We are heading back to Hawaii. I’m pretty excited about it and decided to write an article while I’m paying for stuff rather than after the trip. The plan is to go to Kauai first and then to the Big Island. We really liked Kauai last time, but only had 4 nights there. This time we are spending 2 weeks. The last week we will stay in Kona.
Flights
We live in Austin and so you can get a roundtrip for around $500. A couple years ago Hawaiian Airlines introduced a direct flight from Austin and we managed to get first class seats for 40K each way which was a great deal as it is around $1500 for the seat. Currently I have a companion pass, so it was tough to justify buying two tickets when I could buy one. So one way we are flying Southwest and the other Hawaiian first class.
Southwest: $300
Hawaiian: $240 + 25K points to upgrade
Flight between islands: $60
Per person this comes out to $600 + 25K points for an upgrade.
Housing
Hawaii is expensive. Last time we rented an Airbnb for a month and that cost $5,000. This time I used a TON of Wyndham points to stay. I got the credit card and purchased the maximum number of points and my wife did the same. You can use Wyndham points on Vacasa if the price isn’t too high (around $300 or less). Normally it is 15K points per bedroom per night, but you get 10% off if you are a cardholder. So 21 nights cost 283,500 points. That’s equal to 2 60K signup bonuses plus purchasing 163,500 points. I purchased that amount of points for around $1600. Altogether that comes out to around $77 a night which is amazing. The actual rates of the stay would be around $8000 since there are a lot of fees like cleaning, booking, and taxes which you avoid with points.
Transportation
We are going to rent cars in both places. That is $1200 plus gas. I don’t buy the insurance because my credit card covers it. In fact, in Maui the roads were so narrow that my rental got a tiny scratch and we were charged $150 for it. But my Chase card reimbursed me. Meanwhile, in Costa Rica we were forced to pay $40 a day for insurance because they said that is the country law. That was more than the cost of the rental!
Food and Activities
Currently unknown, but I wrote about them last year here if you want to check it out.
Conclusion
Before even setting foot on a plane, we have spent $4600, 75K airline points, and 120K hotel points. Going on a trip to Hawaii isn’t a cheap proposition, but I’m doing my best to mitigate the costs. There are people paying $5000 for a week at a resort, so I feel pretty good about this cost given what we are getting in return.