an itinerary showing travel bookings

Original photo by Ashley Rehnblom.

You’re going on vacation and you’ve booked your flights, overland travel, and all your accommodation. You’ve scheduled tours to guide you through the sights and you’ve planned out all the stuff you’re going to see on your own. You’re so organized you’ve even figured out where you’ll be eating breakfast, lunch, and dinner each day of your trip and you’ve contacted some of the restaurants to make reservations. You’ve basically made bookings for as many things as you can to save yourself the stress of doing it on the go.

Seems like a great idea, right?

Well, yes and no. While it’s true that there’s some peace of mind that comes with knowing you’ve got a nice place to stay or the exact flight you want, pre-booking everything locks you into those plans.

Travel is full of the unexpected – both good and bad – and it’s best if you can keep your travel plans as open as possible in order to work around any surprises. What kinds of things could go wrong (or right, depending on how you look at it)? Here are a few:

1. You hear about an amazing place that isn’t on your schedule. This has happened to me a lot – I’ll bump into another traveler or a local that tells me about some incredible attraction or nearby town that I hadn’t considered visiting. Maybe it was too much of a hidden gem to be mentioned in the guidebook, or maybe there’s a special event going on – either way, it’s something amazing that’s worth taking advantage of if you can. Sometimes it’ll require turning your travel plans completely upside down, but if you’ve kept your itinerary flexible, it’ll be a whole lot easier to do.

2. You love or hate a place more than you expected. It’s normal to travel someplace with a preconceived notion of what it’s going to be like, but not all destinations live up to our expectations. Maybe you’ll find that bustling London (where you’d planned to stay a while) isn’t really your cup of tea after all, but that a coastal town you’d expected to breeze through has bucket loads of charm – and that’s where you’d much rather spend your time. Keeping your travel plans open allows you to extend or shorten stays as you go.

3. The weather doesn’t cooperate. It doesn’t matter that the weather forecast said it’d be sunny if the reality is that the snow is too heavy or the seas are too rough to do the activities that you’d planned. Make sure you leave yourself some buffer so that there’s time to go ahead with your boat trip, hike, surf lesson or whatever else, once the skies clear up.

4. You fall sick or get tired. No one wants to go halfway around the world and miss out on seeing what they came for because they got sick or ran themselves into the ground. Flexibility is the key to getting around this. When I got food poisoning in Europe, I extended my stay in a quiet town so that I’d have time to recover before continuing on to the more action-packed destinations. It was easy to do since I was booking my accommodation and transport as I went.

5. There are strikes or closures. If a museum or important sight is closed on the day you had planned to see it and you’re forced to hop on a train the next day, you have no choice but to miss that attraction. However, if you hadn’t pre-booked everything, you could have always changed your plans and stayed in the city an extra day.

6. You were overambitious with your scheduling. Maybe it takes longer to see everything in the city than you thought it would, or the distances are further than they appeared on your map. Perhaps you got lost wandering the streets, or your meals took longer than planned because service is slower than you’re used to back home. It’s also possible that you’re simply not as fit as you thought and needed frequent breaks between sights and activities. Whatever the case might be, the truth is that we are all are notoriously bad at estimating how long things will really take – and we tend to be overly optimistic in our guesses. So plan for the fact that a museum might take you three hours instead of two or that you’ll get lost in the winding streets of Venice and build that flexibility into your schedule.

If you’ve ever traveled before, chances are at least one of the things above has happened to you – they are really, incredibly common. Make it easier for yourself to work around unexpected situations by avoiding locking yourself into hotels and transport, in particular. It’s okay not to have all your plans set in stone. I know some people worry that every hotel, train, tour and activity will become booked out because they’re vacationing during peak season, but the truth is, unless you’re traveling during a major festival or event, you’ll rarely be stuck without any accommodation. It might sound scary – traveling without a whole bunch of confirmation numbers and reservation codes – but the truth is it’s surprisingly liberating.

What do you think? How do you normally travel? Do you pre-book as much as possible or prefer to fly by the seat of your pants?