My Love-Hate Relationship With Planning


I love my details. I love knowing open hours and locations of the attractions I’m interested in, putting all that information on an Excel sheet, and planning my itinerary around that info. I love knowing that it’ll only take 15 minutes to walk from one place to another, or that a metro day-pass costs about 10 USD, that you don’t need a visa to get into whatever country, how much a ticket to the museum costs, how much I’ll probably spend at a restaurant, and when the free tour starts all before I step foot on the plane.

You know what I hate? Planning. It takes forever. You need to leave enough time that you’re not rushed but not so much time that you have “nothing to do” for two hours. You want to immerse yourself and take in the new sights, but you don’t want to wander for the whole day. Striking that balance and trying to stuff everything you want to do into a matter of days is… is not fun.

I know that what I do isn’t exactly normal, but I didn’t think it was all that weird either. But I started working out the details for an Asia tour for February/March 2018 yesterday and when I asked my sister to help (since I’m going with her), she said my planning drives her crazy. (She did end up helping though. Because she’s awesome.)

Preliminary flight planning.
All I did was ask her to help look up prices… I’m the one that had to type out the 24 different flight paths.

So do I generally spend a shit-ton of time on planning? Yup. But I like to think of it as an investment: I save our group time by getting rid of stupid questions (“Where should we go next?”) and as you can see above, I’m saving ~$570 potentially per person.

Rough notes for Montreal.
Rough notes for a trip to Montreal. I didn’t even include the hours. Livin’ on the edge and all.

And then in case you couldn’t tell from my master travel packing checklist, I’m cautious of emergencies. I like having hard copies of everything: flight info, hotel info, emergency numbers, credit card numbers, credit card company phone numbers, check-in and check-out times, conversion rates, whatever. And then battery packs, emergency cash, the usual. Having everything in my back pocket makes me feel better.

See also: Tips for Packing Light.

It’s also kind of necessary for groups. I had no problems during my month in Europe and I only had a rough path itinerary that I drastically changed and altered along the way. I didn’t have any plans for any of the cities I hit and generally relied on a hostel map to get me around. But with groups, you get conflicting opinions, varying budgets, and wildly different ideas of fun. One person might like museums, another might like beaches, and yet another might prefer events. And then you get the one-hour discussions on what to eat, where to go next, how to get there, and when to go where. (I wish one-hour was an exaggeration, but it’s not even a maximum.)

And it kind of gets me pumped up. Like “Wow, this is happening, I’m going to see [insert cool thing here].” Having to look up all the numbers and locations and prices makes it that much more real. Budgeting and starting to save up makes it that much more real. Sometimes (rarely), I spend all that time planning just to get excited and end up not using the information. It’s just so easy to get wrapped up in it.

See also: Things to do in Bologna, Italy.

Just wanted to share. Do you generally plan or do you usually wing it? Do you like to plan? Do you like winging it? Let me know in the comments below!

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