Almost Fearless

The Biggest Mistakes to Avoid When Planning Long-Term Family Travel

Today’s guest post is by Sarah Lavender Smith from Away Together.  When she’s not being a kick-ass San Fran based writer, she’s traveling with her family.  I’m thrilled to share her tips on making it work.

parenting, travel with kids, guest post, hurdles

Above: The author and her family near Queenstown, New Zealand

A little more than a year ago, my husband and I were staring at a map on the One World airline site and feeling utterly bewildered. We had made the momentous decision to rent out our home for a year, travel the world and “roadschool” our two children — but where would we go, how would we get there and how long would we stay in any one spot?

And once we arrived who-knows-where, then what would we do and where would we sleep? We felt lost and overwhelmed — and we hadn’t even left home.

Now we find ourselves in a lakeside cabin near the quaint town of Daylesford, Australia, about an hour from Melbourne. Last week, we lived at an eco-lodge in the Blue Mountains National Park, and before that, we toured parts of the United States, Argentina and New Zealand. In the months to come, we’ll head to Hong Kong, Spain, Italy, and Greece.

In other words, we muddled through the highly subjective, somewhat arbitrary, always tortuous, often fascinating and just as often maddening process of planning a year-long family travel itinerary. Along the way, we learned from mistakes and developed a few guiding principles to minimize the time spent planning while maximizing the chances we’ll wind up in fabulous yet affordable places.

What follows are some of the biggest mistakes a family can make while planning a far-flung, long-term itinerary (and how to avoid them). Usually these mistakes stem from the kind of well-intentioned attitudes or assumptions expressed in the bolded statements below. These are statements I personally said or thought — before I knew better.

“Let’s see the whole world!”

The biggest mistake any family can make in planning an itinerary is trying to go to too many places and do too much. Keep in mind that packing, driving or flying, and then checking in and settling into somewhere new is stressful on the kids and kills the better part of a day. We’ve discovered our two kids (ages 8 and 11) and we are happiest when we go for depth over breadth; this is, we move around less and settle into a community for a couple of weeks.

During two months in New Zealand, we experienced both road-tripping — sleeping in a new town almost every night — and two-week stays at a couple of main destinations (Nelson and Queenstown). It was exciting to see so much, but overall we had a more satisfying time at the two-week spots, where we could get to know the community and establish normal family routines such as planning meals and doing schoolwork.

“If we’re going all the way to the Mediterranean, we’ve gotta see the Pyramids too.”

Related to the point above: Accept the fact you can’t see every “must-see.” While we were in Argentina, we agonized over whether to buy plane tickets and take a few days to see Iguazu Falls. Now we’re in Australia, and people are telling us we’re crazy to miss the Great Barrier Reef. I feel certain, however, that we’ve done the right thing by skipping both those destinations because of the time, money and effort it would take to get there. We’ve got enough “must-sees” on our calendar. Plus, some of the most interesting travel times happen outside of typical tourist destinations, in ordinary towns where real people really live.

“Won’t it be great to live in some of the greatest cities?”

Buenos Aires … Sydney … Barcelona … Rome — our itinerary began by connecting the dots between some of the world’s most alluring cities. We figured we would rent an apartment in them for three to four weeks and take just a few weekend trips to the outlying regions.

Then we wised up to the fact that we should limit our time in big cities, or at least balance it with time in the countryside. Cities have two main drawbacks: they’re expensive, and they can be stressful for children. The noise, crowds and security concerns grow tiresome, as does the inability to go out the front door and run around freely.

We had a fantastic apartment in Buenos Aires, for example, but our children really felt ready to leave after two weeks. Then we settled into a small town in the Patagonia Lake District, and they yearned to stay longer. Our kids are happiest — and by extension, so are we — when they’re in a more natural, less frenetic environment.

“I’m sure we can find someplace better if we keep looking.”

True, more research usually yields better results. But beware: travel planning can turn into a giant time suck. We could easily spend eight hours a day on the Internet reading about destinations, debating one over the other, comparing lodging options, and then trading emails with apartment managers and arranging overseas wire transfers to those who won’t take credit cards. We have spent days like that, and they’re no fun. Rather than searching for “the best” deal in “the best” place, we found it’s better to research just enough to feel that a choice seems pretty darn good, and then go for it.

“We can’t impose on people we barely know or haven’t seen in years.”

People we kinda-sorta-used-to know live in several places we’re visiting, but at first I hesitated to contact them. Then I got over my shyness and discovered how great it can be to meet up with others while traveling, especially if they have kids with whom our kids can play. In New Zealand, we met a friend-of-a-friend via Facebook and ended up having a magical day touring an area that only a local would know, and through this person we met a wonderful family who gave us the use of their house. In Italy, a couple we only met once is inviting us to their home and helping plan our itinerary around Venice. I look forward to returning the favor to a family from Sydney whom we met when they swing through our Northern California home next year.

So don’t be shy while traveling — tap into networks such as alumni groups and Facebook in order to meet people in your destinations, especially if those locals also have children. You can also follow other families’ travel blogs and try to meet if your itineraries cross paths.

“I can’t leave home without this guidebook — we need it now to plan, and we’ll definitely need it once we’re there.”

Before we left home, I bought at least a dozen guidebooks from DK, Lonely Planet and Rough Guide. And I loved them, I really did. I loved thumbing through their pages, highlighting their recommendations and marking them with sticky notes. They felt almost as essential to getting around as my passport.

But my husband made me leave them behind because we’re traveling as light as possible. He said we wouldn’t need them, and I admit it: He was right. Books are useful to get an overview of a region, but all the tools you need for travel planning are available online — including many books in PDF or other e-reader formats.

We cast a wide net on the web when we plan our itinerary and follow many travel blogs, but we return repeatedly to these sites: Trip Advisor, Lonely Planet and The NY Times Travel section. We also regularly use Google Earth and Google Maps to “see” a place in advance. (We’ve actually decided against certain apartments because the street view on Google reveals they’re in a place that looks particularly shabby or inconvenient.) And once you get to a destination, the local tourist info office is brimming with more free guides and maps than you could ever need.

“We can’t leave home until we figure this f***@#! itinerary out!”

I used to wake up in the middle of the night at home, survey the storage boxes and to-do lists scattered about, and think, How can we leave if we don’t even know where we’re going? How can I pull my kids out of their school and home if we don’t even know what city we’ll be sleeping in three months from now?

Now I realize it’s okay to fill in the details as you go. There is no way we could have planned everything before we left home — it would have taken too much time, and we were preoccupied with packing and moving out. All we did was determine the outline of the itinerary so we could purchase the One World tickets (and even then we changed dates and destinations along the way), and we found apartments in our first two major destinations. We also found a special place to stay during the Christmas holiday.

“Okay, let’s just go. We can wing it.”

Balancing the point above is the fact that we can’t just “wing it” because it takes work to find the kind of affordable apartment-style lodging or house rentals we seek. Families traveling for extended periods generally do better in suites, cabins or apartments big enough to sleep everyone together, plus a kitchen for cooking meals, which can be trickier to find than a standard hotel room. Otherwise, you’ll spend more money and have less family-together time when split between two hotel rooms and eating all meals out.

You’ll also need to plan ahead if you’re doing some form of homeschooling so that you have regular downtime in your itinerary for schoolwork, and so you and your kids can take advantage of the wealth of educational opportunities presented by the destinations. This doesn’t mean you should visit every museum and monument, but it does mean thinking ahead to where you’re going and how to approach it in a way that sparks the kids’ intellectual curiosity and enhances their academics.

Also, we learned the hard way to book far enough in advance for holiday seasons because some of the places we wanted to stay Down Under were already full during the mid-December through January holiday break. Similarly, if we were going to be in Europe over summer, we would have to book pretty far in advance. Generally, though, we’ve been ironing out the details and booking lodging approximately two to three months ahead of where we’ll be, which has worked out well.

“We’ll blow the opportunity of a lifetime if we don’t plan right.”

I start feeling flutters of anxiety about the gaps in our itinerary that we still need to fill for the last leg of our trip, but then I remember a title of a Jon Kabat-Zinn book, “Wherever You Go, There You Are.” The phrase helps me relax and have faith that we can make the best of wherever we end up if we have the right attitude.

It’s a mistake to think you have to plan perfectly to get the most out of your journey. Remember that choosing destinations and planning all the logistics will take you only so far on the road to happiness. Whether you have a positive experience traveling depends mainly on what you do as a family — how you interact with each other, and with other people and the surroundings — wherever you go.

About the Author:

Sarah Lavender Smith is a San Francisco Bay Area-based writer who blogs about her family’s travel at Away Together. Her post Halfway There Together: Surprises and Changes So Far reflects on how seeing the world and living a nomadic life has changed her and her family; she encourages other traveling families to check it out and comment on how long-term travel has changed them, too.

Pic: Luca & Vita., oaklandnative, geoftheref, telmos32, lecercle, ljubs

Christine Gilbert

I’ve been dragging my husband around the world since 2008 always with the promise that, “Yes, Drew there will definitely be hammocks there.”



  • Hi Christine & Sarah,
    As we are a family planning to take a year off to travel when our 2 girls are older (they’re 3 and 3-weeks old), this is great advice for us. Your article speaks from the heart (and head), and it has addressed many of our concerns. Thanks. I’ll start following Sarah’s Away Together blog, too.

  • Sarah, Great article and I couldn’t agree more- especially with kids. Living in London for three years was was a lesson in itself so living in a place and/or passing through are completely different experiences. Americans tend to want to see it all and say they saw it all… That is not experiencing it to its fullest…. My view on this really started when I lived in Seoul for two years as a teenager. I learned so much more by slowing down and experiencing the “culture”. Going places you aren’t supposed to go are always on my to do list when traveling abroad.
    .-= Chris Becker´s last blog ..Good Calories Bad Calories =-.

  • Fantastic tips. one of the problems of overplanning, as well, is not taking into account people getting sick, needing time to rest and be quiet for a while, and of course (for us), time to work while we’re on the road. we’ve had trips that have been WAY overbooked and really didn’t have much fun. now we try to schedule as little as possible and just hang. love this article -thanks!
    .-= jessiev´s last blog ..Myrtle Beach MayFest – a Month of Free Concerts and Festivals =-.

  • Hi all,
    Thank you so much for your positive feedback on my post! I’m also happy Christine chose a photo to use — the second one, of Cinque Terre on the Italian coast — that shows exactly where we’ll be staying in a couple of weeks. We’re renting an apartment in one of those buildings pictured.
    I’m looking forward to checking out the blogs linked in the comments above.
    thanks again,

  • Hi Christine & Sarah,
    thanks for the tips, funny enough some of them apply even for short vacations with friends when the planning and the “must-see” spots become killers 🙂

    I was wondering, did you ever run across
    While your family may not need to be hosted, still it’s a great way to get in touch with locals and find people that want to know people and show them around.

    I just used it in my last trip to Miami. I contacted someone to get suggestion about where to dance Salsa and I ended up having a great tour in Little Havana away from touristic spots and with really super-friendly locals!!!

    .-= Daniele´s last blog ..Hosting a stranger/Ospitare uno sconosciuto =-.

  • Sarah,

    Wonderful post! I think many of your insights are just as relevant for a 3 week trip as they are for a year round-the-world trip.


    (Sarah has nominated a number of her favorite small, locally owned hotels from around the world on – original accommodations for budget-minded travelers.)
    .-= Michael´s last blog ..Ten Popular Bloggers and Their All-Time Favorite Digs =-.

  • Great post. You do a really great job of calling out most people’s attitudes on long-term travel (or even, in some cases, shorter trips). I know I would find myself thinking a lot of these no-nos. The post does a great job on showing people why this kind of thinking can make your trip a lot more stressful. Keep up the great posts.

  • Thank you for this article, I really like the headings in quotes, that kept my interest 🙂 And the photos are fabulous, where is the second photo? It looks European?
    .-= The Dame´s last blog .."Develop an attitude of gratitude, and give thanks for everything that happens to you, knowing that…" =-.

  • Great article. So glad to hear that it’s ok I don’t have the whole year planned for our rtw family trip starting on July 31.

  • Very enjoyable post. You are right about trying to plan too much. It kills the fun and spontaneous feel of your travel. I say figure out the basics and let the rest work itself out.

  • Absolutely perfect! I agree with every point made! We are traveling on bicycles with our (now) 12-year-old twins and we find the slow pace of travel is great. We take lots of days off as the very act of packing up and getting on the road is stressful if done too often. We’ve also discovered that cities are not the best places to hang out with kids – they are so much happier in the small towns where they have free reign!


  • Our family is nine months back from our year of living in Spain and traveling around the Mediterranean. All of your points are so great and true! I finally embraced the idea that we couldn’t see it all, but that gave us reasons to go back!

    The planning or not planning is such a hard balance. I did learn though that whatever you expect and plan for… it won’t be that way so you have to go with it.
    .-= Dee Andrews´s last blog ..Discovering Love in Barcelona =-.

  • Wow – so true. We basically have an overview of what we are doing on our travels through SE Asia (for example, Feb = Bali, March/April = Malaysia, May = Thailand, June = Vietnam, July = Cambodia/Laos, August = China/Hong Kong). Although we don’t really plan any specifics too much more than a week or two out.

    It does mean that my wife seems as though she is continually researching where we are going to stay next, but it does mean that we change change a plan pretty quickly and with minimum fuss. Last week we were supposed to fly to Bangkok, but with all the issues there we decided to hang out in Malaysia for an extra week and fly straight to the Thai islands in the south rather than visit Bangkok. Easy to change our minds, but you also have to accept that sometimes at the last minute your plans can go awry.

    For anyone who is about to start planning their family travel this is some pretty good advice.

    My theory is – work out the big picture, what countries and things you have to do and then work out the finer details a little closer to the actual date.

    And most importantly have fun, doing it…

    .-= Colin Burns´s last blog ..Kuala Lumpur (again) and Melaka – our Malaysian Family holiday continues =-.

  • My husband and I are on a 6 month trip through South America and Australia. I can definitely relate to many of your points (although we don’t have children). Thanks for your great wisdom!


  • It’s good if you keep yourself updated with the latest happenings around the world specially on the place you’re visiting to avoid getting into trouble when you get there.