This post may contain affiliate links; please read our advertiser disclosure for more information.Hyatt Regency MauiI don’t think my wife would like me talking about how old she is, but let’s just say it is a bigger birthday. You could say she is celebrating turning 30…for a second time, ha! We have been going back and forth on destinations too. Originally the plan was to go to Europe for the Christmas Markets since her birthday is in December. With the current covid rules in place, and me getting it for a second time last month, potentially both being stuck overseas didn’t seem prudent. Especially with it likely rolling into the holidays if it should happen. Our back up plan was Maui. Easy, right? Not so much! I’ll share with you how I ended up travel hacking Maui and turned an $9000 trip into a few hundred dollars out of pocket.Award Flights To MauiNon Stop From Detroit To HonoluluChecking Flights to Maui InsteadSearching High An Low For A Flight OutCircling Back To American Airlines As A Stop GapTravel Hacking Maui: Booking A HotelWaldorf Astoria Grand WaileaAndaz MauiHyatt Regency MauiTo Road To Hana Or To Not Road To Hana?Car RentalLocking In Now But Room For AdjustmentsTravel Hacking Maui – Final ThoughtsLearn more about this card and its features!Award Flights To MauiThe goal was to book lie flat, if possible, for at least some of our flights. It takes us longer to get to Hawaii than it does to get to Europe after all.  We have a pretty great guide on the site showing which routes have lie flat seats.Non Stop From Detroit To HonoluluOne such route is starting up service again in November, Detroit to Honolulu. That was where I started my search. The plan was to spend a few days in Waikiki and then jump a short flight to Maui after.  There was space but it was costly.  Delta wanted 130,000 Skymiles per person one way, ouch! They earned the skypesos moniker right there. I searched partners Virgin and Flying Blue but nothing showed there either.  That seemed like a tough pill to swallow and would require me transferring most of the miles in from Amex Membership Rewards, not something I wanted to do.Checking Flights to Maui InsteadI have been sitting on a stash of American Airlines miles for several years now and had used them to book our 15 year anniversary trip to Maui. We ended up having to cancel that booking because of covid but I figured that was a good place to check. I was even able to get lie flat through Dallas (DFW) back in 2020 for 67,000 miles (I think) a person one way.  Could lightning strike twice? Nope!I did find some decent award pricing coming back from Maui. We would connect through Phoenix and it was 50K a person one way plus the $5.60 in taxes and fees. That seemed like a deal these days, especially with domestic travel, so I booked it. We weren’t getting our desired lie flat seats, but the times of the flights were good, and regular first class is good enough for us.Hyatt Regency MauiSearching High An Low For A Flight OutI really wanted to get her in a bed for her birthday, if I could, so I searched high and low for the flights out. I started searching all of the west coast gateway cities for decent award space. Seattle, San Francisco, Los Angeles were all on the docket. I would then try to tack on a positioning flight if possible or book it separately.The plan was to focus on miles I already had in my accounts versus needing to transfer. That included searching British Airways Avios for American flights, Lifemiles for United Flights and more Virgin Atlantic for any Delta options from the West Coast. Nothing was coming up in any partner searches.I then tried United miles, which we had a nice stash of from the United Quest card. The best thing I could find was 60K a piece from San Francisco and in the dreaded 2-4-2 business class cabin. At that price, for those seats, no thanks.I did find a decent price out of Seattle on Delta. It was 43,000 Skymiles per person in domestic first class, but was a 8AM flight, which meant flying in the night before. That wouldn’t work unless it had to.American didn’t have any great options to Maui or Honolulu from the west coast either.  I even tried Alaska Airlines but they want 60K-80K per person one way for first class.  The one spot I didn’t try was Hawaiian Airlines since I didn’t have any of their miles and nothing was coming up on Virgin.Circling Back To American Airlines As A Stop GapThat left me slinking back to American Airlines. Luckily enough, I was able to find a flight out to Maui through Phoenix for 50K per person. With the ability to cancel award flights without having to pay a fee I decided to lock it up. This gives me the best deal now and then I can continue to check for something that may work better up until we leave in December.Airfare Cost: 200,000 American Airlines Miles & $22.40Cash Price: $4,704Travel Hacking Maui: Booking A HotelAfter my marathon flight search session I figured Hotels would be a bit easier.  Well they were and they weren’t.  There wasn’t a lot of options available, which made the decision easier to make I guess.Waldorf Astoria Grand WaileaI first pulled up Hilton to see if I could burn any free night certificates at the Waldorf Astoria Grand Wailea. On our previous booking I was able to snag a couple of standard award nights here. This time around the lowest priced room was over 500K a night. It looked like a standard room they were playing games with. I searched their award chart for the rest of the year and saw probably less than 10 nights where a standard 110,000 point room was available. I’ll keep checking from time to time up until we go and see if I can snag a few nights.Andaz MauiThe Andaz Maui was another bust. They didn’t have any award rooms available the entire time we were there in December. Not surprising since this hotel is notorious for playing games with award space. Plus, with it being a 35K a night property now I wasn’t overly sad about it. The cash rates were like $1,200+ a night, pass!Hyatt Regency MauiI was starting to sweat a bit at this point. Did I just waste all that time finding flights only to strike out with hotels? That is when the Hyatt Regency Maui came to the rescue! I was able to find award space here and the really nice thing was it was pricing out as off peak. So I only paid 21,000 Hyatt points a night for this category 6 Hyatt. Score! The cash prices were $500-$600 a night.To Road To Hana Or To Not Road To Hana?After reading Jim’s amazing guide on the Road to Hana I was thinking about throwing this into the mix. There is a Hyatt in Hana that had award space. It was also pricing out as off peak. Zack at TPG did a good review on the hotel too.  The place looks like an amazing spot to unplug and get away from a night or two. I mean it doesn’t even have TVs or air conditioning. The problem was with us going in December it would get dark so early, what the heck would we do at night? That plus this being a shorter trip, only 5 nights, we decided this just wasn’t a great fit for us this time. If you are planning on doing the Road to Hana this would be a cool way to break it up. The resort also looks like such a pretty and secluded place to spend a night or two as well.Hotel Cost: 105,000 World of Hyatt PointsHotel Cash Price: $3568.52Car RentalCarmaggedon here we come! This is a cost I was fearing since prices in Hawaii have been sky high since the pandemic.  National was pricing out at $800 for the 5 day rental which was more than I wanted to spend. Luckily, we some free days to use and got the price down to under $300.Car Rental Cost: $279.95Car Rental Original Cost: $800Locking In Now But Room For AdjustmentsOne of the main things I wanted to do while travel hacking Maui, besides save money, was have flexibility. Everything we booked can be canceled without penalty, and that is important. Plans change, now more than ever, so we need to be able to be fluid without having money tied up in vouchers etc. This also allows us to pivot to Christmas Markets (my wife’s first choice) should rules change by December. But, it also allows me to continue to search for other hotels and flights so I can switch it up if we want. These days standard operating procedure should be to book what is the best option NOW since you can always improve on it later. Assuming you book flexible options of course. That is what makes award booking so valuable to me.Travel Hacking Maui – Final ThoughtsThere you have it, that is how we turned a $9000+ trip into $300 out of pocket. I know it isn’t sexy, because it is a domestic trip, but the prices in Hawaii right now are probably as high as pretty much anywhere in the world. It is just nuts out there right now. That is where miles and points can make a huge difference.I am pretty happy with our flight bookings. Spending 200,000 miles isn’t as good of a deal as I may have been able to get 3-4 years ago, but it is better than most of the options out there right now. The big 3 just aren’t releasing space to partner airlines like they used to. Thanks dynamic pricing (sarcasm font)!I was very happy to see a hotel in Hawaii pricing out as off peak. I will take that 20,000 World of Hyatt points savings every day and twice on Sunday. That wouldn’t have been the case a few years ago. So, I guess peak and non peak worked in my favor this time around. The non peak pricing is a savings of around $300 in points for me alone.The hardest thing to hack is car rentals for sure. Booking through a bank travel portal and wiping off the charge with points is probably the best option for most. That or use a travel credit on your credit card on it like you have with the Capital One Venture X or the Chase Sapphire Reserve.Has anyone else booked a trip to Hawaii recently? How did you end up faring?Disclosure: Miles to Memories has partnered with CardRatings for our coverage of credit card products. Miles to Memories and CardRatings may receive a commission from card issuers. Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities.Featured: Chase Sapphire Preferred – Increased 80K Welcome Offer! Chase Sapphire Preferred has an increased offer right now. This is one of the most popular travel cards available. For a limited time you can earn 80,000 Ultimate Rewards points after $4K spend in the first 3 months of having the card while enjoying bonus categories like travel & dining. Points are worth $1K when use towards travel or transfer to partners like Hyatt, United or Southwest! $95 annual fee is not waived.