Travel and the Power of Letting Go: Santorini, Greece

There are two types of travelers in the world: planners, and non-planners. I know people who are most comfortable planning every detail six months in advance, or more: where they’re going, where they’re staying, what they’ll be doing for side trips, and what they’ll be eating.

Me, I like to take my chances.

Donkeys give rides up Santorini’s intimidating steps to cruise ship passengers. Photo by Charish Badzinski

It wasn’t always that way. I was definitely a planner when I first began to travel. There’s a lot of fear that accompanies leaping into the unknown, and planning is compensation for fear. I overpacked. I made reservations well in advance. I bought expensive guides to the places I intended to visit.

Then, I went to Santorini, Greece.

The ferry from Piraeus to Santorini. Photo by Charish Badzinski. 

I boarded a ferry from Piraeus to Santorini, knowing little about where I was going, and making the entire trip without any reservations. The thought of disembarking to a crowd of shouting hoteliers barking out their nightly rates and locations thrilled me. I stood on the deck of the ferry, letting the cool Aegean breezes wash over me, looking into the great blue beyond, and wondering what adventures awaited me. Knowing whatever they were, they would help me grow. Knowing they would give way to great stories. And knowing, no matter what, things would be okay.

On the ferry. Photo by an innocent bystander.

When Santorini rose before me, baring the layers of her history and rising in a cliff, my heart caught in my chest. Once in port, there they were – the hoteliers. It took only a moment for me to get a room near the caldera for 35 euros a night, with a ride from the port, and a return trip for my departing ferry.

Hotel pool and view. Photo by Charish Badzinski.

The room was sublime. New hotel. Soft beds. The kind of view that makes you marvel that there are people in the world who wake up to this splendor every single day.

Beautiful Santorini. Photo by Charish Badzinski.

But the greater lesson was this: that in giving up my need to control my travels, I freed myself up to anticipate the unknown, and welcome an experience I never saw coming. There is incredible freedom in not knowing every step before you take it, and in trusting that you will know the right step when the time comes.

I’ve gone to the dark side of not planning, and though I’ll toe the line from time to time, there’s something about not knowing that has captivated me.

What have your experiences been with planning or not planning?

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Charish Badzinski is an explorer, foodie and award-winning travel and food writer. When she isn’t working to build her blog: Rollerbag Goddess Rolls the World, she applies her worldview to her small business, providing strategic communications, media relations and writing support to individuals and organizations. 

Find Charish on Twitter: @charishb
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Rollerbag Goddess Rolls the World by Charish Badzinski is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License.
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