How We Enjoy Family Travel

June 22, 2023

This is 100% inspired by a great recent travel post from Cup of Jo: the #1 trick to enjoying family travel.

Expecting that everything will be easy + perfect = recipe for disappointment.

Some things will go wrong (extreme deep freeze in Montana; flat tire in Chicago; COVID on camp visiting day*) and some things will go right (kids enjoying ski school; delicious ice cream; cousins playing together happily).

*Okay that one actually DID kind of suck!

This is definitely a travel-heavy summer for us. In addition to Jo’s wise reminder, here are some of the things that help us (and me, personally) enjoy family travel . . .

1- Above all, remember travel is a privilege — so it makes sense to try to think/act accordingly! Just getting in a plane as a family is enormous privilege. There may be annoyances, but it’s best to remain good natured about it all. I feel like there are certain people who always seem to have a good time (example: Kae!) and others who tend to nitpick. It really is more fun when you generally take the little microdisasters in stride. If everyone is okay, then they will only add to the memories.

2- You usually get what you pay for. Someone recently commented noting that we could travel less expensively. 100% correct! And trust me – I am well aware 🙂 But I don’t always want to choose the most budget-friendly option. For better or for worse, I actually really enjoy accommodations on the ‘nicer’ side, and trying fancier restaurants on occasion. They are part of the experience for me, aaaaaaand yes — they cost more. The trade off is that maybe we will do fewer (and/or shorter) trips, or choose more adventures that are close by. And that perhaps our vacation ‘slice’ of the overall budget will be larger than in some other families. I am okay with that. I’m sure other slices are smaller (housing, home decor, and cars come to mind).

(I DO try to take advantage of things like credit card points or frequent flier when I can! They do help — every kid in our family has frequent flier numbers!).

((ALSO this is all relative. There is a ton of fancy travel that is just 100% COMPLETELY out of our price range!))

3- 1, mayyyyyybe 2, things per day. I know — this one may be controversial. But we are of the ‘quit while we’re ahead!’ mentality. We enjoy down time on vacation, and so do the kids. “Regular” life can feel hectic and exhausting, and I don’t want my vacations to feel that way! Usually one (and sometimes 2) anchor events is plenty for any given vacation day, and I love building in a day or two of very little in the way of obligation.

Things like Disney/skiing – we are never the first ones out there, NOR the last ones standing. And I prefer it that way!

4- Exercise can fit into vacation if you want it to. I know some people like to relax and take vacations as a break from working out. I felt that way when the kids were younger (maybe because at that time, it was physically exhausting to be away from home with young kids!). Now however I prefer to keep up some running/activity most days. ESPECIALLY since I often go to places with better running weather than we have here. My runs are often a trip highlight (they definitely were in San Diego + Evanston!).

5- Alcohol. I probably have something like 2 drinks per month under normal circumstances, but I do drink more on vacation — often a glass of wine most nights, especially if we are out to dinner somewhere fun. I am okay with that, though may experiment with less on our longer trip this summer just because too many nights in a row and I REALLY feel the difference in sleep quality.

6- SEE THE PEOPLE! If I’m going near where friends live, I am going to make plans (preferably in advance — people are busy!) to meet up with them. I always find it worthwhile and fun, even if it isn’t always logistically easy. I also am always so amazed how instantly natural it feels to be with old friends.

cold in June in Chicago!

I think travel is SOOOOO individual and I am in no way saying my preference are in any way ‘right’. It’s just interesting to reflect on! If you are a person who loves cramming in multiple activities each day and recoils at the thought of an early run on vacation – totally reasonable 🙂


  • Reply Coree June 22, 2023 at 5:41 am

    I love this! We’ve just got the 1 and travel in Europe is cheaper / shorter distances, but we do make an effort to get away quite a bit. It helps that my parents are in Portugal so we’ve got a default destination for Christmas and a few weeks over the summer.

    I like to be out exploring and the idea of an unstructured week or two at home makes me anxious. I assume I’d embark on some big project and annoy everyone/have them annoy me. We have much more generous annual leave so we could take off most breaks if we were strategic about it/split up.

    We do pretty mellow days whilst traveling though, 1-2 core things, lots of eating ice cream in cafes, etc. I don’t want to rush through things and get irritable because my 6 year old wants to dawdle.

    We’re doing our first Home Exchange this summer so hoping that goes well because it feels like an economical and socially responsible (when we consider airbnb impact on big cities) way to travel. We’re hoping to do some camps abroad as well – swim camp this summer and then maybe 3-4 weeks in Amsterdam, working remotely while kiddo goes to art camp. We live in a small town and it feels like a nice way of exposing T to the broader world.

    • Reply Sarah Hart-Unger June 22, 2023 at 7:32 am

      1-2 core things and ice cream – sounds a lot like us!! Europe seems like it would be amazing for easy travel though the US is so big and climate/landscape is so diverse that there’s a lot to see here too!

  • Reply Jen June 22, 2023 at 6:16 am

    Our day-to-day life is pretty chill so I like to have a busy vacation. This spring we took our first vacation that was booked by a travel agent and I LOVED being busy without being the organizer. My girls are a little older than yours (12 and 9) so it is easier to accommodate my “busy preference” than when they were younger.
    In fact, we did not go on many vacations before the youngest was 6 because the itineraries that worked for their limitations did not sound worth the money at all.

  • Reply Grateful Kae June 22, 2023 at 9:16 am

    Haha, well, I DO try to always have a good time!! It usually works, though of course there are always inevitably a few bumps. 🙂 I think not nitpicking has a lot to do with that. Also, I think part of it is also that I do a decent amount of prep before the trip. So I try to really limit unwelcome “surprises”, like showing up at a museum on a Monday to find out they are closed on Mondays! Or that I needed advance tickets and now it’s sold out, etc. I also try my best to get a feel for the vibe of a location or an area so I can best figure out what area I want to stay in, is it convenient to restaurants, do I need a rental car, etc. I also like to try to anticipate areas that I could get tripped up. For example, we are not big city/metro using people where we live. I had read stories of people getting utterly lost and confused using the NYC subway system, so before we went there, I watched some You Tube videos and sort of studied how it all worked. Then I had no issue when we got there!

    I also agree that you HAVE to know your family’s travel style and work within those boundaries! In our case, we don’t usually like to go places on vacation at the crack of dawn. Oftentimes travel advice will tell you you “have to ” be to the theme park, the national park, the trail, the museum, wherever right when it opens. I just usually disregard that! Ain’t happening for us. We enjoy slower mornings, hopefully with a cup of tea/coffee and somewhere with a view, before heading out for the day. I sometimes think we have better luck *not* following the masses, anyway, in terms of crowd control. I know to generally not schedule anything for us before about 9-9:30, ideally. (There are exceptions, of course.) We’d much rather shift the whole day later and maybe not have dinner until 8 p.m. and a slower evening, versus being up at crack of dawn and in bed before 9.

    We do a lot on our trips but like you, it usually does work out to just 1-2 main things per day, plus some downtime at a brewery for a beer or an ice cream stop, etc. So while we would rarely go back to the hotel to like, nap, I always am mindful about the rhythm/ pacing and allowing for some form of downtime. Oh, the other thing I always consider on a multi-destination or road trip is travel days! I know I don’t want to have back to back to back days of long days in a car and/or flights too close together if I can help it. So I usually try to stay at least 2 nights in one location if possible, and I pay attention of the timing of longer day trips vs. when we need to drive on to a new destination that will also involve a longer drive.

    Great post/topic!!

  • Reply Lisa of Lisa's Yarns June 22, 2023 at 10:13 am

    We have done limited travel with our kids because we don’t really want to spend a lot of money on travel at their ages (currently 2.5 and 5). Our vacations have all been very low key – trips to the Gulf Coast or trips to AZ to visit my sister. We ALWAYS stay in an airbnb. Even when I am not traveling with kids, I prefer airbnbs so I can prepare some meals at home. I get very very very sick of eating out and would prefer to make breakfast for myself. I stay in enough hotels for work that they do not feel special and OMG they are so expensive. My bill for 2 nights in Chicago in early June was $1000!!!

    We will also pay up for direct flights and optimal departure times. So we won’t take a 7am flight or return at like 8pm. I don’t even like to do that as an adult. Getting to the airport at 5am is so rough and especially with kids. Sure we could get there earlier or stay later and get more time at the destination, but if we take such an early flight, everyone is too exhausted to want to do much. I definitely recognize the privilege in being able to be particular about departure times, though.

    Lastly, we try to come back on a Saturday so we have Sunday to do laundry and prepare for the week. We are not looking to eek out every moment of vacation time that we can. I do not like getting home on a Sunday and going back to work on Monday.

  • Reply Emily June 22, 2023 at 4:18 pm

    I am a little the opposite of Kae in that we kind of prefer earlier mornings and then early bedtimes. Our kids are 9 and 10 so who knows, this could change as we get older. I also find that since we live in the eastern time zone and tend to vacation west of us, this often works out so that we are not adjusted to the new time zone (mountain or pacific, or once–Hawaii) and we get up even earlier than we do at home and like to get an early start on the day.

    We also like to do 1-2 core things and built in down time, as others were saying. I do love to have time to just read and relax on vacation, and the kids usually need some down time physically because we tend to have active vacations with lots of hiking/swimming/etc and they get tired!

    We are definitely getting travel budget “creep” lately, and part of me has freaked out about it a little but then I remember that our kids are now at GREAT ages for travel and we saved a LOT money on travel when they were young and we never flew anywhere, did lots of vacations to see family, etc. It is time to lean in for the next several years until they leave home! My husband and I have slightly different preferences in terms of “luxe” on vacation–I think I’d rather take more/longer vacations with more basic accommodations but he’s the opposite. However, we recently landed on what we think is a decent compromise–we all four love camping, but only for 1-2, maybe max 3, days. So we are thinking about exploring some destinations (the 5 southern Utah national parks, for instance) where we can do a mix of nicer accommodations (with separate bedroom for the kids) and camping. This will keep the overall costs down but also allow us to splurge on some slightly nicer accommodations part of the time.

    • Reply Debra June 24, 2023 at 9:27 am

      If you have a rising 4th grader, entrance to US National Parks is free for 4th graders and their families… I believe if in one car. Starts September and runs through August.

  • Reply Erin June 22, 2023 at 4:34 pm

    Love this! I definitely follow the motto of keeping expectations ROCK BOTTOM on family vacations. My kids are at really great ages for travel now, so I can expect a bit more out of them (7(he’s still iffy), 11 and 13) but still – like you said, 1-2 things during the day and build in some downtime! We also do MUCH MUCH better overall if the kids have their own room, and even (precious little snowflakes that they are) their own beds. Knowing that helps us to plan what we need. We take FULL advantage of credit card points/miles which helps us budget too.

    We just did a trip with my husband’s whole family – 10 adults, 10 kids ages 3-13 all in one big house and that was tough – I tried to manage my own expectations there and we DID have a good time, but I have no interest in repeating that experience anytime soon. We went to Utah and it was tough to not be able to do all the things I know I would want to if it were just us! However, the kids had a BLAST with their cousins, lots of pool time at the house we rented, and we saw beautiful scenery, which was what I hoped to accomplish. We’ll just have to go back on our own!

    • Reply Sarah Hart-Unger June 22, 2023 at 4:55 pm

      yes to the kids’ own room and beds. Otherwise we end up with some annoying combination of kids sleeping with parents . . . ahh well. 2 kids in one bed does not seem to work in any combo.

    • Reply Lisa of Lisa’s Yarns June 22, 2023 at 9:15 pm

      I have done a huge family gathering in one house with a similar number of people. It was sooo hard. We did it in January of 2020 for my parents 50th wedding anniversary – 12 adults and 9 grandkids! My oldest was just shy of 2 at the time and was an EARLY riser at that time, like 5 am. Trying to keep him quiet was so hard. I don’t want to experience that ever again – I’d much prefer separate accommodations for each family! It was in Minnesota in the dead of winter so we didn’t miss out on many activities but I was limited in what I could do since our life was still dominated by naps.

      We also splurge on accommodations with different rooms for the kids. I think/hope that our boys can share a room with separate beds by next year (they are 2.5 and 5 now and the toddler is still in a crib).

      • Reply Jordan June 22, 2023 at 10:37 pm

        My husband works for a startup and a few years ago they rented a big Airbnb for all the employees (all 5!) and their families to spend a long weekend. The place was huge so luckily we had our own space, but we had the only baby/toddler on the trip (newly 1 & 3) and it was so hard! I was constantly chasing my newly walking 1 yo around, and the 3 yo was getting into everything. It was so weird to be trying to make a good impression on his coworkers while juggling the kids and then with the time difference, the kids were up crying at 4:30am. They still do a family offsite every year, but now they get everyone their own hotel rooms and have kid-friendly activities, SO much better!

        • Reply Erin June 23, 2023 at 11:58 am

          Yes! My kids are great ages for this, but I felt for my SIL who has a 2 and 5 year old…. it was tough for her for sure. I have BEEN THERE and those trips were so rough. I am already working on my MIL that next time we do this it’s at an all inclusive resort 🙂

  • Reply Daria June 23, 2023 at 11:47 am

    A few observations of how we do it.
    1) Low, low expectations
    2) Remembering that more often than not, the trip is for US (or me, if I’m traveling alone with the kids). The kids (3 and 5) generally don’t give a shit where they are or why they are there. They are simply tagging along with us and learning life skills such as flexibility, adaptability, and cultural awareness.
    3) Pay more for “humane” flights – so worth it.
    4) Melatonin for kids and us- a must
    5) Always an airbnb – never had a bad experience (knock on wood)
    6) Pace: the slower, the better. Lots of parks, playgrounds and cafes. A museum here or there. Soak up the feeling of the country/place. I like to sit and enjoy.

    • Reply Sarah Hart-Unger June 23, 2023 at 12:15 pm

      I had one bad airbnb experience but several good ones (and the bad wasn’t THAAAAAAAT bad.) Love these! Though have never tried melatonin. I’m always worried it will cause an early wakeup!

  • Reply Arden June 24, 2023 at 9:28 pm

    I saw the Yale sweatshirt and thought – darn SHU was in my backyard but I guess not in New Haven.

    • Reply Sarah Hart-Unger June 25, 2023 at 7:40 am

      Nope – it was a cousin’s sweatshirt she put on, only about 10 sizes too big!

  • Reply Nicole C Vinson June 26, 2023 at 10:39 am

    How we enjoy family travel
    1. Travel with another family with kids of similar age or even slightly older 🙂 We did two condos in the same building for Steamboat and it was perfect. Space but also connection!
    2. Plan a special girls adventure. We have one on the books this summer to unite 4 girl cousins. My travel partner is my cousin and she is the cool fun aunt. She is bringing my sister in law’s daughter. SiL is enjoying a week with one less kiddo and is not sad about it! So we have the 4 of us that like to do the same things all together for 6 nights. We might be crazy but we did 3 different lodging locations for ultimate fun in Maine. We are glamping, whale watching, hitting up THE national park, and taking two nights at an Embassy Suites indoor kids pool) by the airport for ease of travel. We have two nights at each location. Tough to do with a different group but these adventure girls (almost 5 and almost 8) seem ready. I will report back on whether this is a disaster. Ice cream will happen 5/6 days if I was a betting woman. Not bringing siblings might also be the hack. When the boys are the same ages, they can have a trip for them with the dads/ fun uncles.
    3. Say yes. I say yes to the kids and yes to me. Yes to the souvenir. Yes to the screens. Yes to 20 more minutes in the pool. I say yes to the crazy outfits. Yes to the in room dining. Yes to the starbucks run. It is vacation..:)

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