Aloha Reader!

I need to tell you about an email I got last week that made my heart absolutely sink.

A mom named Jen wrote to me about her family's "dream" Hawaii trip that turned into a complete disaster. They'd saved for over a year, planned everything perfectly (or so they thought), and ended up with disappointed kids, blown budgets, and memories they'd rather forget.

The worst part? Every single thing that went wrong was 100% preventable.

I've been to Hawaii 40+ times, and I can tell you that travel fails happen to EVERYONE. But after hearing story after story like Jen's, I realized we need to talk about this stuff openly so other families don't make the same mistakes.

So I'm going to share some real stories from real families (with permission) – not to embarrass anyone, but because learning from other people's mistakes is so much less painful than learning from your own!

The "We Didn't Check Our Flight Times" Disaster

One family found "amazing deals" on flights to Maui and booked immediately without looking at the fine print. The reality hit when they got their boarding passes: 6am departure (meaning 2:30am wake-up for the kids), layover in Phoenix, and arrival in Maui at 11pm local time.

They were so exhausted they basically lost their entire first day sleeping until noon instead of hitting the beach. Saving $600 per person cost them a full day of their expensive Hawaii vacation.

The "Haleakala Sunrise Reservation" Heartbreak

A dad planned his entire Maui trip around watching sunrise from Haleakala crater. Woke the family up at 3:30am, drove an hour and a half in the dark, only to find the park entrance gate closed with a sign about requiring advance reservations.

His kids were devastated. They'd been so excited, and now they were sitting in a cold parking lot watching other families with reservations drive past them into the park.

The "No Rental Car Available" Panic

A family booked flights six months ahead but waited on the rental car "to see if prices would drop." Two weeks before their trip: zero cars available from any company. They spent $1,400 on Uber/Lyft for the week and couldn't access any of the beaches or hikes they'd planned.

Here's what breaks my heart: ALL of these disasters were preventable with better planning and the right information.

The good news? I've learned from these mistakes (and my own!) so you don't have to.

Over my 40+ Hawaii trips, I've figured out exactly what works, what doesn't, and how to avoid the pitfalls that catch most families off guard.

Want to make sure YOUR Hawaii trip doesn't become a cautionary tale? I've put together all my hard-won knowledge in detailed guides:

🌺 Things I Wish I Knew Before Going to Hawaii with Kids – All the insider tips that prevent common disasters

🚗 Hawaii Car Rental Mistakes – Don't get stuck without a car like that family did!

📍 Hawaii Mistakes Every Tourist Has Made – Learn from common fails across all islands

And because specific islands have specific pitfalls:

• ​Oahu Mistakes – Avoid Waikiki tourist traps and timing disasters
• ​Maui Mistakes – Including that Haleakala reservation requirement!
• ​Big Island Mistakes – Volcano viewing and logistics fails

My quick "prevent major fails" checklist:

✅ Book flights AND rental cars at the same time (don't wait!)
✅ Research reservation requirements for popular attractions immediately ✅ Check TOTAL flight times, not just prices
✅ Budget 30% more than you think you'll need
✅ Have indoor backup plans for rainy days

Look, even experienced travelers have things go wrong sometimes. But the difference between a minor hiccup and a vacation disaster usually comes down to preparation and realistic expectations.

Your family deserves an amazing Hawaii experience, not a series of preventable disappointments.

Have you had a Hawaii travel fail that could help other families learn? Hit reply and share it with me – your experience could save someone else's vacation!

And if you're planning a Hawaii trip and want to avoid these common pitfalls, dive into those guides above. They're packed with the real-world, tested-by-experience advice that actually prevents problems.

Sending you aloha (and hoping for fail-free travels!),

Marcie

P.S. – I've created a bunch of Hawaii travel guides that will save you from making mistakes like these!