I don't think my wife would like me talking about how old she is, but it is a bigger birthday. She is celebrating her 30th birthday for the second time. We've been going back and forth on destinations. The plan was to go to Europe for the Christmas Markets 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. If it should happen, it will likely roll into the holidays. Maui was our back up plan. It's easy, right? Not much! I will share with you how I ended up hacking Maui and taking a few hundred dollars out of my pocket.
If possible, the goal was to book lie flat. It takes us longer to get to Hawaii than it does to get to Europe.
Detroit to Honolulu is going to start up again in November. I started my search there. The plan was to spend a few days in Waikiki and then jump a short flight to Maui. Right there, they earned the title of skypesos. I searched for partners Virgin and Flying Blue but nothing came up, so I decided to transfer most of the miles in from Amex Membership rewards.
I have been sitting on a bunch of American Airlines miles for a long time and used them to book our 15 year anniversary trip to Maui. We had to cancel that booking because of covid, but I thought that was a good place to check. I was able to lie flat through Dallas in 2020 for 67,000 miles, and I think I could do it again. Nope!
I found some decent award pricing from Maui. We would connect through Phoenix and it would cost 50K a person, plus $5.60 in taxes and fees. I booked it because it seemed like a deal these days. 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.
I wanted to get her a lie flat bed for her birthday, so I searched high and low for flights out. I started looking for decent award space in all of the west coast gateway cities. Seattle, San Francisco, Los Angeles were all on the docket. If possible, I would try to book it separately.
I wanted to focus on the miles I already had in my accounts. British Airways, Lifemiles, and Virgin Atlantic were searched for Delta flights from the West Coast. Nothing came up in partner searches.
We had a nice amount of United miles from the United Quest card. 60K a piece from San Francisco was the best thing I could find. No thanks at that price for those seats.
I found a good price out of Seattle on Delta. It was 43,000 Skymiles per person in domestic first class, which meant flying in the night before. Unless it had to, that wouldn't work.
I tried Alaska Airlines, but they only want 60K-80K per person for first class.
I went back to American Airlines. I was able to find a flight out to Maui for 50K per person. I locked it up because of the ability to cancel award flights without paying a fee. This gives me the best deal right now and I can continue to check for better deals until we leave in December.
I thought hotels would be easier after my flight search, but they weren't.
I pulled up to the hotel to see if I could get a free night certificate. I was able to get a few award nights here on our previous booking. The lowest priced room was over 500K a night. They were playing games in a standard room. I looked at their award chart for the rest of the year and found a standard 110,000 point room available for less than 10 nights. I will keep checking until we go and see if I can get a few nights.
Another bust was the Andaz Maui. They didn't have any award rooms for the entire time we were there. The hotel is known for playing games with award space. I wasn't sad about it because it was a 35K a night property. The rates for cash were over $1,200 a night.
At this point, I was starting to sweat. I wonder if I just wasted time finding flights and ended up in hotels. The Hyatt Regency Maui came to the rescue. I was able to find award space here and it was pricing out as off peak. I paid 21,000 Hyatt points a night for this category. Score! The prices were in the hundreds of dollars a night.
I was thinking about putting this in the mix after reading Jim's guide. The Hyatt in Hana has award space. It was also pricing out during peak times. The hotel looks like a great place to get away from it all for a while. It doesn't have air conditioning or TVs. We were going in December and it would get dark so early, what would we do at night? We decided this was not a good fit for us because it was only 5 nights and it was a shorter trip. This would be a great way to break it up if you are going to do the Road to Hana. The resort looks like a pretty place to stay for a night or two.
Carmaggedon here we come! I was worried about the cost since prices in Hawaii have been so high since the Pandemic. We got some free days to use and the price was under $300.
Flexibility was one of the main things I wanted to do while travel hacking Maui. We can cancel everything we booked without penalty. We need to be able to change plans without having to use vouchers, and we should be able to do that by December. I can switch it up if we want, because it allows me to continue to search for other hotels and flights. Since you can always improve on it later, it's a good idea to book what's the best option now. You should book flexible options. That's what makes award booking so valuable to me.
We turned a $9000+ trip into $300 out of pocket. I know it isn't sexy, but the prices in Hawaii are pretty much the same as anywhere in the world right now. It is crazy right now. That is where points and miles can make a difference.
I'm pretty happy with our flights. 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 are not releasing space to partner airlines like they used to. Thanks to dynamic pricing!
I was happy to see that the hotel in Hawaii was pricing out at off peak. I will take 20,000 World of Hyatt points every day and twice on Sunday. It wouldn't have been the case a few years ago. I think peak and non peak worked in my favor this time. The non peak pricing saves me around $300 in points.
Car rentals are the hardest thing to hack. Booking through a bank travel portal and wiping off the charge with points is the best option for most. You can use a travel credit on your credit card like you do with the Capital One Venture X.
Has anyone else booked a trip to Hawaii recently? How did you end up faring?
We have a partnership with Card Ratings for our coverage of credit card products. Card issuers may give a commission to Miles to Memories and Card Ratings. The author's opinions, reviews, analyses, and recommendations have not been reviewed, endorsed or approved by any of these entities.
Chase Sapphire Preferred - Increased 80K Welcome Offer!
There is an increase in the offer of Chase Sapphire Preferred. One of the most popular travel cards is this one. For a limited time, you can earn 80,000 Ultimate Rewards points after spending $4000 in the first 3 months of having the card. Points are worth $1K when used towards travel or transfer to partners like Hyatt, United or Southwest.
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