The Spirit of A Place :

You don't need another checklist

Two simple questions to ask yourself when planning your next trip.

October 15, 2025

A few years ago, I went with my husband and kids to the Greek island of Andros.

I wanted a place that was brand new to me, somewhere I could walk from home to the beach and that wasn’t overrun with tourists. I’d knew I found it. We were almost alone on this beach, and it felt like the world had paused for us.

Empty Vitali beach in Andros, Greece

We decided to intentionally skipping Athens, although none of us had ever been there.

Right before heading back to Italy, though, we felt the pressure to visit the Acropolis. I mean, can you really go to Greece and not see the Acropolis??

So we went. The heat was scorching, and we, along with thousands of others, were herded through a narrow line, like cattle, while security people waved their arms to keep the crowd moving.

Was the Acropolis stunning? Yes.
Was it a great experience? Definitely not.

I don’t think I even took a picture. It was underwhelming, and somewhere in that slow shuffle uphill I was like Why on earth did we do this?

The day before, we’d been driving in Andros down a small country road when we noticed a tiny white and blue church on the side with this giant tree shading its entrance. We stopped, went inside (the door was unlocked), and when we came out my toddler started playing chase around that majestic tree.

It was a moment of lightness and bliss, the kind that stays with you years later.

It really made me think about how easy it is to fall into the trap of what we must see (especially by social media).

Maybe the trip to Tuscany that you’re imaging and dreaming of doesn’t need another checklist.

(and trust me, if you skip the “famous” panino at Antico Vinaio or the Vivoli affogato in Florence, you can still have an incredible experience!)

Instead, ask yourself.

What do I really want from this trip, and why?

Maybe it’s connection. With your family or your friends. Maybe is inspiration or reconnecting with your roots.

What kind of feeling am I longing for?

Your answers will guide you far better than your checklist.

Originally published on Giuditta's Substack
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