels and vacation rentals should generally be booked around the same time as flights, especially if you are traveling during high season or want to stay at a particularly popular spot.

Photo credit: Marcie Cheung

The best properties get snapped up quickly for peak times, so early booking ensures you won’t miss out on your first choice.

  • For Summer and Winter: Book at least 5 months in advance.
  • For Shoulder Seasons: 3-4 months in advance is sufficient.

Types of Accommodations

Consider what will work best for your family. Resorts often offer kids’ clubs, pools, and more family-oriented activities, which can be a blessing when traveling with children.

Vacation rentals can offer more space and a kitchen, which helps save money on meals.

3. Planning Activities: What to Do

Hawaii is packed with activities, from snorkeling and hiking to cultural experiences like luaus.

Photo credit: Marcie Cheung

Booking these in advance can save you from the disappointment of sold-out experiences and long waiting times.

High-Season Activities

During peak tourist times, book popular activities like snorkeling tours or cultural shows like luaus at least 2 months in advance.

Here are the most popular snorkeling tours on Oahu, Maui, Kauai, and the Big Island.

These are our favorite luaus on Oahu, Maui, Kauai, and the Big Island.

You’ll also want to make reservations for things like sunrise at Haleakala (on Maui), the Haena Shuttle (on Kauai), and Diamond Head (on Oahu).

Off-Peak Flexibility

If you’re visiting during less busy months, you have more leeway. Booking a month in advance—or even once you arrive—might be perfectly fine.

However, for anything extremely popular or with limited availability, still consider booking as soon as your travel dates are set.

4. Car Rentals: Getting Around

Car rentals are essential for exploring the islands at your own pace. They can be surprisingly expensive in Hawaii, and prices often increase as availability decreases.

Image of the Budget car rental place in Kona
Photo credit: Marcie Cheung

Booking a Car

Try to book your car rental when you book your flight and lodging, especially if you travel during peak times.

This can also help you avoid the issue of rental shortages, which is a real problem during high seasons and particularly on less busy islands like Kauai or the Big Island.

The cheapest place I’ve found is Discount Hawaii Car Rental. They get the best rates from top national companies like Alamo, Dollar, Thrifty, Avis, Enterprise, Budget, and Payless. Check out the latest prices and more details.


Look into rental policies, as some companies have restrictions or high fees for additional drivers, which could affect your budget.

5. Dining Out: Where to Eat

While Hawaii offers incredible dining options, the best places can be busy, and waiting times can be long, especially with hungry kids.

Image of a boy with a hot dog in Waikiki
Photo credit: Marcie Cheung


If you’re visiting during a busy season, try to make reservations at least a month in advance for high-end restaurants or must-visit locations. For off-peak times, a week or so ahead of your visit might suffice.

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

Local Eats

Remember to explore local markets and smaller eateries. These don’t require reservations and can offer some of the most authentic and kid-friendly meals.

Here are some popular farmers markets on Oahu, Maui, Kauai, and the Big Island.

6. Packing for Hawaii

Remember, the weather in Hawaii is generally warm, but evenings can be cool, especially during the winter months.

Check out our packing lists for Maui, Kauai, and the Big Island.

Find out the best Kauai packing list for families by top Hawaii blog Hawaii Travel with Kids. Image of Open suitcase with clothes and personal things packed for traveling

During Hawaii’s rainy season, you might also want to bring a light rain jacket. And if you visit Haleakala Crater, Hawaii Volcanoes National Park, or Waimea Canyon, you’ll also want a sweatshirt.

Packing light layers that you can add or remove as needed is wise. Also, don’t forget essentials like sunscreen, hats, and comfortable walking shoes.

7. Leave Room for Spontaneity

While planning is key, especially with kids, Hawaii is a place of adventure and unexpected discoveries.

Leave some days open for spontaneous activities. Sometimes, the best memories are made when you stumble upon something unplanned.

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.

Hawaii Planning Guide Wrap-Up

With a little foresight and some strategic planning, your family can enjoy a seamless and magical Hawaiian vacation.

By booking at the optimal times for flights, accommodations, and activities, you’ll have the best trip yet!

Looking for more Hawaii tips? Check out Top Hawaii Questions Tourists Have Before Their First Trip to Hawaii, The Truth About Renting a Car in Hawaii: Mistakes You’re Making Now!, 7 Huge Mistakes Families Make at Hawaii Resorts and How to Avoid Them!, and Plan Your Hawaiian Vacation for Half the Price – Here’s How!