Two Tickets and Four Flights to Paradise

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My daughter and I set out on an adventure to Kauai together. This all started thanks to a great deal last year on Icelandair miles that could be redeemed for first class on Alaska Airlines to Hawaii for a little over $300 for each round trip ticket.

The catch is you had to get to a city where Alaska flies in order to make the deal work. We decided to book direct flights from San Jose to Kauai and booked our positioning flights to San Jose separately. Usually I am very opposed to connecting flights when non-stops are available, but there is no way to get from Houston to Kauai without a connection somewhere, so breaking the trip up on the West Coast seemed like a pretty good idea to me.

Everything was booked and then a couple months before departure we got notice of a schedule change. There was no longer a direct flight from San Jose to Kauai on the day we were traveling, so we would now have to leave very early in the morning (6:30 AM) and fly to Seattle and then on to Kauai. I’m not an expert in geography, but even I know going to Seattle from San Jose means we were heading away from Hawaii, and lengthening the travel day by several hours. I couldn’t really adjust the days of my trip since positioning flights had already been booked with a different airline, so we were more or less stuck with this change. This crummy change.

When I checked into our United positioning flights to San Jose, I saw an option to “same day change” and take a later flight. We were already having to overnight in San Jose, but I could trade our early morning non-stop Houston to San Jose flight for a later departure, albeit one that had a connection. Since we had to have an early departure from San Jose the following day, I wanted to avoid two very early mornings in a row. If you are playing along at home, this means we were now up to four flights, alone, with a three year old, to get to paradise, A.K.A., Kauai.

I’d be a liar if I said I was happy with that plan. I was good with the original plan of one flight to the West Coast and then a flight on to Hawaii, but this seemed crazy. So crazy that I seriously considered scrapping and/or re-booking the whole thing a few days before the trip. However, that would have cost a huge amount and ultimately I decided we were tough enough to make it work. Or at least I sure hoped we were.

So, how did it all work out?  Here’s a play-by-play of what it is really like, the good, bad, and whiny.  😉

Monday 12:00PM

Excited and ready with toys for the first of four flights on our trip to Ha-why-aaaaaah as she proclaimed over and over with adorable excitement.


Monday 2:00PM

Cat nap on the first flight to LAX. Since we went sans car seat, the nap wasn’t too comfortable and didn’t last long.  The flight was easy-peasy though.


Monday 4:00PM (6 Central)

Getting re-hydrated and then  sleepy in the LAX United Club while waiting for our second flight of the day to San Jose.



Monday 7:30 PM (9:30 Central)

Eating dinner at the Hyatt Place San Jose. The food was edible, but the service was great. Very friendly staff helped keep our spirits up. Very noisy wall unit air conditioner helped keep us up half the night.

Monday 8:00 PM (10:00 Central)

I try to check in online for our 6:30AM Alaska Airlines flight and get an error message. I call Alaska and they say after the schedule change Icelandair never re-issued the tickets. Icelandair is closed until 12AM, so we can’t call them. Alaska says they can’t do anything even though they show us having tickets and seat assignments. This makes little sense to me, but I email Icelandair and go to bed knowing we have a problem waiting for us in the morning.. I hope for the best and prepare for the worst.

Tuesday 5:00AM

We arrive at the airport and just keep our fingers crossed everything works. The agent typed on her keyboard a little longer than normal, but I don’t mention a problem, and neither does she. We have boarding passes!

Tuesday 5:10AM

Fish tanks. Thank goodness for fish tanks.  It’s too early for all this.


Tuesday 5:30AM

Fresh fruit smoothie and oat bar for breakfast. Attempting to counteract the garbage food eaten yesterday.


Tuesday 6:05AM

Boarded our flight to Seattle and passed out almost instantly.


Really out.


Tuesday 6:45AM

No car seat again equals uncomfortable napping and again awake. I’m holding my breath she doesn’t completely lose it.

Tuesday 7:00AM

Mama, can I please watch Star Wars? Yes, yes, yes. Heck, I’d build you a light saber if you asked at this point. Please stay happy and don’t turn to the dark side. I know it is calling you!


Tuesday 9:00AM

After working laps around the N gates in Seattle to burn off some energy my kiddo decides it is time to make a break for it!  After being threatened with the loss of all Star Wars toys from now until forever we reunite and board our fourth, and final, flight to Lihue, Kauai.

Tuesday 10:30AM

The digi-players were passed out and the little exhausted one is still happy.  She has “read” the Alaska Airlines magazine cover to cover and picked out all the photos of Hawaii.  I think seeing the “end game” is helping her keep it together as well as she is!


Tuesday 12:30PM

Lunch is done, the toys have all been played with, and it is lights out for a solid hour and a half.


Tuesday 2:00PM

Ice cream on a plane, ice cream on a plane.  It doesn’t get any better.  All future flights without ice cream will be an utter disappointment.


Tuesday 4:00PM



Tuesday 5:00PM (2PM Hawaii time)

We land, get a rental car, fight with the nasty car seat, drive to the hotel, check-in, have 18 meltdowns, including a fit on the floor at the check-in counter, and the happy travel mojo has 100% worn off.  I’m still super proud of her for hanging in there this long.  The room isn’t quite ready, we are tired, and we both make grumpy faces.  Hers is 100% real.  Mine is 98% real.


Tuesday 5:01PM:

Oh wait, we can swim?!  Yippee!


Tuesday just before bed….

We made it.  We played, we swam, we saw huge waves, and then we rested.  As always, it is worth it.  Though next time we are taking a more direct route!


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  1. Amazing! I thought my kids were good with flying but your daughter is unbelievable! With your schedule, I think even my 15 year old would have had a melt down. LOL. Enjoy!

  2. I was wondering where paradise may be. Personally I prefer going to that other paradise in ~same time zone (Caribbean) until the kids get older. And it’s closer.

  3. Woah, what a trip. What a good job little C did! They can really bring their A game when they know you need them to.
    I’ll never forget what a trooper my (then) 5 yr old was when we were running late for our eurostar. I thought we should take the bus , not considering traffic, then we had a hard time finding the stop (we kept walking along the route, but not finding an actual stop) daddy thought the five of us should flag down a taxi (even though we hadn’t actually seen one all morning?! I may have used the F word – oops). When we were finally approaching gar du nord I explained that when we got off the bus we were going to have to run. So, she should stay right next to mommy and keep running. And she did it! And we made it!
    I can’t wait to hear about the fun stuff you guys did in Ha – why – aaaaah!

  4. Wow what a trip! 4 flights within 30 hours ! You are a brave mommy! 😉 and what a great trooper little C is! I don’t think I have ever done that with my three kids! That would drive me crazy even without the kids! Hope you stay long enough to make it worthwhile! Can’t wait to read your Kauai recommendations as we are going there in two and half weeks!

  5. Deals, she is and it was!
    Michelle, it would have been a well deserved meltdown. 😉
    ABC, Caribbean is great as well. We have a trip there early next year, but Hawaii was 100% worth all the travel and expense to get there…at least for us. She is already asking to go back!
    Jamie, they can be troopers for sure!
    Sharon, not sure I could have done it with three kids either, but thankfully it wasn’t that hard with my one. Will be writing about Kauai soon, but tons of great recs in the comments section of this post in the meantime.
    George, glad you liked the play-by-play. 😉

  6. Oh wow…after reading this, I’m even more surprised C still had the energy to run around in circles by the Hyatt check-in desk. I was a total zombie the first night we got into Kauai (and that was after a direct flight from LAX in the morning!). You guys enjoy floating around the pool complex there? The wife and I hung out by one of the waterfalls for a couple of days with a large raft. It’s awesome how they basically encourage you to have a float there. Not a lot of resorts are like that.

  7. Gabriel, I think it was our second day that she was running the real circles in the lobby. The first day she laid in the middle of the lobby while I checked in. Not much I could do about it at that point. Ha! She really runs on some sort of infinite battery though. She got home totally rested as well. Crazy! I loved this resort. My favorite was the saltwater sand pool. Tons of shallow spots she could safely plan in!

  8. “Ice cream on a plane, ice cream on a plane. It doesn’t get any better. All future flights without ice cream will be an utter disappointment.”

    Little C, Welcome to our world ! It starts out with ice cream. Next comes champaigne, lie-flat seats, premium scotch, etc … and eventually onboard showers.

  9. It was probably still your guys’ first day (we left Tuesday evening). So if she amped it up even more the next day, then wow! Perhaps she was just excited to go out to the pool? If I recall correctly (which could be wrong…we were rushing away from the property) I think you may have had a blue tube in hand? The saltwater pond was indeed fun! Nice and relaxing..easy to float in…no waves, yet able to hear the ones in the ocean. My only complaint about the lagoon was the large sand was VERY rough on the feet. But I suppose that makes sense since they don’t want fine sand making it’s way into the freshwater pool

  10. It is so delightful to read this piece! I had a terrible fight with hubby @MIA at the end of our 8-day Spring Break trip just because we were all so tired and short fused. Little C did a great job holding a good spirit for that long, I probably could not do any better than she did!

  11. Mommy points, great job on the post and kudos to you and Little C on being such good troopers! I am looking for the next post on this trip. We have a similar flight with 8 year old twin girls. We are staying in the Westin Villas in Princeville.

    AUS-SFO (UA) // SMF-OGG (AS) / OGG – LIH (HA)

  12. I also booked a trip to LIH out of SJC during the Saga Club ordeal. And I also noticed that when they rebooked us, there was some weirdness with the tickets. So I called Alaska to see what my options were, and they offered to rebook us on a direct flight out of Oakland even though there was no award availability, because it was Alaksa that had screwed us. Since I’m in LA, I asked, “Well, if you’re willing to let me switch to a departure from OAK, would you be willing to let me switch to a direct flight out of SAN?” After a minute chatting with a supervisor, she approved the switch and made a note of it in my record so that when Icelandair got in touch with Alaksa regarding the switch, my situation would be understood. It took 48h after I sent my email to Saga Club, but we were magically rebooked on a flight out of SAN. We leave in 8 days, so my fingers are crossed.

    Not to be disrespectful, but as weird as this whole Icelandair-Alaska partnership was from the start, you definitely should have been more prepared. In the future, make sure your PNR retrieves a record on And with Alaksa’s stellar customer service, it pays to be savvy.

    • Chris, it did pull up on checkmytrip with no issue. Not sure what else I could have done to be more prepared. Other than a schedule change that we were notified about from both Alaska and Icelandair, there was no hint of a problem until T-24. Couldn’t change the departure city at that point as we had already booked positioning flight to SJC. It was just one of those things….

  13. Oh dear. Why wouldn’t you just book a non stop 8 hour flight instead of spending 30 hours? That seems like a huge waste of a day.

    • Cogswell, no non-stop to Kauai from Houston, but we booked it via the Alaska air $300 F tickets. Was supposed to be two flights (and the return remained two flights), but through a series of events became four. Probably wouldn’t book it that way again, but it was quite the adventure. She is out of school right now, so we have days to spare. 😉
      Lisa, good luck! In this case I think daytime flights are a good thing. C wouldn’t have slept any better on a night flight, but that would have caused cranky meltdowns most likely!

  14. You are very brave! We are going to Kauai in July for 8 days with our 2.5 year old and 2 month old and we are not looking forward to our flights (IAD > LAX and LAX > LIH) but your adventure makes our travel plans look easy! We are flying during the day (leave IAD at 12:30PM, arrive LIH at 7PM) and stopping in CA for a few days on the way home to avoid taking a red-eye back to the east coast. Looking forward to your trip report!

  15. This makes me so thankful that I live in the SF Bay Area, going to paradise is an easy flight (even with a kid who gets sick on planes). But on the other hand, we haven’t make it out to the Carribean yet.. Still waiting for that day to come!

    A tip if you need to connect thru any airport in the Bay Area and your connection somehow requires an overnight near the airport, I would avoid Oakalnd airport as the surrounding area is a little scary 😉 and not many decent restaurants around (heck I am too scared to walk outside the hotel in that area). And if you connect thru San Jose airport, the Doubtree Hotel is a nice choice as it is within 5 min to the airport by their shuttle and it has a nice steakhouse at the lobby! 🙂

  16. “After being threatened with the loss of all Star Wars toys from now until forever we reunite and board our fourth, and final, flight to Lihue, Kauai.”
    You wouldn’t dare! LOL!
    Oh, and how would you get a lightsaber past the TSA? 😉

  17. Same thing happened to me. Got an email from Iceland Air. No mention of change, just flight info showing connecting thru SEA now. Looked on AS website and there isnt a direct flight from SJC on my departure dateanymore. Ok looks like AS created this problem. I checked OAK and there was direct flight to KOA. So I just called AS and asked if they could accomodate 4 of us in 1st class from OAK. After a few minutes, it was approved. For your case you could have done a 1 way car rental from SJC to OAK if AS could have re-accomodated you. more $, but its an option. more time in Hawaii….priceless

  18. Thanks! Excellent post. Damn she’s cute. Glad it all worked out in the end.

    Oh, and that decent steakhouse at the Doubletree near the San Jose airport? Its a GREAT steakhouse. Can’t be oversold.

  19. Always take the most direct routing with kids. I learned that lesson long ago…especially the overnight layovers are to be avoided…

  20. What a fun write-up! I’m really impressed with how humorous you were able to make it sound for what must have been a very trying time 🙂 The “ice cream” phrase is priceless. My 8 & 10 year old daughters haven’t yet flown first class, but I made the mistake of showing them a picture-filled blog review once, and now every time they ask if we’re flying in first… If they knew there was ice cream available, I’d never hear the end of it!

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