Skip to content

To Maui or Not to Maui?

Jan. 02, 2017
7 min read
To Maui or Not to Maui?
This post contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products. Terms apply to the offers listed on this page. For an explanation of our Advertising Policy, visit this page.

In spring of 2016 I booked our 2017 family spring break trip to Hawaii using airline miles, hotel points, suite upgrades, and more. I was pretty excited with how it all worked out and that we were able to get the availability to line up. I figured (hoped) that by the time of the trip we would be at a point where that big of a journey wouldn't be too terrible of an idea. Our oldest daughter would be nearing the end of first grade and our second daughter would be about 20 months old. By that 20 month mark with our first daughter she was pretty conversational, sleeping just fine through the night most of the time, and travel was starting to get much easier than it was in the 9-18 month "hardest age to travel" range.

I told myself not to worry, that the trip would be fine!

Fast forward many, many months from the time of booking to now and we are just under two months out from our spring break trip to Maui I'm having serious second thoughts. Things aren't terrible here, but sleep still is not a given, we are still tired more than not, and while the little one is picking up new words on a regular basis, she isn't conversational enough for me to trust that she can understand what is happening next on a long travel day and communicate all of her needs with words.

I knew Maui wasn't a super easy destination to reach, so I put a bunch of thought into the best way to get to Hawaii and back with a young kid, and ended up using 40,000 American miles each to fly Alaska first class to Maui, and a few more miles than that to American first class Maui - Dallas - Houston on the overnight return.

The outbound was always going to be rough as it is Houston - Dallas - West Coast - Maui, but with spring break travel dates that is as good as I could come up with. However, a schedule change happened on our outbound American awards that made a long travel day even longer and nastier with one super long connection and one super tight connection thrown in for good measure. I've tried to have American put us on easier flights on our date or even the day before, but they are just simply full, at least in first. They may be able to make some slight alterations to one of our flights, but this isn't one of those times where a schedule change will work in our favor and enable us to unlock much better flights.

A very long travel day with three flights, a relatively big time change to get to Hawaii, two hotels booked while we are there, and the reality that we will probably be tired before we even start the journey, and I'm no longer dancing the hula thinking about the trip. Instead, I'm starting to tip toe around a back-up plan. We have had great trips to Mexico the last two years, and I'm tempted to just try and go 3/3 with that logistically easier and much closer plan, but it is just not as simple to just throw in the towel on Maui as we have done to some other overly ambitious plans.

Reasons to Keep Trip to Maui:

  • My oldest daughter really wants to go. I mean really, really wants to go. She has had to change a ton of her day to day life with the arrival of her sister, and for her to lose a trip to her favorite spot largely because of her sister just doesn't feel right at this point. Of course we could make up some other stated reason for the change, and would be fine in the long run either way (obviously - we are talking very first world issues here). Still, knowing how much she is looking forward to a return to Hawaii makes it much harder to cancel.
  • I won't be able to just recreate this trip later. Not only was it a small miracle I got the award availability I did in the first place, but I used Hyatt Diamond Suite upgrades that I probably won't have again. We have suites lined up at both hotels in Hawaii that may very well be out of range in the foreseeable future for us.
  • While some of the logistics of the trip sound exhausting, we have always had an amazing time in Hawaii. Our planned on-the-ground hotels and activities of swimming, playing, and swimming again sound perfect for us. I hate for us to miss out on that just because I'm apprehensive about the travel time and time change.
  • At this point so close to spring break being able to get saver awards, low priced flights, etc to other beachy destinations is not all that likely. I will be giving up a trip booked largely on miles and points for one that probably isn't nearly as good of a deal from that perspective.

Reasons to Ditch Maui

  • As it is currently booked, there are about 17 hours of travel to get to Maui, not counting getting to the airport in Houston or from the airport to the hotel in Maui. Factoring all of that in, It will be about 20 hours of travel with a 20 month old just to get to Hawaii. Oh hells no.
  • To keep the trip I will have to book a new outbound flight, and American doesn't seem to have any options that are much better available to us. This means I have to start over on our outbound flight search which probably won't come cheap unless I get very lucky. There are currently no saver awards that will work, so I will likely have to buy new tickets to Hawaii. Because paid first class seats to Hawaii are out of my price stratosphere, our new seats will most likely be in economy, and not first as originally booked. This means my husband will be none-too-pleased since that is beyond our agreed upon radius in economy.
  • Our little one wakes up early already on a good day, and if you add in the time change she may easily be waking up at 3 or 4AM the first several days in Hawaii which will not make for happy campers.
  • It just sounds intimidating, not relaxing. I mean, the swimming, playing, and eating in Maui sounds fun, but the trip as a whole just sounds like a lot of work. I know we can pull it off, but since there are no work obligations at all tethering me to this trip, should I pull it off just because I can?

As you can tell, I'm really on the fence with this one. I love Hawaii, and if I could wiggle my nose and transport us all there I know it would be great. But, I know that the trip as booked probably is too much work for the reward. I have to make changes at least to our outbound flights no matter what, but I'm just not sure if I should keep investing in a trip that may be another right trip at the wrong time, or if I should just pull the escape cord now and start over. On the other hand, this may just be a case of logistical cold feet and with some new outbound flights and over two more months of growing, this could turn out to be our best trip yet.

Sign up for our daily newsletter

Spring break on a beach sounds perfect, but I'm just not sure what sort of Aloha to say to Hawaii this year.

Top offers from our partners

How we chose these cards

Our points-obsessed staff uses a plethora of credit cards on a daily basis. If anyone on our team wouldn’t recommend it to a friend or a family member, we wouldn’t recommend it on The Points Guy either. Our opinions are our own, and have not been reviewed, approved, or endorsed by our advertising partners.
See all best card offers