Home » Hawaii Travel Tips » 5 Mistakes Moms Make When Planning Their First Hawaiian Vacation (And How to Avoid Them)

5 Mistakes Moms Make When Planning Their First Hawaiian Vacation (And How to Avoid Them)

Are you heading to Hawaii this year but aren’t feeling confident? Find out how to visit Hawaii with kids (and what mistakes to avoid)!
This list of tips for visiting Hawaii with kids 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 family vacation to Hawaii is exciting! Imagine lounging on sun-soaked beaches, exploring lush rainforests, and experiencing vibrant local culture.

However, for first-timers, especially busy moms planning for the whole family, it’s easy to fall into some common traps that might put a damper on your tropical getaway.

As a mom of two boys with over 40 trips to Hawaii under my belt, I’ve seen it all and learned how to avoid these pitfalls.

Let’s explore the five common mistakes moms make when planning their first Hawaiian vacation—and how you can sidestep them for a flawless island escape!

Image of a grandma pushing a toddler in a stroller next to a preschooler and a mom in Hawaii

The Biggest Mistakes Moms Make When Planning a Hawaii Family Vacation

Underestimating Travel Time Between Islands

The Mistake

It’s tempting to think of hopping between the Hawaiian Islands as quick and easy. After all, flights can be as short as 25 minutes.

However, many forget to factor in the time needed to get to and from airports, security checks, and waiting for your flight. This can turn a simple inter-island hop into a half-day ordeal.

Find out how to go island hopping in Hawaii with tips from top Hawaii blog Hawaii Travel with Kids. Image of a Hawaiian Airlines airplane at Hilo Airport.

How to Avoid It:

  • Plan Ahead: When scheduling your flights between islands, consider the entire journey time, not just the flight. Add at least 2 hours to your schedule for airport processes and transit.
  • Limit Island Hopping: If possible, limit your trip to one or two islands, especially if your stay is short. This reduces travel stress and gives you more time to explore and relax. Here are the best islands for kids.
  • Early Flights: Opt for the first flights out in the morning to minimize delays and make the most of your day.

Overlooking Local Holidays and Festivals

The Mistake

Hawaii has a rich culture and hosts numerous festivals and public holidays that many aren’t aware of. Visiting during these times can lead to unexpected crowds and sold-out tours and activities.

How to Avoid It:

  • Research Before You Book: Look up Hawaii’s local holiday calendar and note any significant cultural festivals. These can be wonderful to experience but come with their own set of challenges like crowded venues and high prices.
  • Book Early: If your trip coincides with a major festival and you decide to join in the fun, make sure to book your accommodations and activities well in advance.
  • Local Insight: Check local blogs or contact your hotel in advance to ask about upcoming events during your stay.

Not Preparing for the Weather

The Mistake

With Hawaii’s eternal summer image, it’s easy to assume that the weather is always beach-perfect.

However, Hawaii has microclimates that can change unexpectedly, leading to rain or cooler temperatures, especially on higher elevations like Hawaii Volcanoes National Park or Haleakala Crater.

How to Avoid It:

  • Pack Accordingly: Include light rain jackets and layers for cooler areas. Waterproof gear is also a good idea if you plan on hiking in rainier spots like Hilo.
  • Check the Weather Daily: Hawaii’s weather can change quickly. Keep an eye on local forecasts, and plan your activities accordingly.
  • Flexibility: Have a backup plan for indoor or alternative activities in case of bad weather.

Neglecting to Budget for Extras

The Mistake

It’s easy to forget about the little extras that can add up on a Hawaiian vacation. Things like parking fees, resort fees, and higher food prices can blow your budget if you’re not careful.

How to Avoid It:

  • Detailed Budgeting: When planning your trip, add a line item in your budget for miscellaneous expenses. This can include tips, parking, and other unforeseen costs.
  • Educate Yourself on Fees: Many hotels charge resort fees that are not included in the quoted room rates. Check these in advance and factor them into your budget.
  • Eat Like a Local: Save on food by shopping at local markets and eating at places frequented by residents. Not only is it cheaper, but it’s also a great way to experience authentic Hawaiian cuisine. Here are some cheap eats in Waikiki.

Overpacking the Itinerary

The Mistake

There’s so much to see and do in Hawaii that there’s a temptation to cram as much as possible into every day.

This can lead to a hectic schedule, leaving little time to actually relax and soak in the beauty of the islands.

How to Avoid It:

  • Prioritize Activities: Pick a couple of must-do activities and spread them out over your days. Ensure you have downtime planned to just enjoy the beach or resort.
  • Be Realistic: Consider travel time and how activities might tire younger family members. It’s okay to leave some attractions for the next trip! Check out my kid-friendly itineraries for Oahu, Maui, Kauai, and the Big Island.
  • Include Free Time: Some of the best moments can come from unplanned adventures. Leave room in your schedule to explore spontaneously or just unwind.

Biggest Hawaii Planning Mistakes Wrap-up

A trip to Hawaii is a dream vacation for many families, but without proper planning, it can quickly become stressful.

By being aware of common pitfalls and planning accordingly, you can ensure your Hawaiian getaway is as relaxing and enjoyable as it should be.

Remember, the goal is to create lasting memories with your family, not to check off a list of attractions.

So, take it easy, embrace the aloha spirit, and enjoy every moment of your island adventure!

Looking for more Hawaii travel tips? Check out The Hawaii Planning Guide Every Mom Needs: When to Book Everything from Flights to Fun, Beware of Hawaii’s Vacation Rentals: What No One Tells You About Staying with Kids, The Truth About Renting a Car in Hawaii: Mistakes You’re Making Now!, and 10 Insider Tips for Planning an Unforgettable Hawaii Family Adventure!