We Decided to Say Aloha to Hawaii

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A few weeks ago I posted about my indecision regarding whether or not to go forward with a planned spring break trip to Maui, or (again) decide that we bit off more than we want to chew, and scale our trip back to something much closer and easier to get to with our two girls. Most of my hesitation came from taking a hard look at our very long itinerary to get there (that had been made worse with an airline schedule change), and the reality that our youngest is still in the “hardest age to travel” range.

Zoinks this is a tough travel age!

When I wrote the post, and in the days after, I was strongly leaning towards not going to Maui. It was just too far. Too many flights. Too big a time change. Too much effort. Too high of a risk of exhaustion and meltdowns. It didn’t help that when I wrote that I was coming off winter break and the girls being home for two weeks, which is fun, but also sort of a challenge when you also work from home.


Trying to Put Together an Alternate Spring Break Trip

When I realized Maui may be overly ambitious, I tried to put together an alternate trip to somewhere like Mexico or Grand Cayman that we could easily reach with a short-ish nonstop flight. I mean, I really, really tried. However, this close to spring break, the reality was that no matter what I tried, I was looking at having to spend way more than I wanted for any decent looking alternatives. The best vacation activity for my girls at this age is swimming somewhere warm with a great pool, so that had me stuck looking at the same destinations on the same dates as everyone else.

The cheapest alternate trips I could find for our dates that looked like a good fit for our style of travel would cost us $2,500+ some miles/points for a 3-4 day trip that really should only cost a fraction of that amount. That is what happens when you are booking a trip close-in to a peak travel week.

I would be trading under $1,000 in cash expenses with first class flights + hotel suites booked at good award levels in Hawaii for likely 3x that cash amount for standard hotel rooms and coach flights to somewhere like Mexico. I love Mexico, but I love Mexico on a deal, not at full-blown retail price on a peak week.

The sticker shock for other spring break trips made me pause and really think about what was best.

Ultimately I decided that spending close to $3,000 for an alternate 3-4 day trip was insane, and certainly not the way I travel. I decided we were either going to Hawaii with roughly what we had booked, or we would drive somewhere like the Hyatt Hill Country Resort and do a 2-3 night stay there with no airfare costs and a low cash + points hotel rate.

We Were About to Say Adios to Maui When….

I had all but accepted we were headed to San Antonio instead of Maui when my husband called one afternoon and said “he had a change of heart”. He decided that the effort to get to Hawaii with the girls was worth it, and he was all-in on the trip to Hawaii. What?! 


I had my reservations about making the big trip with our toddler, but he really had reservations. However, with him fully on-board, the game changed. You can do anything you set your mind to, and with both of us in the right frame of mind to make it work, it could.

I mulled it over a few more days and and then called American to see what they could do about our flights since the schedule change had left us with just a 40 minute connection in Dallas, and a six hour connection in San Diego. I knew from extensive searches online that there were no other saver awards available, but I punted it to American to fix the problem. A 40 minute connection at a large airport with little kids when you have to wait for your stroller to be off-loaded at the gate is just a misconnect waiting to happen. On a busy spring break travel week, that could be a phenomenal problem getting all four of us rebooked on something else the day of travel.

At first the agent I was working with over the phone resisted and simply kept coming back with “there is nothing else available”, but when I pushed enough and specifically asked them to see about award space being forced open on a flight that wasn’t so likely to misconnect, they ultimately did.

Our flights still aren’t great, but we have a few hours in both Dallas and San Diego, instead of being insanely rushed at one and sitting at the other for half a day. In this case, that was the best I could get without spending $1,500 – $2,000+ new flights. Our travel day to Hawaii will probably not be a very fun day as it will be around 4AM to our bodies by the time we reach the hotel in Maui…and that is if nothing really goes wrong.



After that long travel day we would be in paradise. I can’t think of a better destination for both the adults and the kids in our family than Maui. The pool, the splash area, the weather, the play bridges, the slides, the food, the drinks, the suite, the club access, it just is a perfect destination for us….just a long haul to get there.

Minimize Impact of a Long Travel Day to Hawaii

To try and minimize our exhaustion and the impact of a really long travel day, I am doing a few things proactively to speed up the time from wheels-down in Maui to heads down in the bed.

  1. We will skip a car rental the day we land and instead schedule car service or similar to take us immediately from the airport to the hotel. The last thing we will want at 11PM local Hawaii time will be a car rental process. Maui Town Car looks like a potentially solid plan to get us to the hotel.
  2. Communicate closely with the hotel to make sure the pull-out sofa bed is prepped and there is a crib in the suite when we arrive. That process can easily add an hour to bedtime when it doesn’t go smoothly, so I have already gotten in touch with the hotel about those requests and will stay in touch leading up to our arrival to try and make sure everything is ready for immediate ‘night night’ when we arrive.
  3. Schedule a nanny for a few hours the next day. We aren’t traveling with a Grandma on this trip, but if we can schedule a nanny or babysitter for our first day full day in Hawaii, then we can relax a little knowing that we will have a chance to take a nap the next day. Exhaustion can be a mind ^@$@# when you don’t know if/when you will get a chance to sleep, but if we know there are some extra hands for the little one the next day so that we can take a nap, it will help both our exhaustion and anxiety on the long travel day.

I am also looking at all my old photos of Maui with the family and collectively we are getting excited and geared up for the trip. The more we can focus on why we are going, the more likely we can get through the long travel day with minimal drama.


Let’s be serious…stressing out about a long travel day in first class to get to Hawaii isn’t exactly a “real problem”. It may be stressful in its own way, but it isn’t actually something to stress about, it is just something to plan for. It’s always possible that unforeseen events will derail our plans, but at this point we are going ahead with saying Aloha to Maui for spring break and I can’t wait!




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  1. I Am sure you guys will have a great time. BTW, while I like Mexico (don’t love it) I find travel to their beach areas extremely overrated. I was able to take my family to Greece last summer for the same cost (miles+points+money) I would spend to go to Mexico. No way!!!!!!

      • Check “The Romanos” resort which is part of Luxury Hotels and Resorts where you can redeem SPG points. It is a Category 6 but if you stay 5 nights one night is free and you get an amazing breakfast plus 1/2 board. The hotel is simply unbelievable for kids and adults as well. We used Delta miles for our family of 4, rented a car and had a great stay. Best vacation ever.

        • That place looks awesome! How did you book a room for 2 adults and 2 children with SPG points? Every time I search for availability for my family of 4 it shows only crazy expensive suites.

  2. We’re heading to Maui in May with our 18-month-old, so totally understand the stress part of an otherwise very relaxing trip. 🙂 Any tips or suggestions on getting a nanny or babysitter there?

  3. I have an 18-month old and a 5 year old. I’ve debated the flight from DEN but just can’t see it. The longest trip we’ve made lately is 3 hours (SAN). I believe your timelines are accurate for the ages to travel. I don’t want to miss out on these baby years but there are so many great travel deals out there right now. For example, yesterday I saw flights to Paris to just drool over but a 13+ hour flight with an 18 month old would be insanity. So I will wait and enjoy the baby years as I’m sure more deals will be available. Not to mention I will just stash more points away to take an even better trip!

  4. @Mary Babies are much better at adapting than you think. I took an 18 month old there and a 3 year old and the kids did fine. I have 3 now and one is a teenager. The teenager doesn’t want to miss school activities to travel the world. The other 2 would be happier going to grandma’s house to play Wii with their cousins. They’ve traveled a lot. They don’t choose though and they’ll play Wii another day as far as I’m concerned.

  5. I’ve booked Grand Cayman for Spring Break 2017 all points and mile + taxes. Stay 5 nights @ Ritz Carlton (280K Marriott from SPG) and fly on AA from MIA (AVIOS).

    • I booked spring break 2018 in Grand Cayman, too! Not going to be in this “should we or shouldn’t we” situation again…I hope! 😉

      • We did Grand Cayman Summer 2015 with all three of our boys (6, 4, & 2 at the time). We weren’t sure what to expect as it wasn’t the planned out vacations we are normally used to, but we LOVED it!

        We much rather preferred the Holiday Inn Resort, which is the quieter side of the island and the suites were FANTASTIC (with laundry machines in the rooms). Kids also eat free!

        We also stayed over on the Seven Mile Beach area and it wasn’t nearly as nice.

        Rent a car and casually enjoy the island during your visit. Our favorite part of the island was probably Rum Point and Starfish Point. Both excellent areas with calm waters and shade for kids!

        • Good to know…that is our penciled in spring break 2018 destination when the girls will be 8 and 2.5. Should be fun!

  6. You staying at the Grand Wailea? I was there last June for my honeymoon and loved it! Look up the Monkeypod restaurant -it’s in a shopping plaza about 5 minutes away and has amazing food and Mai tais! Have fun!

  7. Travel with little ones can be truly exhausting. Your little ones are not of the age of crucial spring break planning and off school days planning. At your oldest age child you can teach them more in a week with travel then school ever will. When they reach middle school, it is then crucial. Consider a couple days stop in say San Diego to visit the zoo and Sea World. Then a 5 ish hour flight on too Hawaii. When your girls are older and more involved it will then become a more crucial and even more challenging plan with school and their sports and activities. Enjoy while you can……………..we did! This is the easy years of planning!

    • I totally agree, but do respect the school calendar (mostly). She is missing two days in February to ski and did miss 2-3 days in the fall to visit family. However, since they give us a full week off in the spring, I personally feel more comfortable using that as our full week to travel. Is so tempting to go for the better deals on other weeks though for sure!

  8. Mommy has 3 favorite seashells. Mommys girl has 4 favorite seashells. How many favorites are there? 3+4=7 favorite seashells. Draw it in the sand. Now Daddy gets to pick a favorite out of that. 7-1 = how many favorite seahells from the girls. Now we add up all of Daddys favorites and and Daddys girl gets to choose a couple to subtract from. My son became an einstien very quickly with this game.

  9. I had a miracle occur with changing flights to Maui. I had a United saver deal, with stops in SFO and LAX to get there. Was going to be an 16 hour travel day (not counting the drive to the airport, security, rental car, yada yada…). Then, a few months after booking, they emailed me the dreaded schedule change, and added an extra 3 hours in LAX. 🙁

    But one call to United, and they changed my ticket to a *one* stop through DIA, *much* better depart/arrival times. This ticket was only available at a normal redemption rate, but they gave me *zero* grief about any points/cash difference. I was shocked, and sooooo happy!!

    It restored a lot of my faith in the system.

    • United has always been great to me in that respect. AA gave me more resistance than I expected. They did at least fix it to something workable, but they weren’t nearly as responsive as United in opening up better itineraries because of the schedule change.

      • One secret with AA is to wait until within 30 days of the flight. I find they magically open way more Saver level space within the window that people making an initial booking would have to pay the $75 fee. As long as you are only changing times and not dates with point travel on AA, flight changes are free. This little trick saved my family tons of layover time when we were headed to South America. If there are still seats available on your preferred flight itinerary they will likely be offered as savers the closer you get to the date.

        • I will keep looking, but with it being spring break week to Hawaii and us needing multiple F seats I have low expectations. Fingers crossed though…

  10. Learned the hard away, had 1 of my 2 kids melt down, vomit, get sick, weather, delays, etc, etc. After that I decided never to connect and max 4 hour flights. I still travel with kids extensively, but enjoy beaches in Florida, California and different beaches in Mexico. I just came back from Cabo where staff was great with my kids.

  11. We have taken my 3 yo to Hawaii 3 years in a row now and I’ve found that the time change isn’t too bad. She’s typically so tired and her schedule so messed up by the time we get there that she falls into routine pretty easily. Utilizing centurion lounges where we can helps us keep our sanity too and gives her a whole (kids) room to run wild in

  12. Kudos to you for going for it!! I remember full-well the travel anxieties of flying with young children. I can fly for free (flight attendant) but after a horrifying travel experience which resulted in a passenger throwing oreos at my crying children, I didn’t take my family anywhere for two years… True story!

    • I’ll share that for sure – though probably not until after the trip is complete. I can say that we have had very good luck with hiring nannies in other places like Punta Mita, Cancun, Miami, and more.

  13. Mexico gets my vote uniformly. The value is untouchable. Share your views on Hawaii… The “cost/return”, especially with the little ones is simply not worth the emotional and physical drain. For us Texans, hard to match the convenience of the Mexican destinations. Oh my, I sound like the Mexican Ministry of Tourism… LOL!
    And, thank you for sharing. I am invariably smiling when reading your blog.

    • I love Mexico…for sure. Great value, close to Texas, great people, etc. Will return there again soon I hope! Hawaii is simply in a different category for us. I don’t know if it will truly be worth the effort and time to get there, but I hope it will. I can say with certainty that I have no plans to book another Hawaii trip after this one until the youngest is well passed the tough toddler phase.

  14. I think you made the right choice! Maui is my favorite place in the whole world. Both the Hyatt and Andaz there are great but the kids will really like the Hyatt in Kaanapali. It’s really set up well for kids, my daughter was only 8 mo when we were there last May but she had fun! The pool there does fill up quick so if you want a good spot for the day I recommend putting your towels down in the morning and then coming back when you are ready 🙂 Enjoy!

    • Agree, as adults we loved the Andaz and I’m glad we will be returning there, but most of the trip is at the Hyatt Regency and it seems perfect for young families!

  15. At least you were able to re-work the flights to make it less painful. I’m sure you’ll have fun either way. However, since you’re staying at the Andaz Maui, I highly suggest buying a non-slippage mat for the bathroom. You have a suite, so I would assume there is a tub. We stayed in one of the regular rooms with our 3 year old (at the time) a year and a half ago and I found the room not kid friendly – sharp edges everywhere and the shower (only option) is very slippery, my kid almost fell. The pool is great though – but not the service.

    • I find someone local each time. Often I go through the hotel’s kids club and sometimes can hire one of their staff when they are off-duty. Or I do internet research for well regarded local agencies and contact them.

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