How Do You Plan?

Since we’ve been back in Pennsylvania, I’ve dived right back into planning for Europe. We leave for Scotland in exactly two weeks, and I’m feeling a little overwhelmed, but mostly excited. We have our flight to Scotland booked, our three-month lodging ready to go, and I just booked our tickets out to Croatia in September. We have a few big ideas in the planning phase. But I still wake up some mornings fearing that I’m not doing enough and I need to do more.

What do you do to plan your travels? Are you a spontaneous traveller who goes where the wind blows? Can you just show up to a destination and find things to do? Are you able to have the best time without wasting too much time thinking about it? When we went to Ireland years and years ago, we tried to do just that. We decided where we wanted to go, but didn’t decide what we wanted to do while we were there. We ended up walking around aimlessly day one, crying and arguing through day two and finally planning the rest of the trip on day three.

Do you meticulously plan every day of your trip? Do you make your A and B lists, assess costs, make game plans? This trip across country that’s what I did. I researched for days all of the places we were stopping, creating lists of all the things that sounded fun. We took these giant lists and turned them into smaller, more manageable lists (or rather, our A list). It ended up working really well, but we still missed out on some things. I think when in the planning process I reached a point where I threw up my hands and stopped, so we missed out on things like Ghiradelli in San Francisco and Chapel of the Holy Cross in Sedona.

I’m trying to find a good balance between the two for this upcoming trip. I know if I try to plan every little detail I’ll go insane. If I don’t plan anything, I’ll feel like I’ve wasted some serious time, both before the trip and during the trip. I’m trying to do it in stages, but sometimes I find myself thinking about the end of the trip instead of what’s coming up immediately.

How do you go about planning? Do you have any tips or tricks? How do you ensure your sanity and a great trip? I’d love to hear your thoughts!


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  1. I like to plan about 80% of my time and have ideas for the rest if I choose to do that, or just take time to wander and enjoy being in a place without an agenda. But I really enjoy planning activities, and I think planning also helps me be able to do the most things within my budget, since I know about how much things will cost and can think ahead about whether or not something might be worth it. But there are some types of trips I plan way less, like road trips, because there are too many variables to plan exactly – we have a few tickets for things like Alcatraz and skydiving that will sell out, and it took a really long time to figure out what date we should buy it for within our 3 week trip.

    1. I LOVE the idea of planning 80% of the trip! To me, that sounds perfect. You have structure and security in your day-to-day activities while still ensuring you have time to be spontaneous.

      I can’t wait to hear about your skydiving! That’s so awesome!

  2. I didn’t realize you could leave comments but space bags FTW. They’re fantastic for clothing. The only downside is once all the air is out, the bags are kinda heavy so be careful! Hope finalizing is going well!

    1. Space bags!! I remember you telling me about them and thinking that I need to buy some! Failed at that though… Which means I’ll just have to buy whatever doesn’t fit, right??

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