top of page
  • Writer's pictureAnne McCormick

Travel Tips for Under-Planners

You’ve landed in a brand new place. The air is full of a mysterious language and even more mysterious smells. You can taste freedom and adventure… now what?

If you’re an under-planner, this is a familiar question, and it’s not necessarily an unpleasant one. Under-planning can lead to magical, whimsical experiences as you let the wind blow you in whatever direction feels right– into a hostel recommended to you at the local watering hole you happened upon or onto a bus that rumbles you through the countryside to a town you didn’t know existed.

As Paulo Coelho said, “Travel is never a matter of money but of courage.”

If all of this sounds familiar, then you might be an under-planner! Be proud of this. It means you really grab life by the horns and live in the present moment, and many people struggle to do this.

However, there are a few major downsides of under-planning. The biggest ones are:

• Stuff often costs more. Under-planners, by showing up on a whim with no concrete plans, often end up paying more for everything from transit (too bad you didn’t learn about that cheap travellers pass you had to sign up for two weeks ago), to accommodation (the only hotel with a room is at the fanciest spa in town!), to experiences (it was fun snorkelling, but you found out later it was triple the price of the place down the street).

• You can miss out on the best stuff. Some things need to be booked in advance. If you want to travel to that distant island, or attend a healing sound bath experience, or book a trip into the middle of the desert to see some amazing rock formations, you might be s*** out of luck if you wait until you get there. Under-planners are charming enough that they can often talk their way into things, but just as often lament about not booking important experiences beforehand.

• It can get boring. Under-planners flourish during extended, months-long holidays but struggle with short ones. An under-planner may travel on that rumbling bus to a new town only to learn that there isn’t a lot of stuff to do there. This is fine– if they're a particularly creative and extroverted under-planner, every place holds opportunity for new adventures. However, if they're only there for a couple of weeks, every day matters. Under-planners can end up wandering the streets aimlessly and then have to take precious time from their holiday to do some research-on-the

-fly, which can be frantic and disheartening.

So, the next time you book a flight and stuff some clothes in a sack:

Do the research. No, you don’t have to plan every moment of the day like your over-planning friends. You’re onto something magical here– you have a natural talent for tapping into what travel is all about, which is exploration, curiosity, and courage in seeking new experiences outside your comfort zone. Don’t let that go.

Instead, your research should simply be a framework that you can fill in as you go. Make sure you’ve answered simple questions like: Do I want to go somewhere new every day, or do I want to find somewhere magical and explore that area for a while? What are my favourite forms of exploring, and do I need to look into expeditions or bookings for these? Is there a major festival going on/is it tourist season and should I book reputable places to stay now so I don’t end up in the honeymoon suite, or is there room for improvisation?

Flying by the seat of your pants the right way takes some work. Find what tethers you to your ideal holiday– maybe it’s a location (“I’ll be there for five days and leave those open for anything!”). Maybe it’s a favourite hobby (“I want to hike up these three mountains”). Maybe it’s desire to spend some busy time in urban areas and some quiet time in rural areas drinking the local wine. Maybe you’re a shameless foodie and your travels will take you to food destinations.

Once you have your framework and your tether, you know you won’t waste time and money, and you'll have a foundation of security that allows for even greater freedom and flexibility. Go forth and explore!

Learn more about my Custom Group Experiences! Groups are hard to plan for because they often have under and over-planners in them. To fulfill everyone's desires and ensure that everyone feels safe, I help plan your logistics, book accommodations and experiences, and offer transportation services. Everyone in your group will feel accounted for– including you, my dear under-planner, as you wander off by yourself for a while following a trail of possibility.

10 views0 comments

Recent Posts

See All


bottom of page