I’ve been very fortunate to stay at some pretty nice hotels.
A few years ago, I stayed at the Grand Wailea on Maui for a night. I was (as far as I could tell), the only traveler staying there who was either solo or not on a honeymoon. The Grand Wailea is a Hilton property, so I was able to use points for the transaction, so it cost me nothing. Had I paid in cash, it would have been upwards of $500.
A year or two later, I stayed at Koloa Landing on Kauai. At the time, the property was under the Wyndham organization (yes, the same organization as Days Inn and Ramada) and I was able to secure three free nights there on points, again saving $500 a night or so.
These were amazing experiences.
In the travel trade, these types of hotels are known as “aspirational“. They are the hotels of the type that people stay at for once-in-a-lifetime experiences. They often include water as part of the appeal, either ocean-side or over-the-ocean (such as the various over-water bungalow hotels).
While I’m grateful for the ability to have had these experiences, and wouldn’t trade them for anything, I want to explore the flip side. Because depending on how you look at it, these hotels might not be the best use of your hotel points or the best focus of your earning strategy.
(They certainly aren’t the best use of your money, but we’re assuming that no one here would ever pay cash for one of these hotels, at least until you’re wealthy enough that it doesn’t matter.)
In fact, I will argue that there is a case for foregoing any but the most basic hotels using points.
Am I suggesting that we aspire to Candlewood Suites instead of over-water bungalows?
Maybe. Hear me out.