To get ourselves to Hawaii, we took a pretty convoluted route. That sometimes has to happen to get a good deal! First we wanted to use our American Express reward points we get through the American Express Platinum card and the Every Day Preferred American Express card.
We were aware that United Airlines flies to Hawaii. United is in the Star Alliance with Singapore Airlines. We also knew that Singapore could have better deals than United. Also, Amex points don’t transfer to United but they do transfer to Singapore. Now when airlines are in an alliance together, you can usually book a flight for the Airline A through the website of Airline B, using the points from Airline B to either get a better deal or catch a flight that Airline B does not offer but Airline A does. So in this instance, we could go to the Singapore Airlines website (since they do not offer a flight to Hawaii, it would show the United flight) which we could then pay for with our Amex points which we transferred into Singapore KrisFlyer points 1:1.
Once we found the flight from Atlanta to Honolulu that we wanted, we called Singapore Airlines to have them book the flight for us using our KrisFlyer points. In this situation it’s just better to call. I think it’s easier when booking with points and it also makes sure of everything. Phantom availability does exist. That’s where the flight shows there to be seats, but then there really isn’t. The Singapore employee on the phone may also be able to hold the flight for you while you wait for your points to transfer over if they haven’t already. In this situation, we spent about 30k Amex points (and $11.20 for taxes and fees), per person to fly round trip to Hawaii. It would have cost 45-90k United Airlines miles if we had just booked through United using our Chase points. Delta would have cost about 63-80k Skymiles round trip.
Of course our flights were not direct. Going out, we went through Denver. Coming back, we went through San Francisco and Denver to get back to Atlanta.
I know this might have gotten pretty confusing. In this situation, if you had Chase points to use, you can also transfer your points to Singapore and do the same thing. With Amex points, we could have also booked through Delta. We found Singapore to be a lot cheaper. Also take note that points transferred into Singapore KrisFlyer points take usually around 24 hours. Unlike other point transfers, it isn't instant.
So that's enough about flights. Now to where to stay!
When we were in Hawaii, we stayed in O’ahu for a few days and then went to Maui. We took a Hawaiian Airlines flight to hop over to Maui. Just like the whole ordeal above, we didn’t just buy our flight through Hawaiian. First we transferred our Amex points to Delta Skymiles 1:1. Delta is in an alliance with Hawaiian Airlines. We went on the Delta website and searched for the Honolulu to Maui flight we wanted and simply booked it with our Delta Skymiles.
In O’ahu and Maui we found that Airbnbs were the most convenient and inexpensive for what you get. In O’ahu we wanted to be close to Waikiki, but be farther enough away that the price dropped. Right out from the city, about a five minute walk was a studio for $75/night. One bed, one bath, a kitchenette, and a legit hair blow dryer! I got me one of the same type when I got home. It had a view of Diamond Head and was a quick walk to the strip of restaurants and hotels. That was great for us because we ended up picking up buses in town almost every morning for our activities around the island. Across the street from our place was an affordable and yummy sushi place and a health café with cool smoothies and sandwiches.
Our second Airbnb in Maui was a bit of a risk for us, because this was our first time staying in a place with a host. But Priscilla was awesome!! It was $98/night because everything is more expensive in Maui. So the set up was perfect: there was a front door that led into the hall with the front bedroom and bathroom attached to the hall. Then there was another door that closed off the rest of her house. That way she had privacy and so did we! We did share the bathroom with her but honestly, we hardly noticed her ever in there. She left us breakfast every morning and our room came with a massive good basket of drinks and chocolate. The condo complex has a pool directly by the sea. We could drive to downtown Lahaina or up the bays to snorkel really easily. We really enjoyed this place!
When we were in Maui, we also needed a rental car. I don't think one is necessary in O'ahu. You can get a bus, an Uber, or just walk. Maui is a lot more spread out and will require a car. Plus don't you want to do the road to Hana? That being said, we rented from Hertz and got a Nissan Rogue.