To Plan Your Trip or Wing It: The Great Debate

If I were to describe my travel style six years ago when I first started traveling, it would be winging it. Hard core winging it. Buy a one-way ticket, get an idea of what you want to do, and see where it takes you. When I bought my one-way to New Zealand four years ago the only plans I made in advance were one couch-surfer to stay with for two days with an entire year of traveling ahead of me. Southeast Asia was the same, minus the couchsurfer. I didn’t have to be anywhere, so I didn’t give myself anywhere to be. Why plan your trip when your trip can plan itself? The freedom you have when you can choose to stay or to go, when no plane tickets or hostel bookings force you to leave a place you love, is both spectacular and ineffable.

But the older I get, the more I have begun to love having plans. And even more so, I love making them. When I went to Italy for 8 days last October we had every hotel booked in advance and bought only the train tickets while we were there. I scoured every travel website for every bargain and the whole trip was one smooth ride. We were tourists and I was totally OK with that.

florence italy tourists map

yup, we’re tourists!

A lot of backpackers look at plans and group tours and organizing transport in advance as the safe and boring way to travel. If you’re doing those things you’re a tourist, not a traveler. And I guess I used to share the same elitist attitude. My free, adventurous spirit needed to explore without boundaries and take every 10-hour local chicken bus to feel like I was really getting to see a country.

But somehow, since my magical “I turned 30” switch was activated, my opinions have quickly shifted away from that mentality. Don’t get me wrong, I love the color and excitement of local buses and open-ended trips. I still have a lot of backpacking I want to do. But now I have a husband and a job and our trips have to come in smaller packages. When you only have a week or two you don’t want to waste a whole afternoon trying to figure out how to get to the next place (or even what that next place will be) or spend 10 hours on the local bus when there’s an 2-hour minivan ride for $10 more.

On that trip to Italy I took the first guided tours of my entire life, save for maybe some museum field trips of my youth. While I begrudgingly accepted my fate I soon realized just how valuable these tours are. The guides know way more than I ever could, and they offer conveniences and insight you just don’t get when you’re sorting things out for yourself. Did at scoff at the €35 charge? Yes. Was it worth it in the end? Completely.

I’ve always firmly believed that most travelers have one of two things: time or money. As long as you have one or the other, you’re fine. If you’ve got neither, you’re pretty much fucked.

So maybe I’m not really a traveler anymore, but just a person who loves traveling. And maybe a guided bike tour including accommodation and round-trip transportation from the airport through the Chocolate Mountains of Bohol in the Philippines sounds lame to all those trail-blazers out there busy hacking through uncharted jungles with a machete, but it sounds pretty nice to me.

tulum mexico beach bar

plans are for planners.

I guess the way I see it, I already blazed my own trail and this is where it got me. I blazed my trail across six continents through love, loneliness, friendship, adventure, poverty, and homelessness to realize what things are most important to me when traveling. So I do my research ahead of time, I book as many things as I need to to make my abbreviated trip run as smoothly as possible, and I disregard the opinions of any travelers out there who will scoff at what a tourist I am. Cause you know what, with only two weeks in a place you can’t be anything but a tourist. So give me my fanny pack and Hawaiian shirt because if I can’t see a whole country in a week, I’m certainly gonna try to see the best of it. Just like everyone else.


  • elo says:

    can’t remember how I fall on your blog but it’s a great one 🙂
    I totally agree with what you were writing on that post :
    -the older you get, the more organized you get
    -once you start to travel with tours, you change from traveler to tourist
    but at the end, are you not a tourist everywhere in the world except where it’s home for you ?
    I’m now on the road since more than 17 months and is that because I took a job, which make me stay at the same place for a while, or because I get older, that I got the feeling to be tired to choose everything at the last minute ? I am going tomorow on holiday and because of the time, and to change a bit, I choose to plan and reserve everything, let’s see how it will go…
    But at the end, even if we got 2 days or even one afternoon, this feeling to be free of our future, because we choose to take a bus, just like that for example, and to see, where it will bring us, because we like to discover our “home” in an innocent way, that feeling for me bring us the magic and the beauty in our life.
    And I think once we get older, we don’t see anymore the point to see the all country and to be proud to be able to see I went to Cambodia (which means I saw the all country), but we kind of like more on to appreciate the time we have on our journey, to rest ourselves in the same way as to discover a new country/culture, no ?

  • jennifer says:

    I am an over planner. I like being an over planner. I am traveling on time off from work. Sure, I could go away and leisurely wake up and decide then what I am doing that day. But I don’t want to. I want to arrange things so that I make sure I see everything there is to see without wasting any time figuring out when I am there.

    Plus, it makes the time leading up to a trip that much more enjoyable because I get to see what it is I will be doing.

    • Taylor says:

      I’m right there with ya Jennifer. People traveling indefinitely have a lot more luxury when it comes to figuring stuff out as they go. When I’ve only got 3 weeks, I’m gonna jam pack them with all the best stuff I can find. And of course plan in a few relaxing days as well. It is a holiday, after all.

  • Dave Briggs says:

    I used to completely wing trips, but after each one, I would look back and think “Why on earth didn’t i do that?!”. Of course, its impossible to see and do everything, but just a little bit of organisation means that you should see the highlights of a country you may never get the chance to return to again.

    • Taylor says:

      I’m telling you Dave, the day I turned 30 it was like “hey, planning makes a lot of sense!” This way, when I get there I don’t spend half my time figuring out what I’m doing. Ahhh, the careless joys of youth.

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