To Maui or Not to Maui?

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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.

Zoinks this is a tough travel age!

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.


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

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  1. I would say can the trip for this year. Being part of a family means compromise. If you go somewhere fun I am sure your older daughter will have a great time. Jet lag killed me in Oahu in September. It was worse than travel to Europe or even Australia for me. Having a out of sorts toddler for a week does not sound like a great vacation.

  2. Can you leave a day early and do an overnight at a West Coast City before the Alaska flight to Maui? Also Alaska flies from Seattle, Portland, Oakland, San Jose, San Diego to Maui (plus a few seasonal ones), did you check availability for all that? If AA doesn’t work, see if you can do Delta using KE miles. Don’t give up yet.

    • Considering that if we keep the trip. Availability for everything is pretty poor, but splitting it up does have advantages for sure.

  3. My son is a month younger than Little S and we’ve been to Maui three times with him already, I have a field trip there in March and are planning another family trip in July (from the West Coast though). One of those times we flew first class on Alaska (with a lap child). The seat was very uncomfortable in my opinion. My back hurt after that flight and I am not flying Alaska first class again. I am telling you this in case it helps you decide that economy flight on Alaska is not much of a step-down from first on Alaska, so if losing first class gives you better routing, go for it.

  4. We love Maui, too, but I’m not sure if I’d go under those circumstances.

    My children are MUCH older than yours, so it’s funny that we just ran into a similar situation. Hubby and I planned to take our 23yo to Spain. We booked the perfect 1st class tickets far in advance (very hard to get to Europe on AA without using BA and paying fuel surcharges!) and then something *really* important for our 20yo came up. Of course it’s impossible to change our dates to Spain now before the tickets expire, so I need to redeposit the miles and pay the fee and hopefully book later. It was tough to tell 23yo that she can’t go to Spain because of her brother, but she took it gracefully. 🙂 We offered a shorter trip to Mexico City in consolation so we’re looking forward to that.

    All that to say that parenting when they are adults remains both a joy and a challenge sometimes. 🙂 Good luck on your decision.

  5. Would you consider splitting the trip and stopping for a night on the West Coast? We took our two girls (then six and four – granted, easy-peasy compared to 20 months…) to Maui from Atlanta two summers ago and stopped in California both ways, San Francisco on the outbound and San Diego on the return. We flew out early enough to have some time in SF to explore and adjust a little, and our overnight from Maui landed in time for us to sleep really late in SD before enjoying the incredible pool at the Hyatt Regency Mission Bay for what was left of the day. It was really a perfect way to get there an back without the craziness of an entire day of travel, plus we had a little time to explore cities neither of my girls experienced.

    My first inclination would be to cancel the trip and try again next year. I had non-sleeping babies and totally remember the exhaustion. It’s the reason I stopped at two kids. 🙂 BUT there is something really wonderful about overcoming that and finding the sheer joy that comes with being in a beautiful place with my family. So I say go for it!

    • Stopping on West Coast on outbound is certainly on the list of possibilities for a night. Congrats on 4 and 6 – great ages!

  6. Ditch it. At this time of our lives travel is about pleasure and not pain. Your daughter will understand and if you provide her a great alternative she will forget about Maui in a second. BTW, although I love Maui I was a bit disappointed when we were there last year since the island is more and more becoming a little Honolulu. Don’t get me wrong since I still love both but I prefer the old Maui that you can still find if you go to Kauai and Big Island. Maui is now full of constructions, condos and stores everywhere. Traffic was terrible and you have to find your way to relax. BTW, I know you are loyal to Hyatt but I cannot understand all the hype to the Andaz Maui. The hotel is not worth in my opinion since the service is bad. I would rather stay at the Four Seasons while in Maui or go out of the busy Wailea and stay at the Ritz in Kapalua.

    • Totally agree travel should be (mostly) fun and not a total PITA. Re the Andaz is was pretty solid at first, but I have heard more mixed things in the last couple of years.

  7. Sounds like the issue is getting to Maui. But after arriving it should be fun. I agree with the post about flying to the west coast the day before and overnight, then continue the journey to Maui the next day.

  8. As a 63 year old grandma and educator, I have a suggestion you haven’t mentioned. Why don’t you and little C go by yourselves? Over the years we often did this with our children where we did ‘one on one’ vacations and it was great. In fact, yesterday I planned a get away with just me, one of my daughters and her daughter. I am ALL ABOUT FAMILY and we do a trip every year where all of the generations are together, but it is also good to spend specific time with each child. C is a great age for this and you would be making memories that she would never forget. Also you would be able to put a lot of cancelled miles and hotel points back into your accounts and you could use them for an entire family getaway in a few months for a long weekend. Like you, I am a lover of Hyatt Lost Pines for family getaways so perhaps you could use your Hyatt points and suite upgrades there. Just think about it…….and if you decide against this idea then I would cancel this trip as I think you are biting off more than you can chew. You are a great mom Summer, so no matter what you decide your sweet family will continue to thrive.

    • Aw thanks! I actually have a trip just with C this winter to ski. Very much looking forward to it, but probably can’t pull off two in back to back months.

  9. AA has an obscure rule that gives you 18 hours instead of the typical 4 hours for a stopover before the flight to Hawaii as long as you are on AA metal. Great to make an overnight stopover on the west coast.

    As best I can tell the award engine doesn’t take this into account. It needs manual intervention to price out properly.

  10. Like others said; because of the schedule change, I’d split the outbound into 2 days — keep the original F flight from the West Coast to Maui and spend the night in a hotel near the airport.

    And maybe make a back-up plan so you can cancel the Maui trip if you’re still not feeling it when the time is closer.

    • Sadly our trip is already borderline too short so I really need to bump it a day longer more than a day shorter. Otherwise really like the idea. Will keep playing with it.

  11. I say go to Mexico. If swimming and playing are the main objectives, Mexico can fit that bill without the 17 hours in travel. Hawaii is gorgeous and awesome and we promised our daughter a trip there for her 10th birthday to celebrate double digits because its such a long flight and time change. But that’s a hard trip even for Little C to go and then come back and go back to school without some time to recoup. I agree that being a family is all about compromise and she’ll understand if you promise a trip to Hawaii in the next couple of years. I say Mexico for the win.

  12. How long are the “super long” and “super tight” connections? You’ll have lounge access, so any long connection shouldn’t be that big of a deal. If the tight connection isn’t one you’d likely miss (not like you should have to deal with snow or something with the cities you are flying through), then I’d definitely do it.

    We’ve been doing Hawaii almost every year with the kids, in coach *gasp* for a few years and our youngest is 4. Our normal trip to Hawaii normally involves 2 connections because we are in a small market and can’t get direct to the west coast.

    Hawaii is so much better than Mexico in so many ways.

      • Can the outbound – that’s terrible! I’d do just about anything to keep the trip but improve the outbound. We are going to Maui for Spring Break in a couple of months too, flying from DSM (tiny market). This will be our 3rd Hawaii trip, and our kids are 6 and 3 – the 1st trip, my daughter was just shy of her 1st bday and my son was 3, then we went again when youngest was 2y+3mo, and eldest was 5. On both of those trips, we flew in 1st class from DSM-DFW, overnighted at the Grand Hyatt DFW (love!), and then got on the morning nonstop to OGG. It’s a looong direct flight, but by splitting the trip and having the good seats up front, it was honestly pretty easy. Wayyyy easier than some of our shorter flights have been.

        This trip will be the first time we aren’t flying AA in first. Instead, it’ll be United, in economy. Kinda dread the economy aspect, but it isn’t awful. Usually flying from DSM would mean hellishly bad setups with at least 2 stops and longish layovers. Instead we’ll have just 1 nice stop in DEN and be on our way to OGG. At just 6.5-7.5 hours, I figure my hubby can tough it out with the lack of legroom. If you could get something similar to this for yours, I’d be pushing your hubby hard to suck it up in economy.

        For us, Hawaii is magical. We’ve been to Mexico, Aruba, and Costa Rica x2 in the last 3 years, but none of them have that magic. My vote is to go for it if you can fix your outbound. But with the outbound as it stands? Hells no.

  13. I would cancel the trip. We took our one year old daughter to Maui and regretted it. She was such an easy traveler when she was 6months old and slept the whole time when we took her to Europe. So we thought it would be the same in Maui. Unfortunately, she would not sleep, even when we rocked her in our arms. The only way she slept was when we rocked her in a hammock. She woke up every hour in the night. Needless to say, we were dazed and tired the whole “relaxing” vacation. I would recommend visiting somewhere you can put her in a stroller and fall asleep while you sightseeing.

  14. I think don’t give up yet – if this were all planned in economy and standard rooms I might feel differently, but given everything that had to fall into place it seems a shame not to use it. I also agree that it might be worth considering not taking the baby and downscaling to a 2 person trip – either you and little C or better yet you and Josh!

    @Santastico – I agree with you about Maui. It’s still beautiful in places but don’t go there expecting Hawaii of old.

    • I don’t think I could ask anyone to keep her for us the week school is closed while we dash off to Hawaii, but I do have just a trip with the older for a long weekend this ski season. Having the right availability does make it so much harder to just can!

  15. Just did Maui and Oahu with a 17 month old and a 38 month old in May. Flew from DFW. Book 330 days out and the airline STILL split us up so that was hard being away from my hubby and our lap child 17 month old for the duration of the flight but it wasn’t THAT bad. None of it was as bad as I’d feared.

    There was a little jetlag but not as bad as I thought it would be. We were up around 6:30 local time so not too bad.

    I was just like you thinking OMG what have I done!!! I booked it when our youngest was a sweet and easy to please 6 month old. As the trip got closer I was petrified for all the reasons you state but we had a great time and never once regreted our choice.
    Go for it. I always seem to regret the things I don’t do more than the things I do.

    • Thanks for sharing! Yeah it could be totally worth it if we do it…or it could be one of those trips that I regret pushing forward with (though most of those were work related in some way). Crystal ball, where are you?! 😉

  16. If your number 1 reason is that your daughter wants to …. that’s an easy one to nix.

    Kids that age love:swimming, playing, and swimming, as you mentioned. They do like the ocean, but are oblivious to which ocean. Why not Florida or Caribbean?

    • Well the downside of raising a traveler is that they do know the difference between Hawaii and just a beach. We’ve been talking about it for well over half a year at this point. So, she would be fine no matter what obviously, but to her there is only one Hawaii.

  17. Tough decision! My family went to Hawaii in 2015 when my youngest was 4. She had a hard time with the time change and was up by 4 a.m. and asleep very early for almost the entire week. But I say, go for it!

    • I took my oldest daughter for the first time at 3 and she did pretty well too. Just not sure if the toddler will be that adaptive. 4 is a great age!

  18. Connections are death with infants. After a harrowing short hop that followed a TATL I longhaul I now always include an overnight at every connection. If you do go as ticketed I bet you dollars to donuts it is the DFW-IAH flight that gives you the most trouble.

  19. Summer, it’s clear you are very concerned about if you want to put yourselves through what might be too grueling of a travel experience. Yes, it might not be a piece of cake. But, you are young. You can do this. And, you have created a superb class of service for your spring break’s flights and hotels that most people can only dream of. It’s Maui!! Embrace this chance to be in Maui, which for so many is only a pipe dream and will never be realized. Dig down deep and continue to visualize all the beautiful colors and fragrances that Maui will offer you. No doubt in your life you have extended exhaustive energy on tasks with far less pay off. My creed is, never put off Maui. Go while you have the chance.

    • Thanks for that. I know we are so lucky to even have the chance to go to Maui. I hate to have such a great opportunity and be too tired to really enjoy it, but Maui is special for sure.

  20. Were there better flight options going to another island? We needed to get home LIH-DFW and couldn’t find anything so we are now doing an overnight (overnight wasn’t necessary we just wanted to try another resort) at HNL because we are flying a 32 minute flight on Hawaiian Airlines that we booked with AA miles out of our 2 girls accounts but booked mine and my husbands as intra-Hawaiian Roundtrips on United to get the free leg. We will be doing DFW-YVR on Labor Day now.

  21. Oy… we had just a horrendous experience with United when our daughter was 4 months old from LAX to the Big Island via San Francisco, which is notorious for delays anyway but there was a mechanical issue on the outbound flight, so we missed our connection. United flew is back to LAX to catch a direct to the BI but when we landed, the flight was delayed until 10pm later that evening. Luckily, we live in Los Angeles, so we just went home but there was a couple from D.C. and they had been trying to get to Hawaii for over a day. The evening flight rolls around, flight is booked, we pull back from the gate, take a ride around LAX, go back to the gate and they told us the flight was canceled! We didn’t get to Hawaii until the next day, we demanded United book us on Delta which they did but we spent 2 hours getting it all straighten out.

    The return flight, again through SFO was even worse. Let’s just say we are lucky to have friends in San Franciso because we would have been homeless with a 4 month old due to all hotels being booked because of a conference in the City. After this experience, we have avoided any connections – were going to try it going to Zurich (again through SFO) but there is a 4.5 hour layover – well just go to the lounge. However, it’s taken us 5 years to get over this nightmare.

    The way the flights are – I’d rebook for a direct in economy plus or something, flying first isn’t worth all those flights just to get to Hawaii with a 20 month old, this was the worst period to fly with our kiddo. I’d be stressed out.

  22. We’ve had similar conversations in our home. Having done Hawaii several times with our kids as they got older we started mixing in Mexico (Cancun and Cabo) as well as Phoenix. Our kids are the happiest when they have other kids to play with around the pool/beach etc. and they don’t care (can’t tell) whether that pool/beach is in Hawaii or in Mexico. Mom/Dad can certainly tell where we went once the credit card bill arrives (even though we also use points/miles for all the flights and hotels). Especially while the kids are sub-teen I’d suggest checking out places based on the kid-friendliness of the pool area. We did a trip to a Hilton in Phoenix (don’t remember the name) where the cost was incredibly low due to using Avios for flights and easily-available cash+pts (was maybe a 3-star hotel) but the kids would say it was one of their favorite trips because it was the type of place that’s full of kids (as opposed to some of the nicer places in Hawaii). As for Mexico, you can usually get saver awards if booking well in advance but later on the cash prices start to look like Hawaii. And, both we and the kids love the all-inclusive aspect plus the service is so much better versus Hawaii. If booking on shorter notice when there’s no saver space and the cash prices are higher, take a look at the vacations for your trip (likely UA, SW or AA for you) as the discount on the air portion can be substantial. We’ve gotten to where we are more frugal on the family trips (and focus on the family time) while splurging when it’s just mom & dad on the trip !

    • For sure. I’d love to overlap a trip with kids she can play with, but so far haven’t convinced anyone to join us to an easier destination. That would tip the scales though I think!

  23. We did ORD-MSP-HNL-OGG r/t in November in Delta One at the saver levels in first. We stayed 5 nights at the Hyatt Residences and then moved to the Regency next door for 3 nights w/ a suite upgrade to a Lahaina suite that overlooked the Luau. Although the D1 first class was nice and the Hyatt’s were both very nice, it was a long trip and the extra stops and layovers really took their toll. I don’t think we really recovered and felt on a normal clock until about our 5th day….and our party was two 35 yr olds in pretty good shape.

    I think sometimes finding that perfect redemption of US48 to Hawaii in 1st class or suite upgrades convince us the trip will be wonderful. If I had it to do over, I’d have gone to the Rivera Maya or somewhere closer.

    I think you’ll have a fun time if you go, but don’t feel bad if you deceide to cancel

  24. No, I would not take this trip the way it stands. Wayyy too many segments and chances for things to go wrong. I might consider it for a lengthy two week trip, but not for a 5-7 night trip. I suspect you wil move forward, though. I would try for IAH-LAX or SNA or SAN and spend the night at a hotel with fun pool then continue on a non-stop to OGG the next morning. Good luck!

    • I really have no clue what we will do. I call it an even 50/50 right now. Agree that stopping on West Coast could make getting there easier.

  25. You are already expecting grief and it is two months out. I don’t expect that you will be feeling any better about it two months from now and just the anticipation of the grief you will go through would make me pretty miserable and pretty much anything that goes wrong will likely reinforce that feeling.
    From Houston, I would substitute a trip to the Andaz Papagayo. You have a number of ways to get to Liberia, including nonstops with United and Southwest (so award space is a decent possibility on united and pretty much guaranteed on Southwest). The pools are great and the beach at the beach club is also fantastic, especially for little ones, as there are next to no waves. Even if you can’t get a suite, the regular rooms are very large (we put two rollaways in one of the rooms, so all 4 of our kids stayed in one room and we stayed in the other).
    The only issue may be availability, although it seems to be available for at least some spring break weeks.

      • I would do it with kids. Like I mentioned, the water is perfect for kids, the kids club is pretty decent, and the rooms are large enough for kids. Not sure if it is still the case, but when we were there, the kids ate free in one of the restaurants as well.

        • My kiddo loved Andaz Papagayo, the Kid Club is fantastic and the General Manager has young kids as well. My daughter and his daughter got on fabulously. And the club leaders are really great with kids – I liked that they put a lot of thought into the place.

  26. It’s booked. GO!!!

    “Be bold and courageous. When you look back on your life, you’ll regret the things you didn’t do more than the ones you did.”

  27. We’ve been taking our 5 kids too Maui ever since the oldest was 1 year old. When they were all really small, we would fly to SEA. Stay overnight at the Embassy suites by the airport…free shuttle and breakfast, on the water and good plane watching too!. Then fly United straight to OGG. Always worked out well for us. The jet lag was never really a problem. We would always stay at least 10 days and after the first day or two, the kids were back to their routines. We alternate between Maui and Mexico. But Maui…with the whales and the culture and the kind people…it’s just magical.

  28. Wait, you have to go during “Spring Break”, because otherwise little C would miss a week of First Grade? What are they going to cover during that time, the letters m, n and o, and thus she will never learn to read? Reschedule at a date with better availability, she will cope with missing one week of school with no problem at all.

    On the other hand, you have a ski trip planned for just the two of you the month before, and are concerned that Little C will be heartbroken to not go to Hawaii, vs “just a beach”, the following month? Oh, how I wish my childhood had been so privileged. This doesn’t just sound like a “First World Problem”, it sounds like she is trying to keep up with Malia and Sasha’s vacation schedules. 😉

    Finally, starting out already exhausted, on a 20 hour travel day, with a 20 month old who isn’t even sleeping well at home, doesn’t sound like a great idea at all. 20 % chance it turns out well, 80 % chance it becomes the vacation from hell. I just don’t like those odds. But that’s just me.

    Then again, if anyone could pull this trip off, as scheduled, it would definitely be you, so there’s that in your favor. 🙂

    • I am okay missing a day here and there but a full week at once just pushes the limits of my personal comfort. That’s nasty letter territory at least. She’d catch up fine but school would probably not be happy with us. She would also be fine if we don’t go, but it I know it does matter to her because we have always loved our Hawaii trips so that makes it harder for me to just can as opposed to a trip she doesn’t feel strongly about one way or another.

      • Really? A nasty letter because your family is out of town for a week? Yes, if you are missing a week or two every month, just because you don’t want to bother to get her dressed and ready to in the morning, that would be nasty letter territory.

        Often if it’s a public school, the school gets funded per student per day of actual attendance by the state. But if they are going to complain over missing 7 days of funding for one student, that’s their problem IMHO.

        • I believe missing 3 days (or any part of 3 days) in a four week period triggers a truancy letter. Additionally you must attend 90% I think every 9 weeks. She will miss two days that 9 weeks. Another week would tip her below 90% for sure. I think anything over 4 days in 9 weeks tips you under.

  29. Did you consider Houston to San Diego, spend the night, then San Diego to Maui? Virgin is awesome! We spent 30 years going to Maui as a family. My kids are grown now, but have wonderful memories!

  30. Flip a coin. Head Hawaii. Tails Texas. See how you feel after the toss. You will probably be disappointed or relieved. Then make your choice.

  31. Go on a Disney Cruise from either Orlando or Miami. You will have plenty of family time as well as alone time. They are very family oriented and a lot of fun. Save Hawaii for another day when both kids are old enough to swim and then try he Grand Wailea. I’d stay there with younger kids. I’m sure you know that your daughter will survive not going to Hawaii for her 1st grade spring break. Think about the down time that YOU need to continue to be the mom that you are to your kids. It’s more about the quality time you spend together than the destination. Also, the family dynamic at any given time does dictate how we spend our free time. Trust me. As a mom of 4, i have a tremendous amount of experience with this. And we have extensively traveled all over the world, as a family, and partial family… I say shelf it for now. Upgrade certs be darned. You’ll do what’s right for your family and whatever that may be, safe travels and enjoy.

    • Even though we have never cruised I actually was looking at that! Sadly the only ones on our dates seem astronomically expensive compared to the others, but I love that idea and will be filing it away for use in the nearish future as I think they are at a good age for that (other than all staying in 300 square feet or less!). Wish they sailed from Galveston in March!

  32. How are you using 2017 Hyatt Diamond Suite Upgrades already? They aren’t awarded until end of February 2017, and current suite upgrades expire then as well. Am I missing something here?

  33. I’d say go, and make a list of all the top amazing advice you have given folks over the years about traveling with an infant. Then as you travel, check off all the advice one by one in a post or posts on Twitter (hubby might have to help…) and you will see you might get there easily afterall. On top of that you will have great material for the blog and you all will probably enjoy it too!

  34. Advise from others will be of little help in this scenario. You know your family. As such, you know what to do and why it’s the best course of action to take.

  35. Just back from the Big Island with our two year old, had some good times and bad, including driving her around at 2am and then sleeping in the rental car. I’ve given up on vacations being relaxing with young kids, there’ll be parts that are good, parts that are tough. Good luck!

  36. Not a tough decision. Chill out and quit stressing or you’ll drive your kids nuts. Kids will adapt. Parents can suck it up. People in airplanes can deal with it if it gets nasty. Comparing Maui to Mexico in the same sentence has no logic, trust me. Once you land, get off the plane and feel the trade winds, all the hassle goes away. And the people who post here that don’t get it, well, they don’t get it.

  37. We went to Oahu when our daughter was 17 months and it was 2-3AM wakeup calls every morning until the very last day when she slept until 5 – hallelujah! What do you do with a fully awake one year old at 2 AM in a hotel room so she doesn’t wake-up everyone else??? I remember as soon as a crack of light came up outside we’d go for a long morning walk so everyone could sleep. We still had a pretty good time but I came back tired. Our recent trip to Maui with a 4 and 8 year old was way more relaxing.

  38. I grew up in Hawaii and go back with my now-5-year old multiple times a year (all of my relatives are still there), so of course I’m biased, but…I vote for going! I agree with others who commented that Hawaii is not what it used to be–so much has changed since I was a kid there–but the people are still lovely and laid back, the trade winds still carry the scent of flowers, you can still be surprised when you’re out for a swim and a green turtle decides to surface near you. It’s a paradise, like Mexico is. We fly with Alaska from Oakland or San Jose because the airports are smaller and less crowded, and 80% of the time we’ve been able to upgrade to first upon check in (for $100, I think). I agree with one of the commenters, though, that Alaska first class is not a huge step up from economy, but the 2-2 seat configuration in first is nice for a family of four. Good luck either way! And also, thanks so much for your alerts about those super-low fares to Europe! We’re spending spring break in Amsterdam thanks to your tip!

  39. 20 hour travel day is INSANE

    You might as well go to the Maldives

    I vote for a night in San Diego or LA

    The renovated Hyatt Regency LAX is cheap and caters to diamonds

    $10 Uber ride to the beach for a few hours of fun and THEN back on the plane

  40. Much prefer Hawaii to Mexico (we visit Cabo every year and Hawaii almost as much) but just does not sound relaxing or IMO really worth 20 hours in transit for a week (not to mention the redeye back). From Texas you are blessed with shorter flights to Caribbean and Mexico so get a nonstop and save Hawaii for another time when hopefully you can get one-stop service. From CA we do the opposite (Hawaii & Mexico but no Caribbean) and Europe only if we have 1.5-2 weeks.

  41. We did our first trip as a family of four to Kauai when our youngest was 19 months old… was fun, but a little challenging and not that relaxing. We only had to fly from SFO, but the flight over was nearly five hours of pacing the aisles with her. It was fine when we got there, but we were still definitely in the toddler stage in terms of dealing with mealtimes, naps, etc. In contrast, it felt much easier with an earlier trip to Hawaii when our oldest was nearly 3 years old and she was our only child, so the timing makes a huge difference.

    My suggestion is to either stick with the trip and break up the outbound flight with a stopover on the West Coast, or postpone the trip for a year or more until your youngest is a little older.

  42. Remember it’s a 20 hour travel day if nothing gets delayed. You still have to land in Maui and pick up your rental car during one of the busiest times of the year. Then also check into a hotel that may be extremely busy. Honestly, it’s not worth it IMO to lug a family of 4 only to be exhausted with a baby who doesn’t sleep well. Both my babies never slept well and being in hotels usually made it worse. I would just reschedule or change locations (even though the clock is ticking for Spring Break). It’s so much easier to travel and less stressful when you don’t have to bring all of the extra baby items. Either way, I hope you and your family have a wonderful Spring Break.

    • Thanks and totally agree. The 20 hour + travel day is not even on the table. Still exploring ideas, but simpler is better is the theme of 2017.

  43. Very interested to see what you decide to do. We have a similar trip planned for June with a what will then be a 12 month old who currently doesnt sleep very well or at all. We are very much on the fence about the trip and after many months of sleep deprivation are leaning toward cancelling. Traveling has always been a big part of our lives so its sad to think that we would let a child dictate our lives but I can only imagine how miserable a flight to hawaii would be with a fussy baby.

    • I am 98% that we are not going to Maui this spring break…or likely this year. I found a way it could work with staying on the West Coast on the way out, but my husband is pretty firmly in the “not worth it” camp. I totally understand his point of view, and since I was just 50/50 on it, having him be pretty firmly against at this point will almost certainly tip the scales into not going. It might have been worth it once we got there, but honestly it also might be WAAAAAAY more exhaustion than it is worth this year. Maui will still be there in a year or two when our littlest is in a better stage to go. We haven’t officially changed anything yet, but Mexico or Grand Cayman are looking like much safer bets right now.

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