(Leave your question for Brandon here!)

Should I schedule most days of my trip or let it be more spontaneous? What’s a good balance?

-Tracy Charles

Dear Tracy,

How we plan travel is often reflective of how we approach the rest of our lives, and few of us want to be told how to live—so, while this may seem a simple a question on the surface, I’m impressed that you asked. To some extent, it’s fair to say your trip should be structured according to your own personality. If you’re a hardcore organizer who lives by schedules and lists, you might find yourself in a panic on day two of a trip with no list in hand for the first time in your life, and this isn’t the time to bring on an identity crisis by dramatically challenging your most fundamental traits!

But don’t worry: I’m not going to shirk your question by insisting the answer depends on who you are as a person, because I think there are some universal truths about travel we all can apply here.

As in many situations, the middle ground is the best place to start. When it comes to travelling, you usually have a few upfront ideas of what you want to see, eat or do in the place you’re headed, and you do want to secure those in your plans so you don’t miss out on the reasons you journeyed there to begin with. How rigidly you schedule these items, though, is another story.

If there’s a restaurant you’re dying to try, check ahead and see if reservations are recommended. If so, you’ll clearly need to schedule this at a specific time on a specific date, and work the rest of the day around it. Seeing something like the Eiffel Tower doesn’t require such stringent scheduling, but, if you want to climb it, you’ll need to do that during opening hours, so check ahead to make sure you don’t arrive ten minutes after last entry. If you’re in Siem Reap, you undoubtedly have trekked here to experience Angkor Wat, and a little research will uncover that you really want to be there before sunrise for a humbling spectacle, so you’ll need to schedule that carefully.

Are you catching on to the main point here, Tracy? Researching ahead of time will reveal how carefully you need to schedule the big things you’re intent upon experiencing. Check ahead, and schedule what you must. And don’t forget to look into transportation! Getting to and from the things you came for may only be possible at limited times, so do read bus/train/ferry schedules in advance and adhere to them carefully. Without them, you may end up spending your entire trip sitting on your backside in a park (which could be great, in my opinion, but maybe not in yours).

Beyond serious time constraints like mandatory reservations, transportation schedules, and operating hours, try prioritizing, not scheduling. Rigid scheduling adds unnecessary stress to your trip. You don’t want to waste time being upset that you’re 34 minutes behind schedule and spend the rest of the day playing catch-up instead of remembering to look up at everything around you.

I suggest two lists:

1. Rank the things you want to experience in order of importance to you. If missing something will make you cry the entire way home, put it at the top of the list. If you think something would be cool to see, but your life wouldn’t be ruined if you missed it, add it to the bottom. Don’t stress too much on this; you’re not going to go down the list in order, so just because something is at the bottom doesn’t mean you won’t see it. Try to jot this down quickly, going with your gut feelings.

2. Take all the items on the list above and group them by geography. Things within walking distance of each other, or in the same general neighbourhood, should be put into clusters. The order of groupings doesn’t matter, but include each item’s rank from the list above when jotting down your groups.

If you take a look at your geographical groupings, you’ll get a fairly simple picture of which areas of the city to head to first. Which groups have the most high-ranking items in them? You might want to head there first and conquer the biggest chunk of your list in one shot, leaving you open to pick and choose which other items to visit.

Notice I haven’t suggested adding these to a schedule with times, or even dates, to visit. You simply don’t know how long you need to spend anywhere, so isn’t it a little brash to assume you do? You might find that Big Ben doesn’t really hold your interest for more than 5 minutes, or that you can’t pull yourself away from the Taj Mahal as quickly as you thought. Don’t sabotage yourself ahead of time by assuming you’ll spend a half hour at each.

I don’t recommend planning which day to see things either. You don’t know what the weather will really be until you wake up each morning, and that may dramatically affect things like outdoor activities, or items you want to photograph in beautiful sunlight. And, if you’ll allow me to give a more extreme example, I once found that after two days in Venice, I saw what I came to see and was ready to go, so I left early and headed to Verona for the rest of the time I allotted there.

That kind of flexibility may be beyond some people’s comfort level, but my point is that you can’t be sure how much time you’ll want to spend experiencing one thing, or even one area, so don’t try to schedule yourself into traps. Leave as much flexibility as you can, prioritizing top choices and then filling in free gaps with other places of interest.

When you leave yourself open, to any degree, you not only allow yourself to spend the right amount of time for you at each spot on your list, but you leave yourself open to experiences you didn’t even know were options. Give your destination a chance to surprise you, and inform you. You’re probably not an expert on this destination already, so how could you know ahead of time which experiences will be best for you?

Be willing to investigate on site, not all in advance, and follow the guidance of people you meet along your journey. If you couldn’t resist over-scheduling in advance, then at least be willing to crumple the list and go where your heart takes you when you find it. That’s where you’ll find the magic, and that’s why we travel.