Travel Planning 2020

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In my little corner of the world there aren’t many better ways to spend a Sunday morning than at home with a blanket on the couch, drinking iced coffee, and working on travel plans while the kids are occupied with toys and cartoons. Such was my morning today, and with the catchy (and soul sucking) sounds of “Baby Shark do do do do do do” humming in the background, I worked on travel plans. With this summer already starting to wind down, I started with trying to firm up what we wanted to do next summer. I think that’s within the realm of normal planning parameters since next summer starts in less than 11 months and many airline schedules are already open into mid-June 2018. However, I didn’t stop there.

Adventure is waiting for us…


It is hard for me to know what works best for next summer without looking forward to seeing what else is waiting just over the horizon, especially since some of our trips are planned in conjunction with other family members. It helps me tremendously when selecting destinations and determining what types of miles and points to focus on earning when we can outline our bigger family trips not only for the near term, but for the next several few years. Sometimes those plans get scrapped and were never more than a line on a spreadsheet that gets erased, but sometimes the dominos fall in the right order, and what was once a line on a computer screen becomes a grand journey.

Where are we heading, mom?

As an example, I love Hawaii. I think it is my favorite all-around destination. We didn’t go to Hawaii this summer, so my initial reaction is to say we should be sure to go next summer. However, while it would be doable, my youngest really still won’t the perfect age for that flight next year. Not only that, but we have loose plans with multiple family members to go to Hawaii at the same time in 2019. Knowing what we hope to do in 2019 frees up 2018 for other destinations that will be easy peasey to get to with a then three year old, such as Banff and Costa Rica. The world is big, the options are almost endless, so visiting places in an order that aligns in somewhat of a logical way with ages and abilities appeals to us.

Planning to head back to Costa Rica with our kids next summer

If a really big, long, multi-island trip to Hawaii anchors the summer of 2019, as I hope that it does, what does that mean for 2020? Well, even though we are now solidly in crazy person territory in even penciling things in that far out, I think it means we take a big family trip to Europe. We will have a five and ten year old in the summer of 2020, and I think we could have a grand time together exploring Ireland, Scotland, Denmark, Norway, or who knows… Details aren’t important this far in advance, but having a rough idea of where we want to go not only helps me with the day to day, but it helps my mind have an order and purpose to travel related thoughts and activities.

Hawaii 2019

For example, I have 90,000 ANA miles that I need book for something in the nine months or so as they will expire. I could use them for something easy like the Houston – Calgary round trip we are strongly considering for early next summer. However, ANA wants 30,000 miles per round trip within North America, which really isn’t a great deal, though it is infinitely better than having the miles expire. However, because I have our future trips penciled in, I know that we are eyeing a no-kids trip to Europe in late 2018. This means that in a few months I can use 88,000 ANA miles for a round trip to Europe in business class on United or another Star Alliance partner, which is a really great deal.

I’m enjoying where we are at the moment with a just turned two year old and incoming second grader. Things like the beach, Disney, swimming, and more are a perfect fit for our phase of life and travel at the moment. However, it is also pretty exciting to think about what times like the summer of 2020 might look like with a five and ten year old. I am sure the girls will be much bigger the next time we are in Europe than they were last summer!

So much more of the world will begin to (re)open to us once we reach that phase of our family’s journey, so it is pretty cool to think about family trips both in this current phase, and the next.

I’d love to hear how other families pencil in trips and how many years out do you look and dream?

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  1. I completely understand the planning years ahead. My kid are now 8 and 11 and we have almost no restrictions regarding destinations. We entered this “stage” when the youngest turned 5. It’S a world of possibilities out there! We are now exploring the Balkans and they are old enough to understand the history of this place, appreciate different cultures, and remember what they’ve learned.

  2. Hi.

    You mentioned you not everyone in your family is ready for the Hawaii flight.

    In your experience what’s a good age to try that long of a flight? Our son is 6 months and we’ve had him on a few 2 hour flights but nothing longer. We’d probably fly out of Phoenix directly to Maui.


    • So I have a couple answers to this question. The first is that you can make anything work that you want to. I flew my 13 month old to Europe and it wasn’t always fun, but we made it. That said, we took her because we just really wanted to go and we couldn’t realistically leave her behind. From a practical standpoint, I think somewhere between 3.5 – 4 years old is when longer flights get pretty easy for most kids. You can absolutely do it before then though, especially a straight shot from Phoenix.

      • Please expand. Based on your experiences, how early are these trips “meaningful” to the kids? Beyond merely “doable”? Knowing what you do now, what would you differently?

        • I basically took my kids everywhere I wanted to go and they are now 22 and 20. They have told me they have no memories at all of any of our trips before about age 8 and really don’t remember much about anything before age 10-11. Doesn’t mean we didn’t have a great time but for example. we took them to see Chitty Chitty Bang Bang in London when they were 7 and 9 and they loved it but don’t even know what I’m talking about when I mention it. Go ahead and go where you want to go, do what you want to do, enjoy the experience. However if learning about culture, history, etc is your goal, I’d recommend waiting till after age 10.

          • I agree wholeheartedly! Your kids may not remember the hugs and kisses you gave them at an earlier age but that doesn’t mean that you shouldn’t show affection until they would remember it. I think travel enriches young ones lives even if they don’t remember it. As for Hawaii with little ones, we took our 1.5 year old and the flight was easy but the time zone change really threw her off and she woke up at 2AM (and wouldn’t go back to sleep) almost every morning. We still had fun but it was a little exhausting. At 4 she had no problems with the time zone change.

        • Also, having taken those 20+ year old kids many places (Egypt, Peru, Ecuador, Europe, South Africa, etc.) they both say their favorite trip was a week long rafting trip down the Colorado river through the Grand Canyon with some extended family. The only thing I could use points for was the flight but I’d agree that it is incredibly memorable and that’s what everyone who’s ever done it has also said when i’ve talked about it. (now my favorite trip was African safari but the rafting trip is up there for me too) The age minimum for this trip is 10 I think. Recommend you ask the booking company to be with a group that has other kids, it makes it even more fun for them.

    • I took my daughter to Maui from PDX when she was 8 mo old. She did great on the flight and it was actually really easy. That was a good age in Maui because for most dinners due to the time change she slept through the whole thing. Made for a lot of fun during the day and enjoyable evenings!

    • We took our 14 month old to Kauai this spring. A 9 hour nonstop to HNL and the quick hopper over to Kauai – both ways. It was a dream (granted, he has flown a lot since he was 6 weeks old). He had no issues adjusting to the time change and slept 7pm-6:30 a.m. He loved hiking with us and digging in the sand. I’d say go for it… But you know your child best. Hawaii is always a good idea in our opinion.

  3. Love this post! Also, thanks so much for putting “baby shark” back into my head after our kiddos were asleep already! 🙂
    For us, since we are in Europe, it is penciling in some of the cities we will visit with the kids as they get a little older. But, most of it with them now seems to happen more spontaneously. I have taken at least one kid with me on 4 trips in the last year that came up somewhat quick so we will keep rolling with that also. 🙂

  4. We currently have a one-year-old and are trying for baby #2 (crazy? maybe.), so right now I’m trying to decide if I can plan as far out as next spring and even then, just maybe a casual stay in Texas hill country accessible via car (we’re in Austin). I know we’ll eventually get back to more ambitious travel. I’m looking at this chapter as an opportunity to explore closer, domestic destinations that we had previously overlooked in favor of more exotic places.

    Thanks for the continued inspiration to get out there!

  5. I love this! My fiance and I are moving abroad next year and this is how I figured out our first year (2018-2019) budget…and a tentative one for 2019-2020!

    My friends get baffled by why I plan so far ahead, but doing this has so many advantages, like the ANA miles example! I figured out which countries and cities we’re going to visit next year so we know which miles to stockpile to get the airfare. I seriously applaud you for planning ahead for your whole family! It’s been quite an adventure just figuring stuff out for TWO adults.

    Truly nice to e-meet another efficient planner (obsessive planner, whatever!) 😉

  6. We are actually taking our kids next summer to Europe- 5 days Paris, 5 days Barcelona. They will be 5 and 9 years old so I think that will be doable and enjoyable for both.
    In the meantime we are hitting Aruba in November (you can never go wrong with all inclusive) and thanks to your post next spring break Grand Cayman (Westin for 8 days on points of course).
    Already planning fall 2018 (California road trip).

  7. It’s not just those with kids who make plans that far ahead. We have plans for 2020 but it’s for the Tokyo Olympics and I figure it will take that long to sort out flights and hotels.

    • This is on my radar, as well. I’m trying to position for a trip for 4 to Tokyo (for the Olympics) and another city in Asia for that summer–maybe Hong Kong? I also think it would be cool to hit Tokyo Disney while there.

    • From my experience with the Rio Olympics, it was the event tickets that I had to worry about most. For Rio, it wasn’t so bad since not too many people came, and the locals didn’t really turn out for many events. Tickets were fairly easy to come by in Rio, but I expect Tokyo to be very different.

      Hotels were another thing that was difficult because of how the Olympic committee snaps up everything that I could possibly use points for. However, I think AirBNB makes this easier.

      Award flights for me were actually sorted out 355 days ahead of time when the availability calendar opened up.

      I guess my advice would be – worry about tickets first of all, then hotels and flights about a year out.

  8. Seriously Stop – just Stop! Your kids keep making me get older everytime you post pictures of them. They are to cute and growing up too fast. 🙂

  9. Babies are different. We took our daughter to Asia (20 hours flying time) when she was 4 months old. Her mom took her again to Asia when she was 9 months old. She didn’t even cry for a single time. We went for a month trip in June when she was 19 months old (MKE-YYZ-MKE-YVR-MKE-HNL). She was just fine. In fact her mom was exhausted.

  10. Western Alberta is extremely beautiful, I highly recommend it. Both Banff and Jasper and the drive in between them are just stunning. I think the scenery in Alberta is even nicer than in Colorado. I do recommend going in June, just before school lets out in Canada, as in July and August it can be much more crowded. I also think the hotels are typically cheaper unless you are using points. The Fairmont Banff Springs is a must, one of my favorite North American hotels.

  11. That’s a lot of planning! Maybe you could aim for a Mars trip 2027, they’ll be 12 and 17, perfect age for inter-planetary travel. 😉

  12. I plan 2 to 3 years out as well. I pick a continent, and try to do 3-4 cities within that continent, with a few days in each city. Once that one year booking window starts to open up, then I finalize the exact city. A lot of times, it’s based on award availability at the time. For example, maybe there’s no availability for LAX – SYD, but maybe there’s availability for LAX – BNE. So I guess that means we get to explore Brisbane for a few days! Then we’ll just take a short hop to Sydney. Also, planning that far out also helps me set a goal for accumulating the necessary points and miles I will need. 4 seats in J is a no easy task. 🙂

  13. We’re the same way and have also started to talk about our (tentative) plans through about 2020. We’ve had to keep things very flexible with our youngest, who just isn’t as travel ready as her big brother was at the same time. We are THISCLOSE to scrapping a Labor Day trip this year because we don’t think she’ll be able to handle it. Maybe she’ll surprise us, but we’re looking into much closer Plan B options just in case. Even though I hate to wish time away (it goes so fast as it is), I’m looking forward to when she’s a little older and more comfortable with traveling (and going to sleep). Looking forward to reading about your adventures!

  14. As the kids grow older we focus our travel plans in “building memories”. We have done the Disney trips, etc but now we do 1 big trip a year to places that we know the kids will never forget. We plan summer trips of 2 full weeks and spend the miles, points and money to ensure every detail is perfect. We never travel on Spring breaks, longer weekend with holidays, etc.. We cab do many small and not that meaningful trips or one very meaningful big trip. Those trips have included all Hawaiian islands, London, Rome, Naples, Amalfi Coast, Sicily, Greek islands, and many more are in the plans. We think that mixing history, culture, beaches and amazing food experience delivers what we need for a memorable vacation that the kids can remember forever.

  15. The summer before my oldest son entered high school, it struck me that our beloved spring break trips were numbered. Once he left for college, his college spring break and my younger kids spring breaks would not align so I sat down and thought about the places I really wanted to go with the kids while we could still go as a family: an African safari, the Galapagos islands, Australia, and Costa Rica. I mapped out plans for what miles I would need to get 5 of us there and got to work. He is about to start his senior year of high school, and I’m happy to say three down, and one to go: our trip to the Galapagos is coming up in March!

    Travel has been such an amazing time for us to spend together. No friends, minimal time on devices (no overseas cell plans!), and just lots of great memories together.

    PS- Taking an African safari was amazing!

  16. The years are flying by too fast. It was only yesterday that I realised that we need to get positioned to be able to book a flight to Australia as soon as they open as we have a wedding to attend in Oz in August 2018. Already 2018 is fully committed and if my husband had more time off there would be more travel. However I have to say I think it pays to plan way ahead to be sure that what points are needed are ready to go in my preferred loyalty plan. Even though we are only booking for two, the points seem way harder to accumulate these days/

    • They do fly sometimes it seems and planning ahead really does help with the earning and maximizing parts of the equation.

  17. Im a planner.. We r cruisers before we r flyers,, we have been cruising since 2012 bec with a family of 4 that seems to be the most cost effective.. But since discovering this miles hobby this May.. we actually have 2 flying trips planned for this yr.l already… One to jamaica in sept courtesy of southwest points and another in thanksgiving back to orlando since we r already staying there for a week this august.. I have booked my cruises until feb 2020 since they r only opened until may of that yr.. And for nxt yr with my kids older now 9/13… Not much beaches for us.. But we have a lot of trips planned from before..A Southern Carribean cruise from san juan to aruba in Feb nxt yr, one of my bucket list, which again we booked two yrs ago and got an upgrade to a balcony which would have cost now $5600 but we only paid $3200.. It certainly help to plan in advance..we r also looking at hawaii nxt spring break using alaska air companion cert, however its still very pricey.. So plan b,, either cancun, puerto vallarta, los Cabos or punta Cana.. All inclusive this time. Depends since we will have two companion pass by then airfare will be cut in half.. Then summer of 2018 we r going to southeast asia and have been saving our bonus points from ink preferred and reserve.. To score at least 4 economy and upgrade with points or use the UR to score at least 2 premium economy and will try 2 business seats with a diff rewards system like citi thank u and membership rewards points with amex since i did an app o rama for hubby and im still planning to get CSP since im 4/24 and using those points for UR thru my CSR..
    As your kids get older the world seems to open up more.. And like u the farther i can plan things the better and i always get incredulous look from people saying how can i plan that far ahead.. But in doing so i have saved us a ton of money like the last cruise we had this yr to the western carribean.. We had a 2 bedroom suite for only $2600 with NCL and includes 7 day fine dining, drinks ( though we r not drinkers) free gratuities ( $200 worth ) and lastly $300 onboard credit to spend just because we booked so far and had gotten the best deals..
    So keep it up and i think for planners like us it makes us happy to know there are trips we have to look forward to everytime… Happy planning to all!!

  18. It gets easier, but it’s all in what the children are accustomed to that makes travel easier. Mine are 7 and 12. We are at the tail end of a 7 wonders of the world trip, left before Memorial Day and haven’t been home since. 35-40K miles butts in seats, mostly economy. Might try and squeeze in Hawaii at the end still, we love it too! 🙂

  19. I am having the opposite problem. Trying to figure out where to go for spring break next year and I’m struggling. (1st world problems I know.) We’ve done Hawaii, Mexico, Florida, and a few Carribbean islands. Some thoughts I’ve been floating are Aruba, Puerto Rico, Costa Rica, California-san Fran or pacific highway. Spring break is end of March next year and I usually prefer to go somewhere warm. I have kids who are 11 and 13. While I could be happy to lay on a beach all day, my family is more active…think scuba diving, water skiing, ATV’ing, etc. Anyone have any awesome suggestions for me? I have tons of UR points and primarily redeem through Southwest, United and Hyatt.

    • Costa Rica! Great redemption value and so many very active activities within arms reach of the Andaz Papagayo with the ability to still chill at the pool when you want.

      • costa rica is perfect for your family. Daily excursions for the active ones and great weather and relaxation (watching monkeys by the pool, so fun!) for the others.

        • It looks like the Hyatt there is not accepting points for booking for most of March Are there any other good options for lodging?

  20. Right now, we aren’t planning too far out (have an 18 month old and another on the way in January)… but we are always dreaming and researching places. We are currently in the process of booking a big trip for next spring – my husband has a month of paid paternity leave (taken anytime within the first 6 months of the baby’s birth – which is insane and incredible) and hoping to take a week of vacation on the front end to kick it off – our tentative plans are a week in Hawaii with extended family – continuing on to New Zealand/South Island – with potential stops to or from in Fiji and America Samoa to break up the flights (still working on the routing). We plan to spend close to 3 weeks in South Island in a campervan with both kids.

    We joke about how we plan crazy adventures when we are pregnant – our version of nesting ;)… Last pregnancy, we booked a RTW (Hong Kong, Phi Phi Islands/Thailand, Abu Dhabi) all in CX J and Ethiad Residence. It was an incredible whirlwind – and nice to enjoy time together for the first time in a year (we left our 10 month old with the grandparents for 8 days).

    The only other big trip that we are considering right now is Slovenia and Croatia for fall 2018 with both kids. Our oldest would so enjoy the Cow’s Ball and Festival in Bohinj, Slovenia.

  21. I’ve always planned our big trips about a year in advance, but now that I’ve gotten into points/miles I’m starting to plan out even farther so I have time to accumulate the points needed. My youngest is 4 so we’re also approaching the phase where we can go almost anywhere as a family. She’s still a little more difficult to take places than her sister was at that age (what is it with 2nd children?) but she’s getting there. This summer our big trip is Disney World.

    For summer 2018 we’re planning on Canada (Niagara Falls & Toronto). In 2019 I’d like to do a big California trip, but exactly what we do will depend on how long I can get off from work. I may also try to work in London for either 2018 or 2019, if I can figure out flights for the 4 of us. Beyond that I’m not sure. By summer 2020 my kids will be 7 and 11 so we’ll be ready for more extensive European travel, or something more active like a US National Parks trip.

    My kids also have a week off from school in February (the week of Presidents Day) so I like to plan a more local trip by train that week. We’re in NYC so we can get to several cities by train; this Feb we did Philadelphia, next year I think we’ll do Washington DC. The kids like taking the “big train” and these trips are pretty easy/inexpensive to plan, and also easy to cancel without losing money if weather or winter illness gets in our way.

  22. Our oldest is 9 going on 10, and will happily look at the map in a grand museum and find interesting things to see. Our youngest is just along for the ride. There’s a definite age below which kids really don’t get anything out of “big destinations”. We drug ours along because we literally had no choice. No grandparents or extended family to park them with for even a single night out. I call them “family trips” as opposed to vacations.

    We just got in the habit of sneaking in our own travel joys and well if the day was compromised by tantrums and changing diapers so be it. I’d really target long and costly trips for 3rd grade and up.

  23. We just planned out our next 5 years this week (before I read your post)!! Our kids are 11 and 13, so only 5 years left before the oldest heads to college 🙁 We are just focusing on the U.S., with a goal of seeing every state by the time our kids go to college. We camped for over two weeks out west in 2015 and did a little more than two weeks, 4 islands in Hawaii -mostly on points- in 2016. After supper the other night, we looked at a map of where we havsn’t yet been. I gave everyone post it notes to write down where they would like to go. Finally, we took each suggestion and placed it either as a fall break, spring break, or summer trip. We still had 4 open post-it notes after finishing 🙂 I like to plan ahead too so I know what I need to save, both monetarily and with points. Thanks for your blog!

  24. Love this post! I’m also planning ahead for a summer trip to Europe in 2019 for our family of 5. Since you’re thinking about it, I have a question if you have time: what are your thoughts on the best redemption US to anywhere in Europe? I’ve got CA to Hawaii down (Avios), but get lost when trying to decide what type of miles to stock up on for Europe. Its time for some new c. cards and don’t want to get the wrong ones! Thanks!!!

  25. I agree with many of the readers above in that there are different kinds of memory of travels as a child. While your children may not remember going to the top of the Eiffel Tower as a three year old, they will have the memory experience of learning to see new things and adjusting to other cultures because of early travel. Mommypoints has done a wonderful job of including our grandchildren in her adventures. What I am seeing in them as a result of exposure to so many wonderful places is an open friendliness to the world and an early ability to make friends easily. Because we have pictures and talk about where we have been, they are hopefully being infused with a awareness of many places and countries and the lifelong desire to explore.

  26. Summer – I look out a little over a year (when I can start booking hotels) but have a laundry list of places like you. Banff, which was supposed to happen this summer was replaced by GH Kauai when Cheap Avios flights on Alaska Air opened up SJC-LIH. And it was too convenient to use the Virgin America interisland flight rate of 3,000/ticket, So the 2 free CC nights to be used at Lake Louise were used at the Kea Lani – a nice trade-off.

    But without those CC nights, we’re looking at BW and others for Banff in June 2019 – of course we are so spoiled from Fairmont CC nights, we can only hope Accor will step up by then.

    Next June, we’re going to brave Manhattan with our project-runway-addicted 10-year-old ( I can only hope “Swatch” is still around Mood by then!). Looks like the best outsized point value for families can be found using Wyndham points, worth well over 2 cents for 2-bed rooms at their MSG-area hotels.

    On the agenda – Staten Island Ferry, Central Park, 30 Rock, a museum or 5, Subway ride at rush hour ( a must for any tourist!) Negotiating knock-offs on Canal St., Delis (Zabar’s & Katz’s RIP Stage & Carnegie), Dinner in Little Italy, Panhandling on an unoccupied corner, a few games of 3 card monte… ok, maybe not the last 2. Think I should watch The Out of Towners again…

    Is 10 too old for a leash?

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