If you’ve ever thought a trip to Hawaii felt out of reach, I get it! We used to think the same thing. But this trip is the perfect example of how points, miles, and built in credit card perks can turn a “once in a lifetime” vacation into something that actually feels not only doable, but repeatable! We actually booked a return trip for next year while sitting by the pool during this trip!
If you want a visual breakdown, make sure to check out our “Maui” highlight on Instagram but here’s the full story of how we made our 6 night trip to Maui for a family of four happen.
GETTING TO MAUI:
Instead of flying directly from our current home airport to Maui, we repositioned to the west coast where award flights are not only a better value but more widely available. This does require a bit more flexibility as we always reposition a day before to leave time for any travel related delays but when the redemption is too good to pass (like what we booked) it’s worth it!
MCI to SFO using United miles (only 13.5k points per person) for 3 of us plus $16.80 total in taxes/fees.
We used United Travel credits for the 4th ticket that was priced at $250. We fund our Travel Bank utilizing our American Express Aspire airline credit ($50 per quarter). We have 3 of these cards so that’s $150 per quarter. We also utilized our American Express Platinum airline incidental fee with an additional $400 per year (we have 2 Platinums) Unfortunately, this loophole is no longer an option but it’s still available with the Hilton Aspire!
We then had to get to Oakland where we found a flight on Hawaiian for 17.5 points per person! We transferred 17.5 American Express Membership Rewards to Hawaiian Airlines when the transfer partnership was still open last year to book these flights.
We used our Uber credits from 2 American Express Platinums and 1 American Express Gold to cover our Uber from SFO to a nearby hotel at OAK.
We booked our hotel using our $150 Delta Stay credit from my American Express Delta Platinum card.
The next morning, we woke up bright and early to catch our 7:00am flight from OAK to OGG.
By utilizing points and card benefits/credits, we drastically reduced what would normally be one of the most expensive parts of the trip.
WHERE WE STAYED
We booked 5 night at the Wailea Beach Resort – Marriott. Marriott allows you to book 4 nights with points and get the 5th night free! We used a total of 403K Marriott Bonvoy points for this stay. We earned these points through SUBS on both the American Express Marriott Bonvoy Brilliant AND the Chase Marriott Bonvoy Boundless cards. My husband and I both got these cards during our last PCS when they had elevated offers. Our PCS expenses helped us hit not only these bonuses but 2 addtional cards as well! PCS time is such a great opportunity to really rack up points! We also earned additonal points with our regular spend, referrals and my daugther won an insane amount of points (almost 80K) when she spun the wheel at the check-in counter the night we moved out of our house to hit the road for Kansas!
The American Express Marriott Bonvoy Brilliant comes with automatic platinum status which (at this property) gives us breakfast coupons for 2. Due to a slightly hectic check-in, they actually ended up giving us enough coupons for all 4 of us. So that meant we had breakfast covered for our entire stay!
The biggest con (in my opinion) with Marriott is that reward stays do NOT get resort fees waived. While not the end of the world, it’s eye roll worthy when you know Hilton and Hyatt do this. So, we did end up paying $59/night for the resort fee but I can’t complain since we paid $0 to actually stay there! They aslo do have an incredible resort with amazing amenities. Great options for family friendly and adult only pools, Ukulele lessons, Lei making classes, Hula lessons and much more!
For our last night, we moved a whole 5 minutes down the road to The Grand Wailea, A Waldorf Astoria Resort. We utilized one of our free night certificates that we earn yearly from on of our American Express Aspire cards. My husband had one that was going to expire at the end of the month so it was perfect timing. This $1200/night room cost us $0 and 0 points. We also received a $50 food and beverage credit as diamond members and did not pay the resort fee as this was an award booking. We also had resort credit from our Aspire cards but I’ll go into detail more on that below. This resort was great! I have heard mixed reviews but we had a good time. The pools are unmatched, the rooms were spacious and the and the grounds were stunning.
HOW WE SAVED:
This is where having the right cards in both of our names really made a HUGE difference and why you will always hear us say to have one of each card for the service member AND spouse. It’s literally free money….because for the majority of cards, we aren’t paying the annual fee =0
Here are all the credits we were able to utilize on this trip:
- $600 in resort credit at the Grand Wailea (American Express Aspire x 3)
- Think pool side lunch and drinks, pre dinner drinks, fancy dinner at Humuhumunukunukuāpuaʻa, valet parking…etc.
- When we checked out, we just had them put $200 on each of our cards
- $900 in travel credit (Chase Saphhire Reserve x3)
- 1 per person and my husband upgraded his Freedom Unlimited to a second reserve
- Whale tour (x2 because it was just that good!), a rental car…anything that codes as travel on your statement will receive a credit up to $300 per anniversary year
- $450 dining credit (Chase Sapphire Reserve x3)
- Each card offers $150 bi-annually dining credit at restaurants booked via the Chase Sapphire Reserve Exclusive Tables program on Open table (enrollment required)
- We used a portion of this to cover dinner one night at Lineage located right across the street from our first hotel (Wailea Beach Resort)
- $250 Resy credit (American Express Platinum x2 + 1 Gold )
- Amex platinum offers $100 per quarter and the Gold card offers $50 semi annually
- We used a portion of this to cover dinner one evening at Sale Pepe
All of this left so much more wiggle room in the budget for other amazing dinners, souvenirs and overall just a general sense of peace and relaxation NOT being stressed financially.
Unfortunately, this trip did have to come to an end.
HOW WE GOT HOME:
We flew OGG to MCI via LAS on Southwest. My husand and I BOTH have the Southwest compannion pass so we only had to purchase our flights for 33k points each and then each of our girls flew for only the price of taxes and fees ($5.60). So all in, 66k points + $22.40 got us back home.
Side note: If you’re ever in the Las Vegas airport- don’t skip the Chase Sapphire Lounge by The Club. It was GREAT! Giving many Centurion Lounges a run for their money.
You can access this lounge (and have up to 2 free guests) with a Chase Sapphire Reserve, J.P. Morgan Reserve or The Ritz-Carlton card (unlimited guests with this one). If you don’t have one of those but do have a card that comes with a Priority Pass Select membership (American Express Platinum, Marriott Bonvoy Brilliant…etc) you get ONE complimentary pass per year.
THE BEST PART
This trip didn’t feel like a “once in a lifetime” splurge. I actually booked another 5 night stay at the Hyatt Regency for next year while sitting by the pool on THIS trip!
Because we used points and credits strategically, it felt repeatable.
And that’s really the goal. Using travel rewards not just to take one amazing trip, but to make travel something you can realistically do again and again.
If you’re just getting started, don’t feel like you need every card I mentioned . Start with one, learn how to maximize it, and build from there.
Hawaii is expensive. There’s no way around that. But with the right plan, you can dramatically reduce your out-of-pocket cost while still having an incredible experience.
-Amy
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