How We Are Funding Our Next Big Trips

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Over the weekend I wrote about my current travel dreams and plans since I was gifted a few minutes to indulge in those thoughts as my baby slept in a little later than normal that morning.  Many of you took the time to share where you are with planning future trips, and I loved reading every single one of them!  It’s beyond great that most of us in this hobby can relate to simultaneously planning trips that are both on the near and far horizons.

When looking at the destinations on y’alls lists that aren’t just “pie in the sky” dreams, but are actual trips that are being planned, it is absolutely amazing to me how miles and points can help make so many amazing destinations a reality.  Along those lines, today I wanted to focus on not just which trips we are dreaming and planning for, but how we are working to make those trips a reality.

I mentioned a little bit of how I was funding the trips heavily using miles and points in this post, but I’ll go a little deeper into that here, and again I would love to read how you are focusing your mileage earning energy to make those trips a reality.

Miles and Points Used to Take My Family to Australia/New Zealand

This trip has been on my radar for roughly five years.  In fact, back when dinosaurs roamed the internet and the US Airways Grand Slam was still in action I was earning US Airways miles from that promo hoping to use them to fly business class on a Star Alliance partner to New Zealand.  I even started planning that trip a few years ago only to realize my heart wasn’t in it and I stopped since it was way too big of an investment to do when the timing didn’t feel right.

Well, life continued to be pretty busy the last couple years and this big trip kept getting put off “until next year”.  The US Airways Grand Slam never returned after 2011, and heck US Airways is no longer even an airline.  Of course my US Airways miles converted to American Airlines AAdvantage miles, but we weren’t able to find the availability we needed via OneWorld partners for the 3.5 of us to fly in a premium cabin (and while I’m no first class snob, Australia is too far for me to want to want to manage in coach).

Since US Airways miles were no longer usable for Star Alliance partners by the time we got around to actually putting this trip together earlier this year, we turned to United and MileagePlus miles.  Since United is our airline of choice thanks to our Houston location, and Chase Ultimate Reward points from cards like the Chase Sapphire Preferred® Card convert 1:1 to United, we were able to scrounge up the 450,000 miles it costs for the three of us to fly round trip in a mix of first and business class (though ultimately we should get some of those miles back since first class has been killed on that route).  I’ve been asked many times how we earned that many miles without doing anything crazy and the truth is that it took both of our accounts and a few years to get to that total.

Some of the total was earned from actual flying during the years I flew 75,000 – 100,000 United miles annually, some was from getting and using the United MileagePlus® Explorer Cards, and some was transferred in from Chase Ultimate Rewards.  Both of our United accounts have remained pretty meek since using that many miles.  In fact, Little C may currently have the largest MileagePlus account in the family since we have never used her miles!  This was a trip that we earned for and planned towards for years – it wasn’t a spur of the moment thing.  Ultimately we ended up using a different mileage currency than we initially planned, but since this hobby is in constant flux that didn’t come as too much of a surprise.  This trip is absolutely doable by most anyone in this hobby, but just don’t expect to earn enough miles to book Australia in business class for a family overnight.  This is a long term goal that may take a couple of years to attain.

Miles and Points Used to Take My Family to Europe

It is no big secret that the American Airlines AAdvantage award chart is likely going to undergo changes at some point now that the merger with US Airways is pretty much complete.  As such, using my AAdvantage miles is somewhat of a priority when possible, so I hoped to use them to fly at least the three of us to Europe in summer 2016 in business class (too early to tell if it will make sense to bring then Toddler S).  My AAdvantage balance is pretty healthy thanks to getting AAdvantage Citi sign-up bonuses through the years and the influx of US Airways miles via the merger.

I had booked our business class outbound flights into London on American Airlines operated flights for 50,000 miles each and was working on planning the return when this happened and all the sudden it made more sense to purchase the tickets, earn miles, and save our AAdvantage miles for another time.

So nice arriving "rested" in Europe

So nice arriving “rested” in Europe

The majority of our hotel nights in Europe are in suites and family rooms booked using Club Carlson points and taking advantage of the “last award night free” perk that came with the co-branded Club Carlson credit card until June of 2015.  We booked dates based on what we hoped would work out before that devaluation hit and as luck would have it we were ultimately able to book flights to align with those hotel reservations.  This is a good example of taking advantage of favorable award charts while they are around, even if ultimately you are guessing a little into the future in terms of what trips you may be able to take.

Miles and Points Used to Take My Family to Hawaii

This is a trip I am hoping to take with my family in the summer of 2017 but have not yet booked as it is still too far in the future to secure flights or hotel rooms.  Instead, I am still in the strategizing phase of this trip cycle.  I love Hawaii and have been multiple times, but this will likely be the first trip there as a family of four, and may well be the first trip we take when Baby S is over two years old and has to have her own seat (though she will likely start having her own seat well before then).

Hawaii is our perfect family destination!

Hawaii is our perfect family destination!

In recent history I have been able to use miles or confirmable upgrades to fly us to Hawaii at the front of the plane, but since my United status is dwindling (unless a miracle strikes) and first class award seats x 4 is pretty pricey, this flight may instead be at the back of the plane.  Eight hours is a pretty long flight, so we might break it up connecting on the west coast and letting the then two and seven year olds stretch their legs for a bit before heading out over the Pacific.

I will likely still have a healthy AAdvantage balance to work with, may book on United using Singapore Airlines award chart as I have in the past, or I may wait and pounce on a Hawaii fare war discounted ticket that seems to pop up from time to time.  I will likely have a few options for flights, but lodging may be a bigger challenge for my crew.

I will probably want to at least have a suite for us, if not skip the hotel route all together and opt for a house or condo. This will likely be our “big trip” for that summer since it makes sense to do fewer larger trips with a family than lots of short trips, and I don’t want us to all be cramped in a 300 square foot room for a week or so on our summer vacation with two young kids if we can help it.  So, I’ll continue to earn Hyatt points since I may use them to again stay at a nice suite at the Grand Hyatt Kauai, but I’m not ruling out trying out a house or similar for part of our trip.

Planning for lodging large enough for the four of us

Planning for lodging large enough for the four of us

Now that you have a little peek into how we earned/are earning towards our big trips I can’t wait to hear how you are making your travel dreams come true!!

Editorial Note: The opinions expressed here are mine and not provided, reviewed, by any bank, card issuer, or other company unless otherwise stated.

Disclaimer: The comments below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.

The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.


  1. It’s very interesting to hear your strategy for planning trips for a family where the amount of miles can double or more.

    We recently did a Hawaii trip (HNL and then to the big island) in economy. We had a long flight DEN-HNL but handled it fine, mainly because we were on a 777 so by booking 2 of the aisle/window pairs we had enough space to stretch out. We spent a day in Waikiki at the Regency and then flew over to Kona where we stayed at the Hilton. The kids loved the train and boats that are used to transport you through the resort there.

  2. Great post. Your family travel patters on points and miles are similar to ours.

    Take your toddler to Europe. We have had a toddler in Europe for the past 3 years and it has been great.

  3. Thank you so much for writing this up. I love hearing how real families are accumulating miles & points and planning trips — since I can’t relate to singles or couples 🙂 I’m dealing with a family of 4 (8 & 11 yr olds) and a pretty strict school schedule so it’s difficult to plan nice vacations without breaking the bank.

    For Maui (Summer 2016), I signed up for the Hyatt Chase and used my 2 free nights for the Hyatt Regency Maui and the other 5 nights will be at the Hyatt Residence condos next door (2 bedroom, 2 bath oceanview), and we paid for our flights since award availability was already gone by the time I was working on it.

    For NYC (Summer 2017), will fly with JetBlue and am working on accumulating more (hopefully their new partner has a better bonus option). Planning on using another 2 Hyatt free night certificates in the city and will either use Hyatts Points & Cash or free nights (now have the Chase Sapphire Preferred).

    For London/Paris (Summer 2018), would have loved to jumped on the BA’s business class flights and have 52,000 Avios for now. I’m slowly working on a game plan for accumulating AA points, and may possibly just use Airbnb for both cities as we definitely need room to stretch after a lot of sightseeing.

    New to figuring out when to apply for cards, which cards would work well for our family, and not just gathering useless points — it’s a little mind boggling, but I’ll figure it out.

    Thanks so much for all of your input!

  4. I loved reading your strategies! My kids are 9 & 7, so for 4 tickets very diligent strategizing is a must.

    Next year, we’re heading to Washington DC for 5 days over spring break. I transferred 36,000 UR points to BA and booked tickets on American. I used IHG points & miles for 2 nights at the Crowne Plaza The Hamilton. Then booked 3 nights in an AirBnb nearby.

    Then off to Europe in August. The plan is to use 100,000 AMEX MR points and Citi ThankYou points to transfer to Air France for 4 direct tickets to Paris. A mix of IHG points & miles and AirBnb reservations. Then train ride to London using the Barclaycard. Flight back to Chicago using 120,000 United miles, thanks to the MileagePlus card and Sapphire Preferred.

    I wish there were more hotel cards!

  5. I’ve been trying to use up the Aadvantage miles earned from the old US Airways card and our Citi card bonuses, but I am having the hardest time finding availability for 4 to any where we want to go for spring break. (That’s what I get for waiting until the last minute:). Instead I’m going to use them to take us to Tahiti to visit my mom’s family this summer. Since kids fly for free (well, just taxes) on Air Tahiti Nui year round, it’s not the best redemption value (only 1.2 cpm), but since we’re a little “points rich” at the moment, it beats paying $3,600 for the tickets. We’ll use the extra cash to get us to the Tuamotus on Air Tahiti instead.

  6. Just got back from Hawaii with a family of 5 (kids 9, 7, and 3), and I can highly recommend going the condo route. When we were on the Big Island, we rented a place with 2 bedrooms and 2 baths downstairs and a full kitchen and living room upstairs. It was awesome because our 3 year old was up pretty early some days and we were able to take him upstairs and let everyone else sleep.

    As for the flights, we flew coach both ways. On the way over, we had a brand new Airbus 321 complete with all the charging ports you’d need and video screens on every chair. On the way home, I swear we had the oldest 767-300 they have in service. No charging ports, only a video screen every couple rows, uncomfortable, beat up seats. Needless to say, the first flight was much better. You already know this, but others really will want to look at what aircraft they might be flying.

    The younger ones did really well both ways. The older one had trouble sleeping. I’m assuming this is because she is bigger and couldn’t get comfortable as easily as the other 2. Hawaii is awesome and we are already planning when we will be going back. Like you, I have a ton of AA miles I’ll want to burn and it is hard to beat some of the Off Peak prices for AA flights.

  7. Articles like this are not written enough. It’s usually aspirational this, aspirational that. Thank you for keeping it real. I dig nuts n bolts details.

  8. Great post.

    I’m glad that you laid out how long it took you to earn the miles involved. It took me a year to get the miles together for Asia and process is as important as the reward.

    For Hawaii, definitely recommend a condo. We had a two bedroom and it made the difference between calm and stressful. Also- if you can wait till the last week in August before school, you’ll save a bundle. I think your school starts before mine (DC goes after Labor Day) but prices go WAY down after August 15.

  9. Wow! Very inspirational and yes, thanks for the nuts & bolts! We have not done family travel much, and now are working on how to travel with a grandchild 🙂 after getting burned on credit cards, we have not used them! Will have to think about this….

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