You don't need another checklist
Two simple questions to ask yourself when planning your next trip.
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.
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.
I consider myself an "urban tourist" since I love exploring new cities and neighbourhoods and really experiencing what life in that place would be like if I lived there. That is fun!
I also like going to those must see spots, maybe out of FOMO, or just because I have the opportunity to be there, so, why not! So having a sandwich from the Antico Vinaio situated just behind The Uffizi Gallery in Florence was an experience and doing so at around 6:00 PM on a Tuesday in February was exactly the right time to do so, for precisely the reasons that you mention in your Greece experience - there were no crowds, no lineups, I got to talk to the sandwich maker and try a few different "samples" and take a few pictures without getting in anyone's way. So those normally crowded places can be enjoyed without the discomfort that you might normally associate with those locations. I've had similar experiences at The Accademia, viewing The David, at the Pitti Palace, experiencing the royal apartments and in other locations and famous places in Vietnam, Peru and many other countries and cities around the globe. My idea of a great afternoon is to get lost in a new neighbourhood, in a city that I'm not overly familiar with, and, at some point, just siting, with a cold or hot drink and watching the world go by and really seeing what life looks like for locals and visitors alike.
The other side of travel is my experience visiting the Val d'Orica region of Tuscany last March. Rather than going from town to town and walking the streets or touring through local landmarks, I was treated to half a dozen amazing experiences that I would not have had as an urban tourist. At the same time, I was able to spend time in several amazing Tuscan towns, including some that are not likely part of most itineraries. It was an special and unforgettable experience that created new friends and incredible memories.