Hawaii is one of those destinations people assume is only realistic for luxury travelers or once-in-a-lifetime splurges. Between flights, resort hotels, and the reality of booking during school breaks, the price tag adds up fast for families.
We’ve now been to Hawaii multiple times as a family — twice to Maui, plus trips to Kauai and the Big Island, and even a day trip to Oahu to visit Pearl Harbor. Each of these trips would have cost us thousands of dollars out of pocket if we paid in cash.
Instead, we’ve used points and miles to dramatically reduce the biggest costs of our Hawaii trips: flights and hotels. This page is your starting point for everything I’ve shared about traveling to Hawaii with kids on points and miles — real itineraries, hotel stays, snorkeling spots, island hopping tips, and honest cost comparisons.
If Hawaii feels like a “someday” trip for your family, this guide will walk you through what we’ve actually done and where to start.
How We Fly Our Family to Hawaii Using Points and Miles
Flights are usually the most expensive part of a Hawaii trip, especially when you’re booking multiple seats during peak school break travel. Using airline miles and flexible points has allowed us to cover most (and sometimes all) of our airfare, which is what makes Hawaii trips realistic for our family.
We’ve also combined islands on a single trip by booking short inter-island flights, which lets us see more of Hawaii without needing separate round-trip flights back to the mainland each time.
If you’re curious how island hopping works in practice, you can read more about how we plan those routes here: Hawaiian Island Hopping
Our Hawaii Travel Guides (Island by Island)
Below you’ll find our real trip guides for each island we’ve visited so far. Each post includes where we stayed on points, what we did with kids, and how we paced our days.
Maui on Points and Miles (Visited Twice)
Maui is one of the best all-around Hawaii islands for families. We’ve been twice, which means we’ve experienced different styles of trips — snorkeling days, beach time, and mixing in sightseeing without overpacking the schedule.
If snorkeling is on your list, here’s where we took our kids and how we stayed at a resort using points:
Best Maui Snorkel Beaches for Families + How We Stayed at a Hyatt Resort Using Points
If you want a full example of how to structure a Maui trip with kids, this post walks through our exact 5-day itinerary:
How My Family Enjoyed a 5-Day Maui Adventure: The Ultimate Guide to Traveling on Points and Miles
The Big Island on Points and Miles
The Big Island feels completely different from Maui. It’s more spread out, more adventurous, and perfect for families who want a mix of beaches, volcanoes, and outdoor exploring.
This is our complete Big Island planning guide, including where we stayed on points, what we ate, and what we explored:
The Ultimate Big Island Guide: Where to Stay on Points, Eat, and Explore
We also put together a guide to some of the less crowded beaches we loved on the Big Island, many of which are easy to pair with hotels you can book using points:
10 Hidden Beaches on the Big Island You Can Visit with Points and Miles
Kauai on Points and Miles
Kauai is one of the most naturally beautiful islands we’ve visited and is a great option for families who love hiking, scenic drives, and slower travel days mixed with beach time.
Here’s our full Kauai planning guide, including how we structured the trip using points and miles:
Kauai Travel Guide: How We Traveled on Points & Miles
If you’re deciding between Maui and Kauai, this hotel comparison breaks down two popular resort options we’ve stayed at:
Hyatt Regency Maui or Grand Hyatt Kauai on Points
Oahu Day Trip (Pearl Harbor)
On one of our Hawaii trips, we also did a day trip to Oahu specifically to visit Pearl Harbor. This was a meaningful way to incorporate history and learning into our travel experience, especially for our kids.
If you’re planning to island hop, Oahu can be a worthwhile add-on for historical sites and cultural experiences, even if you don’t stay overnight.
What Hawaii Would Have Cost vs. What We Actually Paid
Hawaii is one of those trips where the cash prices can be shocking once you add up flights, resort hotels, and family-sized rooms. This is where points and miles make the biggest difference for us.
I’ve shared more about how expensive family travel can be — and how we try to be strategic about saving on big-ticket trips like Hawaii — in this post:
7 Expensive Family Travel Experiences — and Smarter Ways to Save Big
Seeing the side-by-side numbers is often what helps families realize that trips like Hawaii aren’t just for influencers or luxury travelers — they’re possible with the right strategy.
How to Start Planning a Hawaii Trip on Points (Beginner-Friendly)
If you’re new to points and miles, Hawaii can feel overwhelming. Multiple islands, limited award availability, and expensive resorts can make it feel complicated.
You don’t need to master everything at once.
A simple way to start is by focusing on one part of the trip first:
– covering flights with miles
– or learning how hotel points work
From there, you can layer in more advanced strategies like island hopping or mixing points and cash stays.
If you want to see the exact cards and strategies we use to earn points for trips like Hawaii, you can find them here: [BEST OFFERS HERE]
If you’re unsure what makes sense for your situation, feel free to message me on Instagram @pointsandmilesteachers before applying for anything. I’m always happy to help you think it through.
Where to Start If Hawaii Is on Your Wish List
If Hawaii feels like a lot to plan, start with one island and one goal. Maui and the Big Island are both great first Hawaii trips for families because they’re easy to pace and have a mix of beaches and activities.
This page will continue to grow as we take more Hawaii trips and add new itineraries, hotel reviews, and planning guides. Bookmark it if Hawaii is on your family’s future travel list — I’ll keep updating it as we go.
