The 5-year travel plan revisited

About 18 months ago, Sarah and I did a Best of Both Worlds episode on our 5-year travel plans. We’re going to be revisiting that topic in our Patreon discussion next week (noon, eastern, on Thursday June 22 if you’d like to join the community before then!)

I’ve been thinking about this a lot as I remember that my kids are getting older. My eldest will likely leave for college in approximately 2.25 years. While it’s entirely possible that he will spend some time at home during school, and potentially go on trips with us then, it won’t be automatic (and I never came home for more than a week or two after going to college — I got jobs elsewhere in the summers).

Even before college, kids have their own things they like to do. We considered a President’s Day weekend trip this past year, but didn’t go because one child was in a competition. And we have a situation this summer where we’re taking an extended family trip (booked a year ago) and so a different child elected not to go to a competition he’d qualified for (he was totally fine with it —  but I’d like to have it be open time if he qualifies next year. We just didn’t know when it was when we booked — or now that I’m thinking about it, even that he would do that activity…).

So I am plotting out possibilities. Each year there are a few potential slots that work with the school calendar. We wouldn’t travel for all of them (it would be extremely expensive and exhausting) but we could for some.

School is out from mid-June to the beginning of September, and my husband can usually take two weeks or so during this time. I can take kids on more trips (individually or collectively) but we probably would only be able to do two with him.

There is Thanksgiving…we often haven’t done anything this week because I hear horror stories of Thanksgiving travel. But the kids get a half day on Wednesday that could probably be skipped, giving us a 5-day option if we wanted it.

There is Christmas. I like to be here for Christmas itself (so Santa can find us! And I sing in Christmas Eve services) but we would then have Dec 26-Jan 1 or so.

We have some days off around MLK weekend and Presidents Day. We tend not to go anywhere during the first because it comes so soon after Christmas (two weeks, generally) but that is a possibility for a shorter trip. The kids get two days off for Presidents Day so we’ve definitely done that in the past but now we have the competition issue (it’s an annual one).

Spring break happens some time in March/April. Since it corresponds with Easter (usually) I tend to want to sing in Holy Week services, and thus get back on Thursday or Friday. But I wouldn’t have to (and I might not this coming year — I’m trying to do a bigger trip with at least the older boys).

And those are basically the slots. So, I have been trying to plot out how each year might work, and how to create each year’s “portfolio” of travel. None of this is set in stone, of course. Life can intervene (my travel portfolio for 2020 didn’t exactly happen…). And possibilities can come up — such as this extended family trip. But still, I think it’s an interesting thing to think about, and creating longer term travel intentions means more people’s interests can be accommodated. You can balance the expenses each year (with big trips vs. little trips) and have things to look forward to.

How far ahead do you think about travel? And do you have any trips you want to be sure to take while your kids still live at home?

Photo: Resort bands from a trip taken many years ago

16 thoughts on “The 5-year travel plan revisited

  1. We did do several big trips without various kids due to various extra-curricular commitments – and one year I put my 16-year-old on a Greyhound from Moab to Denver so he could do half of our family vacation and still participate in state finals for debate. I also felt fine about them missing school for travel.

    The kids are all grown now, and I turn 50 in a few months, so my travel calculus has shifted. I’ve started asking, if we only have 20 good travel years left, where do we want to go? I hope to have more, but I also don’t want to act as though time is infinite. This question has definitely changed my thinking!

    In the next 18 months, I am planning to go to Antarctica for two weeks with my husband, ride my bike from San Diego to St. Augustine with an all-female tour group, take my mother to Prague, and ride the Natchez Trace with my dad and sister (I’ve done that by bike before, but it will be different to do it with them!)

    1. @Seppie – I love this! Those sound like amazing trips. And yes, best to not assume an infinite amount of time when travel will feel doable. I definitely know some folks who put off travel to retirement and then found it a lot harder than it would have been in their fifties… Of course, since I had my youngest at 41 I will still have kids around in my 50s, and still be dealing with the school calendar!

  2. We are entering into the same general timeframe as you, just slightly behind, as my oldest will be a freshman in the fall. We seem to have LOTS of conflicts on the travel calendar which has me feeling a combo of sort of sad/ frustrated!! Traditionally we have usually counted on a good chunk of time in early August for travel- after my younger son’s summer swim season ends (end of July) and before all the back-to-school stuff starts (usually end of August here, but soccer often starts up mid-August). But my oldest is going to a new school for high school which operates on a bit of a different calendar, so he will start up again by August 15th now! Then he will get out earlier in May, but… my younger son will still get out later, in June.

    And then high school sports seem to start maybe even earlier in August, further reducing that window of opportunity. I also have generally always been turned off by Thanksgiving or Christmas travel, just given the crowds and increased prices!! Yuck. Our big windows have usually been early August and then an extended trip over spring break (our spring breaks usually don’t line up with Easter, although it looks like next year it does… hoping this isn’t a new thing?).

    This past year spring break was mid-March for us, and we pulled the boys for a 2nd week to do a 2 week trip. It worked out perfectly as it was just BEFORE the peak travel weeks and crowds over Easter! We are usually more likely to do 2x 2 longer trips per year, for a variety of reasons (saving on airfare, for one, and also just to have more time to really explore a place and/or visit family, if that’s relevant on a trip), versus scattering tons of short trips all throughout the year.

    But going forward with the HS schedules, I’m not sure how it will all shake out. I’m pretty sure our typical “pull the kids out for a week before spring break” will maybe not fly so well in high school. In terms of how far in advance we plan, I usually start sorting things for about a year in advance or so. I’m currently eyeing options for next spring break and/or an early June trip next year. The June trip seems to have potential to be… a more complex destination! It’s already testing my trip planning abilities. Hahaha!

    1. @Kae – yep, school calendars + sports limits the window, and while we could pull kids out for a day for the older kids it really starts to matter. Both of my older sons had slightly disastrous tests after being absent for a few days due to school trips (like not even our family vacation – stuff they were doing for school clubs/classes). So…we really need to be careful on planning.

  3. My son is nearly 6 so we are thinking about when we’d like to go places when. We spend 2 weeks at Christmas and 2 weeks in summer in Portugal with the grandparents. We want to go to Copenhagen next Easter (with a trip to Bilund for Legoland) and are hoping to do a summer home exchange in Amsterdam.

    He gets 10 days in October and 8 in February but my teaching breaks don’t coincide so he typically goes to local camps these weeks rather than travel, but my dad thinks he might come and pick him up in February and he can go hang out with them.

    1. @Coree- those sound like nice long breaks during the year but yep, if they don’t correspond with parent work schedules than it really doesn’t do much to help! We don’t have long breaks during the year (1 week for spring break, and usually 8-9 days or so over Christmas) but summer goes from now (June 16) to Labor Day (we will start on Sept 5). So we’re always going to be looking at a lot of summer travel I imagine.

  4. I think there are as many travel options, as there are personalities/families. Everybody just does whatever works better for them, and our preferences surely changed as the toddler ages are beyond us.
    I personally don’t like to stay home during the school break, because i don’t like to think about cooking and cleaning, even though we have local “adventures” like going to museums. So it simply doesn’t work for us. So we always take a trip right after Christmas Dec 26th till Jan 2nd up north to Wisconsin/Minnesota/North Dakota (we live in Midwest). It of course has some challenges of planning around the winter storms, but we usually are super flexible and can leave a day or two earlier/later and stay in a hotel before our cabin is ready if we see that the storm is coming. Our two boys take skiing lessons or just do some tubing then.

    We also take another week-long car trip in summer, where we rent a cabin/lodge and cook our own meals. Again, since we are in Midwest, it takes about a day to get out to see something exciting and new. We take one plane trip in spring, when we go to Cancun (because of non-stop flights from our city).

    Other than that, I my husband and i travel for work when needed (i usually go to couple of conferences each year), but we don’t do any short weekend trips. I feel it is too much work with packing/unpacking, thinking of the meals, and then we fall out of our rhythm for doing groceries/Sunday food prep. We just learned that with our personalities, the short trips are way more stress than fun, so we don’t. We also have one kid with very specific allergies, he cannot eat most of the fast food, so it is just easier for me to attend to his needs when we are at home.

    1. @Irene – I hear you on the weekend trips. We have taken several of them but boy is it a lot of work for not a lot of time! I guess 2 night trips are slightly better than one night trips – those are the worst in terms of the amount of packing and prep necessary but you don’t get much time at the destination…

  5. It’s an interesting idea thinking 5 years ahead for travel. I’d like to go to Japan at some point with the kids. I always find the years where I have planned and booked long weekend trips well in advance mean we actually go. I haven’t really gotten back into the swing of that since COVID and the amount of travel we have done in the last 12mo has been a lot less. I need to do start doing this again.

    1. @Kate – let this be a nudge to start thinking about it! It’s almost impossible to totally commit to stuff 5 years out. But when it’s a goal, then you can start thinking about it and getting excited (and saving for it if needed).

  6. Thank you for this! My son is 7 and not too much into scheduled activities yet, so I hadn’t thought about need to plan around him… We don’t travel much in the summer because it is beautiful in New England and there’s lots of activities to do and my husband has a big vegetable garden he takes care of. The last two years I’ve pulled him out of school for travel to come to conferences with me and to go to Florida to warm up in January during my break (and gotten not-so-subtle form letters implying I don’t care about his education… yet they were watching the Little Mermaid… I think going to DC museums and monuments during my conference is just as educational as the Little Mermaid.)

    In January, I’m on sabbatical, so we are going to Mexico for 3 months. I will have to plan home schooling, and I’m sure the district won’t be crazy about that, but I feel like, we only have one life, and slow travel lets you get to know an area and people instead of being a tourist, and that to me is more important than following the rules, expectations, and routines set by someone else. And I am perfectly capable of teaching second grade for 3 months. My sister is getting married in Italy in May, so I’ll have to take him out then, too, and if we’re going all the way over there, I want to show him the sites, like the ruins – he is really into Percy Jackson right now and learning about Greek and Roman gods.

    In 2025, I’d like to go to Harry Potter world. We are on the fourth book now, and I’d like to go see it with him while he’s still into it. At the end of this August, I’m hoping to go to Legoland in New York with him, too, possibly just the two of us. I feel like the window of time when he will like these things will close one day.

    I think one thing I’ve been struggling with since turning 40 is making all of the sensible choices and following rules and expectations at the expense of failing to put adventure and joy at the center of our lives. I’ve worked a lot, and delayed gratification, and been frugal to build security, all the things they tell you to do. We’ve done some great camping adventures and local things, but there’s such a big world out there that I want to see and show him, and I don’t feel like squeezing it into weekends and prescribed breaks. School and work are only a part of life. They’re not the center. And I have to remind myself that money is meant for enjoyment, not just security. It’s ok to spend on adventure.

    1. @LK – I think homeschooling can be a great idea if you’d like to travel for longer periods of time. You’d need to make sure you had your district’s curriculum goals and standards for the time you’re missing but for a 7-year-old it’s more feasible than, say, trying to teach calculus to a high schooler. This sounds like a lot of fun travel!

    2. LK – My kids are 9 and almost 7 and I have had similar struggles on doing the “right thing” and also living out our intentions. Travel is something I have decided to prioritize over many other things in life and yet sometimes it is still hard to pull the trigger! About 15 years ago, when my husband and I had been dating a year or two, his extended family did a short Disney cruise togther. I was invited, but the “expense” (though pricey, I could have afforded it) and the logistics (I had limited vacation and the travel timing was tricky) were both dauting and I said no and I have always regretted it. They’ve never done anything like that since and I don’t forsee anything similar in the future. I have a few destinations on my bucket list (taking my kids to Germany where I lived on an Army base as a kid) but a lot of my opportunities pop up and I want to be financially and mentally ready to say yes! I’m going to Ireland in August with my two sisters (just the 3 of us!) because one sister was going, the other decided to tag along and well, I had to join too! I turn 40 this year and my children are finally old enough to be good travelers so I too am trying to be proactive about making these adventures happen!

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