How to vacation in Maui, Hawaii for under $50!

Aloha! I recently spent 4 nights on the island of Maui, Hawaii and it was a very memorable vacation as my direct flights, four night stay at the Hyatt Regency Maui and 6ltr V8 Camaro SS rental car collectively cost me only $36. It took a bit of planning but definitely worth it.

Booking my flights for $36

The best way to fly direct from Seattle, WA to Maui, HI was Hawaiian Airlines and they happen to be one of the transfer partners with American Express. That gives card holders the opportunity to transfer Membership Rewards points to Hawaiian Airlines 1:1 with a tax offset.

In my case, I was looking to book the first week of November and the total cost for roundtrip tickets was $527 in main cabin. This was initially a buzzkill as these were really expensive flights.

However thankfully, this same leg costed 40,000 Hawaiian Miles + $12 in fees.

All I had to do now, was log into my American Express account, connect my Hawaiian Airline account# and transfer the needed points, which had a $24 excise tax offset fee.

The roundtrip hence set me back 40K points and $36 in fees effectively netting me a 2.45CPP value.

Booking my free stay

I am a Hyatt Globalist and have benefitted greatly by having status with said brand. I wanted a great stay and experience with as many included amenities as possible. The Hyatt Regency Maui Resort & Spa is one of the best hotels on the island of Maui and it also had a Regency Club which meant I could get free breakfast, snacks and dinner on property thanks to Globalist status.

Accordingly, I booked a standard stay for 4 nights for 100,000 World of Hyatt points – some of which I earned from my Chase World of Hyatt Visa Credit Card and rest from my Chase Sapphire Reserve Card.

I was upgraded to an oceanfront room a week prior to check in and the same stay would’ve costed a whopping $4782.

This stay included free breakfast, snacks during lunch, light dinner and dessert plus valet parking which was $40/night ($200 total value) that effectively net me 5CPP value on this booking.

Booking my rental car

Earlier in the year I had gotten the Capital One Venture X card which gave me direct President’s Circle status with Hertz and I used that to book my car rental. I was able to book a mid size car which would then receive a class upgrade and to my surprise, they had a 2020 Camaro SS waiting for me. While it was awkward to get in and out of, it was one beast of a car with a V8 engine that made way more horses than my Lexus GS did back home. Needless to say I was spoilt. I was still charged the base discounted rate (that I received with my Venture X) which came out to $200 for 4 days.

The Venture X gives cardholders a $200 travel credit that is triggered when booking travel (in this case rental car) from their site. Hence, the rental actually cost me nothing as it was fully covered.

Final Thoughts

Now that the most expensive parts of my trip were covered, I was able to really enjoy my vacations and I had more money leftover in my budget towards experiencing a Luau, snorkeling, and amazing restaurants around the island of Maui. All added up (incl fuel), I spent less than $500 on this vacation and that’s probably a win for me in the books.

So, when are you planning your trip to Maui, Hawaii?