Why I Over Plan My World Travel

My first trip to Europe in 1998 was an organized educational excursion for class credit. The experience was vastly different from my second trek, a year later, when I grabbed a backpack and a Let’s Go Europe book and took off into the world with my college boyfriend without a plan.

Well, we had a loose plan. I was living in Colorado and we were going to take a trip home to Philly, but we found $350 tickets to London and decided to purchase those instead. We also wound up with a $75 round trip ticket to Amsterdam and a rail pass that was good for the Netherlands, Belgium and Luxembourg. We explored them all. But not easily. Here are the mistakes we made.


As a free spirit and an aspiring world traveler, I wanted to let the experience take over—so I didn’t book accommodations in advance. I figured, if we liked one place, we could stay longer, if we didn’t like another, we could quickly move on.

This was about a year before many hostels were set up for online booking, so it was more complicated to find accommodations at that time. We got to London and immediately booked our first and last nights (at a dumpy £100 a night hotel). The we showed up in Amsterdam with a map and a list of hostels in our guidebook. It was March, the shoulder season, and we didn’t expect hostels to be full—but they were.

We walked from hostel to hostel, and the front-desk staff at each one told us they were booked. We called budget hotels (on a pay phone), but they were full, too. We aimlessly wandered the streets, with our backpacks getting heavier and heavier and our legs getting weaker and weaker. Finally we decided to use the rail pass and get the late night train to Luxembourg. We could sleep for a few hours on the way.

But when we showed up at the train station, we discovered that that last train to Luxembourg had already departed for the night. I had read the train schedule backwards 🙄 So, feeling like we had no other choice, we took the shuttle back to the airport, and using our backpacks as pillows, we got some cautious sleep in the waiting area.

The next morning we hopped on the first train to Luxembourg, and though we couldn’t find any hostel beds there either, we found a cheap hotel with a spacious and clean room, and we luxuriated in the comfort for a night.

We had a wonderful time exploring Luxembourg 🇱🇺 and Belgium 🇧🇪 and when we made our way back to Amsterdam, we finally found a room for $25. We had a private room and a shared bath and strict rules about when and how long to shower and when to show up for breakfast. But we were so happy to have a place to stay.

That experience shaped my travel style. From that point on, I’ve always scheduled my accommodations and ground transportation in advance. And on my most recent trip to Amsterdam, 20 years later, I was glad! This time, hoards of travelers made the city almost unbearable—even in the shoulder season—so I can’t imaging showing up without a plan.

But I still think it’s important to leave a lot of free time in the schedule for wandering, getting lost, and letting the moment take you where you need to go.

How do you like to travel? Are you a planner or a wanderer?

~ LiAnn

3 responses to “Why I Over Plan My World Travel”

  1. Yay! Another over-planner. I’m not the only one!! Actually, it kinda depends. Overseas travel always includes prebooking hotels. Sometimes on road trips to the western US, however, we wing it. We pull a little 12-foot travel trailer and we just look for a campground and hope for the best.
    Reading about your first European experience I thought, “Good grief. How did we get by without the Internet?”

    • That’s funny, we will wing it on a U.S. road trip, too, but never for international travel. I remember the first time I used the internet to book a hostel in Scotland, I still had to get a bank check in pounds and mail it to the hostel. My, how things have changed!

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