My parents raised me to be a traveler. I’ve experienced almost as many countries as I have birthdays, and many of those trips were with family.
My mom takes planning a trip to the extreme, filling a binder per trip with daily itineraries and pre-purchased admission tickets and Google Maps printouts and Rick Steves city guides. I learned from her that traveling was a lot of work on the front end and that deviating from the plan equaled stress and frustration–but following the plan meant eating at amazing restaurants and getting to see all the sights.
Matt, on the other hand, hates plans. When we took our cross-country road trip, he wanted to drive until we got tired and then just find a motel and crash.
Visiting this bar with a windmill on top was a spur-of-the-moment decision, and it was so much fun.
And because I was raised on travel binders and hour-by-hour agendas, the roll-up-to-any-motel idea was not gonna happen.
So we compromised: I’d book our lodging, and we’d have a general idea of landmarks we wanted to hit along the way, but we were flexible to make additional stops or skip a sight with a long line. It worked really well–he appreciated that my planning meant staying with fun friends or in cool locations, and I found our spontaneous detours adventurous and exciting.
In Amsterdam, we took a similar approach. Matt booked hostels for us to stay in, and I wrote up a list of 5-6 things we might want to do in the city over the week we were there, and we figured out the rest as we went.
Sometimes, traveling without a specific itinerary means you don’t experience everything you potentially could. We never made it to the Van Gogh museum because we kept pushing it to later, tomorrow, Saturday–and then it was too late. Without planning, you also miss out on magical money- or time-saving opportunities (like skipping the lines at the Anne Frank House) that make the trip go more smoothly.
But traveling flexibly has its benefits too: you can take a walking tour on a day when it isn’t raining, stumble into cute cafes where you have the best croquettes and Dutch pea soup, or even spontaneously get a tattoo (if you’re Matt and me, anyway).
It’s all about balance.
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Victim to Charm 
I used to be much more spontaneous about travel. But, having a disability and requiring assistance from others means I must plan everything now.
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That makes sense–any sort of necessary accommodation requires planning.
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Love this post and totally agree. I feel like the best things in life–and in travel–are often spontaneous, spur of the moment decisions; in general, I am a very go with the flow type of person. That said, planning out a trip can be so rewarding and can make for less of a headache in the long run. I agree, balance is everything!
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Balancing it is truly the most important. Leaving yourself flexibility is crucial, but having a general plan means you can take advantage of more.
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I usually go with the “compromised” version :)
We plan our trip – the places and deadlines and books the rooms, but the visiting on the spot depends on our mood, the weather, etc. We might go all day long doing nothing, or we might visit all there is :)
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Love it!! That’s the way I like it too.
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Yes, I’ve discovered the joy of balance in this aspect, too. I love the planning stage, but I’ve also learned to value having enough flexibility to change plans or just wander. I’m not too into the “find a hotel wherever we are” either but there are some great apps for that now, like HotelTonight and lightning deals with Airbnb, if it ever strikes your fancy. Once, we scored a fabulous Times Square hotel for almost nothing thanks to HotelTonight. :)
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I didn’t know about HotelTonight! That’s good to know for an sort of SUPER spontaneous trips I do.
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It’s pretty sweet! Especially in a big city, where you know there will be rooms no matter what. On the few occasions I’ve tried it, it’s been a fun experience.
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Yes, we compromise, too. It’s a good way to enjoy the holiday with some certainties, like accommodation. Do you have any must-see, must-do for my Amsterdam list? I’m going in 8 weeks!
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Yes!! I LOVED the Versetzmuseum (which is a bit obscure in the museum loop), Anne Frank House (a classic must-do), walking tours of the city + Red Light District specifically with Sandeman’s tours, and Vondelpark if the weather is nice. I also recommend wandering around and drinking hot chocolate everywhere :)
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That’s just regular hot chocolate, right? 😜
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Yes! But more delicious than we have, I think.
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