I've visited Hawaii more than 40 times and I know ALL the tips and tricks for planning the ultimate Hawaii family vacation! I offer free Hawaii planning email courses. I also send weekly emails on Fridays where I share my top things to do in Hawaii with kids, the best family resorts in Hawaii, and my ultimate packing lists! Mahalo!
The Hawaii Planning Mistake 90% of Families Make
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Aloha Reader! I need to tell you about something that's been breaking my heart lately. Last week, I got an email from Sarah, a mom of three who'd been planning their dream Hawaii trip for over a year. They saved up, booked their flights, found the perfect condo rental... and then discovered they couldn't do ANY of the activities her kids had been most excited about. No Diamond Head sunrise hike. No Haleakala crater viewing. No snorkeling at that special spot she'd been promising them. All booked up. Sometimes months in advance. Sarah's story isn't unique. I'm hearing it over and over again, and it's absolutely preventable. Here's the thing: Hawaii trip planning has completely changed in 2025. The old advice of "just book flights and hotels, then figure out activities when you get there"? That'll leave your family staring at "SOLD OUT" signs everywhere. My friend learned this the hard way on her most recent trip when she tried to grab last-minute tickets to the USS Arizona Memorial. The woman at the desk just laughed (kindly, but still) and said, "Honey, we're booked solid for the next two months." The #1 mistake families are making? Not booking activities and attractions when they book their flights. I'm talking about reservations for:
But here's what makes me really sad – it's not just about missing out on activities. When families can't do what they planned, they end up:
The good news? Once you know the new rules, planning is actually easier than ever. I've completely updated my approach for 2025, and families who follow my new timeline are having BETTER trips than before – less crowded experiences, smoother logistics, and way less stress. Want to know exactly how to avoid the planning pitfalls that are catching so many families off guard? I've written detailed guides that walk you through everything: 🌺 What I Wish I Knew Before Going to Hawaii with Kids – This covers all the insider tips I've learned from 40+ trips, including what to book first 🏝️ Best Things to Do on Oahu with Kids – 101 activities with specific booking requirements and timelines Plus, if you're planning fall travel (which is looking AMAZING this year), check out my September guides:
My new 2025 planning timeline (bookmark this!): 6 months before: Book flights, accommodations, and car rentals Trust me, following this timeline will save you from so much heartache. And honestly? Your trip will be better because you'll have access to experiences that spontaneous planners simply can't get. Don't let poor planning turn your dream Hawaii vacation into a series of "sorry, we're booked" conversations. Your family deserves better than that. Got questions about what to book first for your specific trip? Just hit reply – I'm always here to help! Aloha, Marcie P.S. – Already feeling overwhelmed by all the new planning requirements? That's exactly why I created my detailed planning guides. They do the research FOR you so you can focus on getting excited about your trip instead of stressed about logistics. |
Aloha! I'm Marcie with Hawaii Travel with Kids
I've visited Hawaii more than 40 times and I know ALL the tips and tricks for planning the ultimate Hawaii family vacation! I offer free Hawaii planning email courses. I also send weekly emails on Fridays where I share my top things to do in Hawaii with kids, the best family resorts in Hawaii, and my ultimate packing lists! Mahalo!
Aloha Reader! I'm just going to be upfront with you: Hawaii is not cheap, and the numbers have gone up. If you've been Googling "how much does a Hawaii trip cost" and getting estimates that feel surprisingly low, it's probably because those articles are using old data. Here's what the realistic picture looks like for a family of four in summer 2026. Flights This is where a lot of families get sticker shock. The old benchmark of $450 to $900 per person roundtrip that you'll still see in a lot...
Aloha Reader! I got a version of this question a lot in February: "We have 10 days in Hawaii. Should we do one island or two?" Sometimes it's "should we do Maui or Oahu for our first trip." Sometimes it's "we really want to see both but we're not sure we have enough time." The wording changes but the underlying question is the same. How do we make sure we're making the right call on something this big? Here's the honest answer: it depends, and the things it depends on are really specific to...
Aloha Reader! Here's something I wish more families knew before they started planning: the activities are not something you figure out once you get there. The good ones sell out. Sometimes months out. And finding out your must-do luau has no availability for your dates is a really deflating moment when you're excited about a trip. So let's talk about what to book, when to book it, and a couple of things to watch out for. Before anything else, check the fine print. If anyone in your family...