Let Me Explain: Planning Every Second of Your Trip Is Costing You, You Need to Loosen Up

I travel as frequently and for as long as I can every year and I’m always coming back with stories so silly and unbelievable that I wish I could write a book about it. I love recounting every detail of my trips to my friends and they always ask how I have such incredible experiences.

Once in particular I was telling a friend about all the phenomenal people I met and the wild adventure that was getting lost on a castle grounds in Sintra, Portugal to two friends who had been there mere months before me. They told me how much they disliked the visit and how they wished they would have chosen elsewhere to travel. I was perplexed by this statement because I fell in love with Portugal and plan to go back in the future. When I asked why they didn’t like it, they said they felt it wasn’t all that different from other parts of Europe they had been to, despite packing their itinerary full with all the popular landmarks, food destinations, and attractions.

That’s when it dawned on me.

They didn’t dislike Portugal at all. They disliked their packed itinerary that left no room for being spontaneous, wonderful mishaps, or wandering off the beaten path. Having every minuscule detail of their trip cost them even the possibility of having a unique experience. Let me explain. 

Now as someone who runs a travel website, Substack, and sells itineraries for a living, I’m not going to sit here and tell you that you don’t need an itinerary. YOU ABSOLUTELY DO. At the very least, you need a general idea of what you want to do and see before leaving your accommodation each day in order to walk away from the trip with fulfillment. But - and there is a but - not every moment of your trip should be accounted for. When we over plan or refuse to budge, we end up not meeting the cool girl at the pub crawl who invites you tag along with her on her day trip or the funny guy who insists you go with him to see DJ Sammy Virji in the middle of Montreal with a mere hour notice (yes I did both of these things and yes it made the trip worthwhile).

If You Needed Permission to Dilly Dally, Here It Is

So if you take anything from this post, I hope it’s this: leave room to dilly dally, to wander, to be whimsy. Be okay with being flexible if something better comes up or calls to you. Leave space for the unexpected to happen because nine times out of ten it will and you must be open to it. Truly some of my favorite moments out of my travels have occurred because I gave myself time to just explore and talk with the people around me. If this is hard for you, I would try reminding yourself that even if you don’t see every single thing on this trip, you could always go back. The city is not going anywhere and you have time.

The best parts of traveling are so often the unplanned bits, the random people, and saying yes to things you wouldn’t back home (within reason of course and while staying safe). I know my Type A folks are going to read this and physically and emotionally cringe so it’s okay if for starters you just leave an hour time block on your schedule to let your feet or a feeling decide for you. Slowly you’ll get used to leading with your heart every once in a while, instead of always your schedule. 

Expect the Unexpected Look For the Unexpected

Make the damn schedule, follow one of my itineraries - that have time set aside for wandering already embedded -  and hit all the spots that you consider a must see AND search for the unexpected in unusual places. I promise that you can do both and that it will be well worth it. 

Happy wandering, 

Raven