Best of Both Worlds podcast: Consider a 5-year travel plan

2020 was something of a bust for travel, for obvious reasons. But life is slowly returning to normal. So maybe it’s time to start dreaming and planning again!

In this episode of Best of Both Worlds, Sarah and I suggest coming up with a 5-year travel plan. No, you don’t need to make hotel reservations for 2026. As we’ve all seen, travel plans need to be held loosely, as life can change fast. But it’s still fun to ponder the future. So sit down with your family and think about what you’d like to see and experience in the next few years. Where would everyone like to go? What would they like to do? When, roughly, could those things happen?

By thinking through a 5-year travel “portfolio,” you can think through the next years more holistically. Going camping in a national park and a big trip to Europe aren’t pitted against each other. In five years, you might be able to do both — and when everyone knows their favorite things can happen, there might be less conflict over any given trip. Plus, you can plan in terms of timing and finances…and start looking forward to trips.

Sarah and I talk through where we’d like to go with our families. My kids advocated for Paris, Japan, Norway, and Hawaii. Where would you like to go? This could be a great topic of conversation for dinner. So why not start talking? Let us know how it goes! And in the meantime, we always appreciate a rating or review wherever you listen to podcasts.

17 thoughts on “Best of Both Worlds podcast: Consider a 5-year travel plan

  1. What a great episode, so much fun to start thinking about possible big trips. Hawaii’s definitely on my list and Legoland in Denmark.

  2. This was SO inpiring, thank you! I came home and announced to my husband that we’re doing a trip over the Winter Break this year 😉 It was a good reminder that we have only a limited number of years esp with the older kids, so these things DO need to get planned in. It’s so easy to have yet another “quiet break at home” and let all these opportunities pass by (esp with kids in 2 schools, the times where their breaks align is minimal).

  3. This would be a fun exercise for those who aren’t able/willing to travel much (as is the case with us – we don’t travel much when our kids are super young – basically one trip/year that requires a flight and then weekends at my parents lake home). In 5 years, our kids will be almost 6 and almost 9 – so a completely different stage of life!

    We moved when our son was about 18 months. If they can have an overlap between their rental and new purchase, that is ideal. We closed on our new house and moved in a month later. We gradually moved things over and that made it more manageable for us. We did a lot of purging before the move. We needed to declutter before listing so we ended up renting a Uhaul for 2 hours on a Saturday morning and moved a bunch of things over (we sold at an off-peak time (november) so our realtor was very particular about how we staged our house – but it sold in 2 days so paid off). We packed ourselves as I couldn’t justify the cost of hiring someone to do that, and then we hired movers to move everything. They said we were the most organized family they’d moved, possibly ever. We moved on a Friday while our son was at daycare – we dropped him off as early as possible and picked up him on the later side that day and were actually 100% unpacked by the time we went to get him around 5! Moving some stuff ahead of time (like a lot of non-essential kitchen stuff) really helped! We only moved about a mile away and we had all the boxes on the main level when the movers came so they could quickly load the truck. And we were good about labeling where the boxes would go as so the movers could bring the boxes to those rooms. All that said, I am super type A so probably an outlier in how I handle moves. But I aim to be 100% unpacked asap because seeing boxes of stuff sitting around drives me crazy.

  4. Not sure if SHU will see this, but no DISNEY trips on there?? Living so close and with 3 young kids?? And their big 2020 Disney trip was cancelled, I think. Or maybe I missed it somehow. That just surprised me to not hear disney mentioned! Or maybe that’s just like a quick weekend trip for them from South Florida? 🙂

  5. Great episode!! We love to travel and I’ve kept a version of this for many years on a Google Doc. I keep track of all the places we want to go – and since we only have one kid, which trips might be a good fit at what age. If there is something that would only work in a particular time of year (e.g., biking through tulip fields in the Netherlands for April break, not February), I have a little * next to it. The format has stayed the same for a long time, but the order of the trips changes as the years go on and we get excited about one location or another. Our son is now 8 and this has worked well for us.

    I have a row for each year and then the following columns:
    – Age of our son
    – Foreign language studied at school that year/ relevant school themes (for example, our school system has a focus on Ancient Greece and Rome in 7th grade)
    – Feb Vacation Break
    – April Vacation Break
    – Summer Vacation
    – Thanksgiving Vacation
    – December Break
    – Weekend Trips Jan-March
    – Weekend Trips Apr-June
    – Weekend Trips July – Aug
    – Weekend Trips Sep – Dec

  6. Oh I love this TB. Just the one as well so I always think we are super flexible but good to plan ahead. We are in the UK so mainland Europe feels quite accessible, but I feel like we should do some forward planning. My parents moved to Portugal so we will likely go there 2x a year for some sunshine. But Legoland probably makes sense for age 6 or so? And I really want to do a Netherlands cycling holiday with my husband. And there are tons of places in the UK we haven’t been.

    We have Christmas break, February half term, Easter, maybe another half term in there (kiddo isn’t at school yet so I’m not as au fait with kids schedules), and summer break. We tend to tack things onto my work travel which is nice, but isn’t super intentional.

    1. Hi CB! We are from Europe as well and all our family and many of my clients are located there as well (though we live in the US). I was the same as you – before our son entered elementary school I took him with me on all my international business trips from Japan to Russia and all across Europe. My husband or our family would join and watch him while I was in meetings and then we’d make the most of the time there together! We actually traveled to Denmark a couple of years ago and had a wonderful time – it’s a great family destination. We did go to Legoland for an afternoon, though all of us preferred the adjacent Lego House (especially the restaurant where you build your food selection out of lego pieces and are then served by lego robots!!). If you have some time, I can really recommend their open air museums on all things Vikings and Ice Age in Roskilde, Lejre & Ribe, fossil hunting in Mon, Odense, the Family Sea Explorer Wadden Sea experience, the Moesgaard Museum (!), and of course Copenhagen (our son loved the sidewalk trampolines and the super-interactive aquarium the most). Hope you can make it!!

  7. We have started planning trips for 2022: Portugal over Christmas and new year for grandparents, York for a conference (with husband and kiddo tagging along for the train museum!), Portugal for a conference and grandparents, English seaside with some cousins, and then hoping for a couples long weekend somewhere in there. But I’m gone 3 nights a week to begin with so I suspect there might be an element of wanting to sleep in my own bed?

  8. Love this! We’ve started developing a loosely-held multi-year family plan. It feels so good to dream again, and even better to make plans. Life isn’t a dress rehearsal; we might as well live it fully.

    We are going travel crazy in 2022 (VRBOs booked for all):
    – Lisbon and Barcelona for Spring Break (9 days)
    – London, Edinburg, and Dublin for summer (2 weeks)
    – Vienna and Budapest for Christmas/New Year’s (8 days).

    I’m also planning some weekends:
    – Romantic fall weekend in Montreal with my husband
    – NYC weekend with my little guy
    – Dartmouth weekend with my big guy
    – NYC weekend with my mom and sister for her 40th birthday blowout.

    2023 — more loosely held — will be 2 weeks in Greece and Italy during the spring or summer, and possibly a Copenhagen-St. Petersburg-Stockholm trip, plus some smaller domestic jaunts.

    Time to start dreaming about 2024!

  9. I don’t want to be a spoilsport but there is no mention in the podcast or the comments of climate change or the need to curb long distance leisure flights. Is this something you just don’t think about at all, or do think about but decide the problem is too big for your own personal efforts to make any real difference so do it anyway? Just asking really because it’s something I am really torn about.

    1. Thanks for raising this. It’s so important. I think a good approach is looking at how many flights might be involved and how to reduce them. So getting trains where possible and perhaps prioritising flights for things you’d find hard to give up. There is a trip mentioned above where a family could easily get a train from London to Edinburgh and ferry to Dublin. It’s worth finding out about these options.

      1. As the person who left that comment: that’s precisely how we’re moving between London, Edinburg and Dublin – for environmental reasons, which are hugely important to me.

        For Vienna and Budapest, we’re taking the train between.

        And for all these trips, we’re seeing as many cities as possible in the allotted time to minimize trips across the ocean.

        Plus I’m buying carbon offsets for all these flights – not perfect, but it helps.

    2. I think about this a lot! Ultimately I’ve decided to make changes in my life to reduce my personal emissions when it’s not going to make my life significantly worse – so I still travel (but take a train or bus when it’s a reasonable option) because it’s important to me, but I also avoid consuming animal products as much as I can, use renewable electricity, live in a small home, minimize my driving commute, generally avoid buying/wasting too much stuff, and do a bunch of smaller things like composting or using recycled toilet paper. I do this all because it is a part of my values to care about my personal impact, but I need to also prioritize my happiness and my relationships with loved ones which I do through travel.

      And in the meantime I work towards things that will have a greater impact on emissions, like efforts to elect politicians who will make real change including locally, contacting my elected representatives, and donating to organizations that are helping. I also want to figure out a carbon offset program to support when I travel, but I haven’t yet figured out which one.

      I don’t know if this helps, but I guess what I’m saying is that it’s important to consider the impact of your actions but there are many ways to do that, and ultimately we are going to need to transition to cleaner technologies rather than expecting a hugely different lifestyle from everyone for things like travel.

  10. Such a great and fun thing to work through. This did make me think about races. Race-cations for run races or triathlons was a thing that my husband and I did even before we had kids and is something we should cast forward a bit to see how it fits with family vacation too. Going to go track down some of the big city ones and see what their entry (lotteries) are like and plan that out.

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