A Vacation Regret

The Royal Hawaiian Entry

Many people, including me, spend lots of time saving up for a dream vacation.  Some people save up points/miles and some save cash.  No matter what your currency, the idea is that you’re planning a dream vacation and want to enjoy every aspect of it.  Some people save for a lifetime and only get to go on one vacation while many people who maximize their points/miles earnings can go on many vacations in their lifetime.  No matter how many vacations you go on, no one wants to have vacation regret.

This past year I saved for a three-week trip to Hawaii. I saved up 165,000 Starwood Starpoints for 18 nights in Hawaii, 50,000 US Airways miles for airfare, 150,000 Hilton Honors points for 6 nights of car rental with National Car Rental (150k Hilton Honors points, depending on who you listen to, is probably worth about $800. The 6 rental days at Christmas time would have cost me $1400, so I thought that was a good use.) and 20,000 Chase Ultimate Rewards for 3 inter-island flights.  That’s a total of 380,000 points.

When I was planning my vacation I had a very hard time deciding on hotels.  In some locations I had no choice if I wanted to stay with Starwood. For example, on the Big Island there is only one Starwood hotel, the Sheraton Kona.  Kauai and Oahu have several choices.  I debated and went back and worth before finally settling on my hotels.  In the end, I had vacation regret because I picked a few bad hotels.

In Kauai I decided to stay at the Sheraton Kauai because I could get 5 nights for 35,000 points – such a deal, or so I thought.  I could have stayed at the Westin Princeville for 50,000 points or the St Regis Princeville for 60,000 points.   It would have been a push to save enough for the St Regis, but I could have done a points and cash rate at another hotel and probably have had enough.  But I definitely had enough for the Westin, and that’s where the regret comes in.


The Sheraton

The Westin

The Westin

My stay at the Sheraton Kauai was less than desirable.  The hotel is older and the service is sub-par, but even more disappointing is the cleanliness of the rooms.  Not only are things old and worn, but there were bugs in both rooms I stayed in (I switched after finding the bugs in the first room) and things like the light switches were coated with dirt ( I took an alcohol swab and wiped the light switch in the bathroom, it was shockingly disgusting and I will probably have to clean every light switch from here on out at hotels because of this. Yes, I know it’s a little OCD.)

A Bug In The Bed

A Bug In The Bed

On one day while I was in Kauai I went up to the Westin for lunch and a tour of the vacation properties and then to the St Regis for a spa day and relaxing drink by the pool.  Seeing what the Westin and St Regis offered made me disappointed that I didn’t spend the extra 15,000 points to stay at the Westin.

Royal Hawaiian Bedroom

Royal Hawaiian Bedroom

I know that some people don’t care about the hotels and can sleep on the beach, and that’s fine too.  But some people, like myself, really enjoy the hotel experience and luxury and it’s just as big a part of vacation as the destination and activities.

So, the lesson I learned from this vacation is go with your gut and don’t choose the cheapest option just because it is the cheapest option.  If you have the points, and you’re planning a dream vacation, spend the points so you’ll enjoy yourself.   I know that after I build up my balances again this year and start planning the next big vacation (Africa if you’re wondering) I will earn enough to stay at the hotels I want to, or shorten the trip a little so that I can stay where I want to.

I had a wonderful time in Hawaii and enjoyed many of the hotels I stayed in which ultimately helped me to figure out that Sheraton just isn’t the brand for me and I need to save up for the Westins, St Regis and Luxury Collection hotels!

Are you a lux hotel person or are you just as happy at hostels?


7 Comments on "A Vacation Regret"

  1. We were in Hawaii around the same time!

    When choosing to spend more points or go for a cheaper hotel, there are potential downsides to both. You may feel like you “wasted” some points and could have saved or you may end up in a not-so-great hotel and have a not so great vacation. As long as I have enough points, I can always earn more points so spending a few more for a more luxurious experience is not a big deal. However, time is my one non-renewable resource as I work so hard the rest of the year.

    In Maui, I stayed at the new Andaz. No regrets there!

  2. @The Miles Professor – I feel like I was always an Island behind you! I wish I’d stayed at the Andaz. It looked amazing!

  3. If you’re going to Africa it’s time to save some cash as well… Most of the great places aren’t part of a chain.

  4. Thank you for your post about Sheraton in HI. We’re planning on our HI trip with my siblings in summer 2015. This is definitely something to think about. Bug?…. hmmm. No thanks.

  5. So sorry you’re suffering from “vacation regret”. I’ve fallen to the same disease in the past and even though it’s a first world problem, it sucks.

    BTW, as someone who can sleep on the beach…it’s still okay to want luxury. When I sleep on the beach, I pay $0 so it’s okay to expect nothing 😉

  6. The Deal Mommy | January 12, 2014 at 9:08 am |

    As someone who firmly has a foot in both worlds, I regret when I don’t get value for my time/money/points spent. If I’ve spent less and I get less, I’m ok with it. But in your case, basic cleanliness and lack of bedbugs is a given in a Super 8, much less a Sheraton. I don’t know that merits a regret as much as a refund and an apology.

  7. @GH, yes! That’s a big part of this year’s planning. Hotels will be expensive.

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