The Upside of (Travel) Planning

Spring European Travel Plan

I love it when a plan comes together.

It is the most alluring advice that never seems to work for us. We’re a bit skeptical it works for anyone in any real sense. But we recently discovered an entirely new way in which the seemingly world-wise travel advice to eschew planning in favor of “just going with the flow” fails us.

We admit we have a problem. We’re habitually goal oriented people. In fact, I think we can safely boil down everything we’ve accomplished in life to three simple steps:

1) Set a goal
2) Make a plan for achieving that goal
3) Execute the plan

Naturally, nothing is ever quite that simple in practice. It is nonetheless the rough outline of how we managed to leave successful professional careers at the age of 38 to travel fulltime. It’s how Shannon built a mobile freelance business from the ground up that has earned her the privilege of writing front-page feature interviews with former presidents. None of that could have happened by chance.

So if we’re hooked on planning it is because it works. And yet we’ve recently discovered an entirely different benefit that we either didn’t fully appreciate before or had mostly forgotten about: making a plan is powerfully motivating.

Thus far on our travels we’ve mostly been executing a plan set in motion four years earlier: traveling the U.S. from coast to coast by R.V. with occasional international excursions to escape North American winters. But now, with our domestic travels coming to an end, we’re in need of an entirely new plan. Where do we go? How do we get there? What do we do with all our stuff?

It’s a time of change and opportunity that should fill us with excitement. But instead of enthusiasm, we were feeling surprisingly indifferent. With our last big excursions to Hawaii and Alaska behind us, much of our remaining U.S. travel seemed utilitarian and uninspiring. Looking ahead we saw mostly chores.

Shannons Arrive Cover Story

Shannon’s cover story on President Bill Clinton

That’s not to say we had no ideas about what we’d do next. For a long while we’ve harbored vague notions of selling our R.V. and backpacking through Europe. But that trip never felt real. It was just an idea about something we might do far off in the future.

It wasn’t until we started researching and planning this next chapter of our life that the old excitement returned.

If ever we were going to leave the U.S. we had some decisions to make. For a trip as long the one we are planning, we’d need to work around Schengen area visa restrictions that restrict us to a total of 90 days throughout most of Europe before requiring us to leave for another 90 days. With careful planning we can work around that by moving back and forth between member and non-member states. But where to begin?

If we start in southern Europe – Portugal, Spain, Italy, Greece, etc. – we can set out earlier next year without needing to fill our bags with bulky winter clothing. We can then make our way north and leave the Schengen visa area in time for summer in the U.K. and Ireland.

Working through these decisions breathed life into our future. By hanging names and locations on previously gauzy visions of generic excursions we imbued them with a substance they never had before. Now, instead of a vague dream about some distant trip, we have a time and a place. March 2014. Madrid.

Suddenly it feels real.

Hey Europe, see ya soon!

Hey Europe, see ya soon!

And all those chores that previously filled us with dread seem less onerous. Now that we have a clear goal we also have a clear understanding of what we’re working toward. Each item we knock off our to-do list just moves us closer to that prize. It almost makes us eager to get to work.

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47 Comments on “The Upside of (Travel) Planning”

  1. Touring NH November 11, 2013 at 8:38 am #

    I find planning keeps me on the right course and less apt to get sidetracked. I find it rewarding to be able to cross off something on my list that brings me closer to my goal. Looking forward to reading all about your newest adventure!!


  2. Anne Helmers November 11, 2013 at 9:21 am #

    My husband was very goal oriented…I was not. It was a good balance that helped us learn to plan some things and allow for spontaneity on our recent RTW trip. He had all our plane tickets in and out of countries pre-purchased so there was a framework but it allowed us to be flexible on our day to day adventures while there.

    I’ve got to suggest New Zealand for the RV experience!!! YOU WILL LOVE IT!!!!


    • Brian November 11, 2013 at 10:02 am #

      There’s definitely a balance to be struck between structure and flexibility. I doubt we’ll reserve anything more than a couple of days before we plan to arrive (except possibly over the summer where things might get booked up). That way we can stay places as long or as short as we want and head off in a different direction if we choose. But we’ll probably have a pretty detailed itinerary drafted before we leave. And although we’ll have the flexibility to deviate from that itinerary, my guess is that we probably won’t. If history is any guide, we’ll discover that our original plan pretty accurately mapped out the best way to do the things we wanted to do.

      And NZ has been high on our to-do list for a very long time.


  3. SoleJourner November 11, 2013 at 9:24 am #

    While I too would love to be one of those people that can just show up and ‘go with the flow’, I am a NYer who likes to set goals then knock ’em down, and I enjoy doing the research, and the sense of excitement and possibility that come with travel planning. Plus, goal setting has worked well for me thus far: 1.5 years ago I set a goal to save up and hit the road in January 2014 for at least a year of continuous travel. On January 7th I fly off to Belize!

    Your Euro trip looks great so far! If looking for a day trip when in Andalucia, maybe check out Frigiliana.


    • Brian November 11, 2013 at 9:53 am #

      Good for you. We loved Belize and we’ll definitely look into Frigiliana . . . thanks for the recommendation!


  4. Animalcouriers November 11, 2013 at 9:33 am #

    You’re getting closer and closer!


  5. Liam November 11, 2013 at 9:38 am #

    Great piece! I look at just the same way. Sure, drafting up a spreadsheet with train timetables, currency rates, and a detailed itinerary can feel mildly anal… but the act of researching not only makes the trip smoother, it makes it so rich as well. You’re able to make informed decisions, and can go into the trip with the right attitude – a sense of humour. When you have a sense how things work in a given country, you’re perhaps less likely to get nasty surprises – or at least you can anticipate the kinds of surprises you might have to deal with.

    As I often say, planning the hell out of a journey really does mean planning the hell out of a journey 🙂


    • Brian November 11, 2013 at 9:50 am #

      I like that last quote! We also totally agree that advanced planning allows you to make more informed and better decisions.


  6. digger666 November 11, 2013 at 9:50 am #

    As an expat who’s made London his home for better than half my life, and as a dedicated follower of your adventures, it’s exciting to learn you’re finally turning your attention to the Old World.

    With regards to Schengen/non-Schengen states, Eire has instituted passport checks for flights arriving from the UK, a procedure which didn’t exist in the 80s. Normally you may expect to receive three months leave to enter. If you arrive in the Irish Republic from some country other than the UK, your leave to enter Eire is applicable in the UK, ie: any remaining time on your entry leave may be spent in the UK.

    Normally, US passport holders arriving in the UK from countries other than Eire would expect to receive six month leave to enter, which does not appear transferrable to the Republic, although I shouldn’t, perhaps, extrapolate that from my recent experience.

    The above advice is based on my last arrival in Dublin, which, admittedly, was two years ago.

    Have a great time; I look forward to your further adventures.


    • Brian November 11, 2013 at 10:19 am #

      Hi Digger. Thanks for the info. I expect we’ll be sweating these kinds of visa related details as a fact of every-day life pretty soon so the more information we get the better.

      The relatively generous 6 months visa we’ll get from the U.K. & Ireland should be enough for our purposes. We’ll probably plan three months or so there and then either re-enter Schengen or maybe jet off to southern Africa for safari.


  7. mytimetotravel November 11, 2013 at 10:46 am #

    I always figure I get to enjoy a trip three times: once when I plan it, once when I actually travel, and once when I go through the photos.

    I’m looking forward to reading about your European travels, especially how you handle being an expat – I’m seriously considering moving back to England after nearly 40 years in the US.

    I noticed you mentioned leaving your travel flexible. Are you renting a car? An RV? if you’re using trains you’ll get much cheaper fares booking ahead – see for all you need to know about train travel in Europe.


    • Brian November 11, 2013 at 11:04 am #

      We’re still pretty early in our planning stages but I think we’ll probably use a mix of transportation options. Because we’ll only be traveling for a couple of hours between points of interest, we’ll probably just take the bus most of the time. We might want to rent a car in areas where public transportation doesn’t get us where we want to go (we’re thinking of doing that to get around Brittany and the Loire Valley in France.)


      • mytimetotravel November 11, 2013 at 11:17 am #

        Don’t discount the trains. I prefer them to buses as you can get up and walk around, and they have toilets. Don’t confuse the European system with Amtrak – much more comprehensive and often much faster (for schedules see: ). BTW, as RV people, do you know about this site?


        • Brian November 11, 2013 at 1:02 pm #

          I wouldn’t say we’re discounting trains. They’re an option we’ll probably use from time to time. We just don’t think we’ll end up spending more for the extra comforts of a train when we’re only talking about a several hour trip. And we expect most of our trips to fall in the “several hour” category. Besides, this is how we mostly got around Central America and it was fine –

          We thought about RVing through Europe but decided it’s not how we want to go. We expect we’ll spend a lot of time in European cities and RVing just isn’t an ideal way to do that. We also want the flexibility to jet off to Asia or Southern Africa or South America for a season, or longer, without having to worry about storing or disposing of an RV. We wouldn’t rule out getting another RV at some point (we don’t really rule out anything) but right now we’re thinking about backpacks instead.


          • mytimetotravel November 11, 2013 at 2:21 pm #

            Hmmm. Madrid to Seville, this week, bus: 22 euros and 6 hours or so, train: as low as 26.60 euros and only 2 3/4 hours. In Central (and South) America buses are the way to go, in Europe not so much.

            Your map is just a first pass, right? I’d hate to think that all you were going to see of Switzerland was the western edge.


            • Brian November 11, 2013 at 2:50 pm #

              We’ll be making our planes, trains, automobiles and / or bus decisions on a case-by-case basis. If we find out that trains are faster, more convenient and not much more money I expect we’ll be using trains. But may I ask, how far in advance do I have to book that Madrid to Seville ticket to get that price?

              And you are correct, the map is a first pass. But you might notice that more of Europe is excluded from our immediate plans than is included. . . all of Portugal, Germany, Italy, Hungary, Russia, Poland, Latvia, etc, etc. And of the countries we do hit, we’ll still only see part of them.

              But that’s O.K. We don’t intend to try to visit every country on the continent in three months. That’s not our travel style. We’ll take our time making slow and methodical progress through each country. The places we don’t get to on this pass, we’ll hit next time (a careful observer may notice a route starting in Southern Portugal traveling up around Northern Spain into Southwestern France left unexplored by this trip – that sounds like another 90 day spring-time-in-Schegen kind of excursion. Another 90 days may include Italy, Switzerland and Germany – heading north or south depending on time of year. I expect we’ll piece together several of these 90-day itineraries before all is said and done.)

              Meanwhile, it took us four solid years to work through the U.S. It will take us at least as long to do Europe justice. We’re in no hurry.


            • mytimetotravel November 11, 2013 at 5:00 pm #

              Those were the prices for Wednesday this week. Only one train at that price, but it was the middle of the day, not early morning, more options available next week. Yes, lots and lots of Europe to explore – and some interesting places are still outside Schengen (think east). Glad you’re planning to make it to Portugal, don’t short change the center and north.


            • Brian November 11, 2013 at 5:39 pm #

              Thanks for the info. We’re OK with off-peak travel to save a buck. Good to know that the trains aren’t quite as expensive as I’ve heard.

              We’ll definitely be spending time in non-schengen areas . . . about 180 days a year, at least. 😉


  8. Anne-Marie November 11, 2013 at 11:32 am #

    You guys are definitely goal and action oriented. Great to read.
    It is tricky with all these restrictions that are put on travel and staying in one specific country.
    I am originally from Sweden so I am also a Swedish citizen (and an American) and the only country I can stay indefinitely in, besides the US, is Sweden. Even as a EU citizen I can only stay the 3 months in another EU country.
    The UK allows people to stay 6 months and I also found out that Georgia (which is pretty far away from your travel plans maybe) allows for a 360 days!
    If you go as far as Scandinavia, you will find Sweden and Stockholm to be extremely pretty and beautiful in the summertime. Stockholm is gorgeous with all the water and greenery.


    • Brian November 11, 2013 at 1:06 pm #

      Didn’t know that Swedish citizens had visa restrictions through Europe. Kind of a bummer.

      We’ve spent a week in Stockholm and some of the surrounding countryside and definitely need to get back to spend some more time there. Georgia might take us some time to get to, though. Maybe we’ll hit it when we pass through Turkey. Who knows? It’s a big world with lots to do.


  9. Ben November 11, 2013 at 11:44 am #

    Plans . . . that taboo word that some will rally behind and others against. When it comes to visa technicalities like Schengen countries have, then certainly know ahead of time. But itineraries? I’m still hanging off the fence about those.

    Good luck with your Europe trip though.


    • Brian November 11, 2013 at 2:02 pm #

      Here’s what I like about itineraries: If you look at the map at the top of this blog post, I know I can do all of that in the 90 days I’ll have available. I wont be stuck somewhere needing to do a boarder run. I won’t find I’ve run out of time before I get to do the things I really wanted to do. And yet, if I find something I want to do differently, there’s no reason I can’t still do that. But at least then I’ll know what my trade-offs are (e.g. “if I make this detour I’ll have to cut these other things out. Is doing this new thing worth giving up these other things I originally planned to do?”)

      But here’s the thing, having planned ahead I’ll have a good idea of what all those options are before heading out. What we usually find in practice is that there’s a reason something didn’t make it on our itinerary in the first place. And that’s because what we planned to do suits us better.


  10. Erin Elaine November 11, 2013 at 2:54 pm #

    I agree, I usually like planning. If you don’t plan, sometimes things are sold out (Alhambra) or you miss a fun festival that you didn’t know was happening. Once a hostel I’d reserved had accidentally overbooked the 10-bed dorm I’d requested, so they upgraded me to a private room for the duration of my stay! That would never happen with people who just show up and ask for a room. By doing my planning ahead of time, I save time while traveling and can spend my time having fun rather than going from hostel to hostel to find a bed or showing up in a city on a day when all the museums are closed.


    • Erin Elaine November 11, 2013 at 2:55 pm #

      Forgot to add: Yay Madrid!!! I love living here and I’m sure you’ll enjoy your visit here.


      • Brian November 11, 2013 at 5:40 pm #

        Yay, indeed. How’s the weather in March?


        • Erin Elaine November 12, 2013 at 4:14 pm #

          It can still be a bit cold in the mornings but nothing unbearable. I’m from Seattle and I was fine with a light jacket and a scarf on some days.


          • Brian November 13, 2013 at 5:28 pm #

            Thanks. That’s kind of what we’re expecting / hoping for.


    • Brian November 11, 2013 at 3:09 pm #

      We obviously agree. Getting shut out of something you want to do blows. And so does spending valuable daylight hours wandering around looking for lodging. Far better, in our view, to plan ahead during downtime so that we can spend more time doing the things we are actually going to do.


  11. mcmeeshi November 11, 2013 at 4:50 pm #

    We are going through a parallel experience! We’re at about 19 months with Peace Corps, living in Jamaica, getting closer to fulfilling our 27 month assignment. We’ve been itching to travel again and have had a lot of vague ideas about what to do next. But only recently have our goals and plans started to come together and solidify. It completely changed our outlook and makes the last few months here a little lighter! We’re looking forward to a roadtrip through the Canadian West and spending next Fall working in France, with lots of stops in between!


    • Brian November 11, 2013 at 5:41 pm #

      Sounds pretty cool. The Peace Corp is something that has been on and off our radar for a while. The long-ish term commitment has kept us from pulling the trigger though.


  12. Deb November 11, 2013 at 9:27 pm #

    We’ve backpacked through Europe a few times. You’ll enjoy it for sure. You just might have to be a bit more “go with the flow” in Italy, Spain and Greece, especially if you are using public transport.


    • Brian November 11, 2013 at 9:39 pm #

      We get that and that isn’t a problem.


  13. Sam November 12, 2013 at 10:21 am #

    Very smart! Having to work around the Schengen visa issue must be tricky – I’ve been lucky enough never to have to consider that, being a European citizen myself. But it looks like you’ve found a good workaround!


    • Brian November 12, 2013 at 10:27 am #

      We envy your European travel freedom. Although if we were European, we’d have had similar visa restrictions traveling around the 50 U.S. states these past 4 years. With Schengen Europe is just doing to us what we’ve done to you all for forever. 😦


      • Sam November 12, 2013 at 12:12 pm #

        To be honest, for me the main benefit of being an EU citizen is the ability to live and work in any other EU country – I value that more than the travel freedom. I for one really hope the UK never leaves the EU! But yes, you’re right, I guess you can’t have it both ways…unless you had dual citizenship. That could be handy!


  14. Allison November 12, 2013 at 1:24 pm #

    Where will you sleep? What will you eat? Seriously, are you planning to use Vacation Rental By Owner type places, or hotels? What about food? One of the things Jim and I struggled with in Germany was the food. We’re not fans of the wurst and ended up at many a grocery store salad bar. Will you be able to do self catering? If you did want to RV, there are places in the UK that “sell” you and RV and then “buy” it back when you’re done. We thought about it, but decided the pain of learning the European system of parks, and pumping our own propane was just more than we wanted to take on. I do envy you the trip and am looking forward to your posting from the continent.


    • Brian November 12, 2013 at 3:40 pm #

      All good questions, and ones to which we have no specific answers. On previous trips we’ve used a combination of hotels, hostels and VRBO type accommodations. We’ll probably do the same this time around. With respect to procuring food, we prefer to self cater when possible. Otherwise we look for inexpensive street food.


  15. horeramtanti November 15, 2013 at 9:34 am #

    Great article.


  16. Bronwyn Joy @ Journeys Of The Fabulist November 17, 2013 at 10:56 am #

    I love planning.. but I hate following plans. One of the fastest ways to kill off a goal of mine is to plan for it – by the time I’ve planned something I’m bored with it already. The things I achieve are more likely to come about through spontaneous, terrier-like following of a trail.

    But I don’t begrudge people their plans. There is a time for either method, of course, but I’ve noticed you can’t take a planner and tell them to go with the flow and expect everyone to be happy. Likewise, I die a little when people insist I do everything as was laid out!


    • Brian November 18, 2013 at 3:11 pm #

      Of course there is nothing requiring anyone to follow a plan once it’s made. In fact, “planning” is just another word for thinking ahead. It doesn’t bind you to anything. And yet we always get that same push-back every time we suggest that people give a little thought to what they want to do and how they want to do it. It just seems obvious to us that approaching things in a thoughtful way is always, and in every instance, superior to doing things thoughtlessly.

      In fact, your terrier metaphor works as a proof of concept. It’s rare that you see a terrier accomplish anything of note by itself. Mostly you just see them being lead around on a leash by someone else who knows where they’re going. 😉


      • Bronwyn Joy @ Journeys Of The Fabulist November 18, 2013 at 8:46 pm #

        The thing about the terrier is that when they accomplish something off-leash it’s because of prior training 😉 . I like the idea of learning coupled with flexibility.


        • Brian November 18, 2013 at 10:13 pm #

          Of course planning doesn’t reduce ones flexibility in any way. Not planning, meanwhile, often limits ones options.


  17. Betsy November 17, 2013 at 7:30 pm #

    Thought of you guys when I read this article – – maybe it’ll come in handy when you do actually get to Europe. 🙂


    • Brian November 18, 2013 at 3:20 pm #

      Ha! We’ll keep that in mind. Thanks.


  18. CurlyTraveller December 23, 2013 at 9:36 pm #

    I couldn’t agree more! I love to plan things, to a certain extent. And I find that that gives the best results and adds value to my travels.

    I admire people who achieve the same satisfaction and results by going-with-the-flow.
    In my opinion both is fine; whatever works for you.

    Too bad that often people look down on travellers who like to plan. In terms of ‘control freaks’. And in terms of ‘ I am so much more adventurous, daring and in-the-here-and-now’ then you are.



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