An Anniversary Trip to Kauai and Maui — Reader Success Story

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Today I want to share a story from TPG reader Rance, who used points to cover flights and hotels for a two-week vacation in Hawaii. Here's what he had to say:

My wife and I wanted to take a special trip for our (belated) 10-year anniversary. I had over 100,000 United miles from my own travel and the sign-up bonus on the United MileagePlus Explorer Card (offer no longer available), and we had never been to Hawaii, so the search was on. I found great saver award availability in April 2018, and was able to book our flights from Cleveland to Kauai, Kauai to Maui, and home from Maui to Cleveland for 104,000 miles, with a redemption rate of approximately 2.4 cents per mile. We upgraded to Economy Plus for a couple of the longer legs (and I used my Chase Sapphire Reserve card to make sure we earned 3 points per dollar on travel).

For hotels, I redeemed 198,000 Ultimate Rewards points (earned from sign-up bonuses and maximizing bonus spending over several years) for six nights in a club room at the Grand Hyatt Kauai, which worked out to about 3.1 cents per point. We wanted to stay at two places in Maui: first, we used 60,000 Starpoints (earned from the sign-up bonus and spending on the Starwood Preferred Guest® Credit Card) for three nights at the Westin Ka'anapali Ocean Villas, with a redemption value of 2.6 cents per point. We then booked four nights in an Ocean View Suite at the Andaz Maui. Because we couldn't find award space, we redeemed approximately 236,000 points through the Ultimate Rewards Travel Portal at 1.5 cents per point.

We also took advantage of some other Sapphire Reserve benefits during our trip. We used Priority Pass for a fantastic breakfast at Bar Symon in Cleveland, and I used the Troon golf program for a $99 round at the King Kamehameha Golf Club on Maui (which is normally a private club). We had an amazing two-week vacation, and since the hotels and flights were covered with points, we were able to do more tours, such as a private helicopter ride on Kauai! Paying for the flights and hotels out of pocket would've cost us over $14,000! We've taken trips using points before, but this was definitely our best.

Rance's flights provide an interesting case study of how to decide which points or miles you should use for a given award. He paid 45,000 MileagePlus miles per person for United flights to and from Hawaii. Alternately, he could have transferred from Ultimate Rewards to Singapore Airlines to book the exact same flights for 40,000 points per person. In either case he gets a good redemption value, but while saving 10,000 miles total might seem like a no-brainer, the comparison isn't as straightforward as it seems.

Transferable points generally have much greater potential than miles in an individual airline program, which is why I value them so highly. Given the choice between redeeming 80,000 Ultimate Rewards points and 90,000 MileagePlus miles, I'd rather pay a modest nominal premium (12.5% in this case) to use the less valuable United miles first. In Rance's case, the decision is a bit murkier when you consider other redemption options like booking Delta flights through Korean Air (for 25,000 miles round-trip in economy). Those itineraries would likely have involved more stops, so he'd have to weigh any points saved against the time lost in transit.

This kind of comparison is one reason why I publish valuations of major loyalty currencies: When all else is equal, you should choose the least "expensive" award based on what you think is a reasonable expected redemption value, even though it might not be the cheapest award in terms of the total points needed.

I love this story and I want to hear more like it! To thank Rance for sharing his experience (and for allowing me to post it online), I’m sending him a $200 airline gift card to enjoy on future travels, and I’d like to do the same for you. Please email your own award travel success stories to info@thepointsguy.com; be sure to include details about how you earned and redeemed your rewards, and put “Reader Success Story” in the subject line. Feel free to also submit your most woeful travel mistakes. If your story is published in either case, I’ll send you a gift to jump-start your next adventure.

Safe and happy travels to all, and I look forward to hearing from you!

Feature photo by Matt Anderson Photography / Getty Images.