I always thought I’d go to Italy with friends or a boyfriend… or my imaginary husband on our imaginary honeymoon. But as time went on it began to tell a different story. I decided that as an empowered Single Lady I’d take myself to Italy for my 40th birthday. But then I was diagnosed with cancer and that was that. So this year– a week before I turned 41– I woke up one morning and, like a woman possessed, I popped open my computer and put into Google: “Woman traveling alone to Florence in November.”

Up popped a blog, A Girl In Florence by a super cool-looking chick named Georgette, who moved from Texas to Florence several years ago. Something about her story spoke to me, and without overthinking I quietly booked a ticket to Florence before I had even gotten out of bed, and before I had a chance to let anyone talk me out of it (aka: before I could talk myself out of it.)

Some people go on “vacation,” but I tend to hold out till the last second and then go on “life-altering, skip the needle on the record journeys.” And this was a time I knew I needed Italy to be the motherload of cosmic shifting.

There was only one issue. Having traveled most of my life I have developed a pretty extensive “I can’t ____ when I travel” list: I can’t walk around looking at a map like a tourist; I can’t go on a bus/bike/walking tour; I can’t stay in a touristy part of town or eat at a touristy place, picking my meal based off pictures on the menu. I’m the person who lived in Barcelona and never saw the Sagrada Familia. I am the person that lived in Thailand and never took a cooking class– which I’m first to admit, should be a criminal offense.

I am the person that can’t be seen as a tourist. I. Simply. Cannot. Do. It.

However, I am also the person who recognizes that opening oneself up to new things might render something exciting and interesting. So I decided this time I was going to turn every “I can’t” into “Fuck it, yes!” I was going to see and do as much as I could and get as much as I could out of it. I devoured Georgette’s blogs to find links and ideas. I studied her Instagram like I was cramming for an exam.

I booked an Airbnb off a picture of a piazza and went down rabbit holes of other people who had gone to live in Florence and stayed. I started writing to strangers I’d find on social media, shelving my shyness and putting myself out there, literally, in the hopes that someone would respond.

And respond they did. I connected with Coral, a pixie of a lady who started an amazing tour company called The Curious Appetite. Stemming from her own love and obsession with food, wine and Italian culture, Coral wanted to create a place where people visiting Florence could have an authentic experience, rather than a big boring tour of vineyards and churches. She offers a more adventurous approach to tours with day trips to Tuscany, mom and pop vineyards and craftsmen shops. She also has dinner-crawls through the local haunts in Florence and old-timey craft cocktail tours. I immediately signed myself up for the first available tour– the day after I arrived. Might as well bang out the touristy stuff in the beginning, right?

Everything came together magically from the moment I touched ground. My new yes mantra forced me through the barriers I had been trying to climb over for years. Thanks to Coral I had a truly authentic experience in the Tuscan countryside, complete with a homemade lunch at a vineyard I never would have found on my own or on a bigger tour. When we met up to chat she took me to a café in a part of town I never would have wandered into, and we talked for hours over tea and pie about how important it was that people have an authentic experience both when they are traveling and in their own everyday lives.

The evenings were tough at first. The piazza culture is very inviting; everyone gathers in large groups at night to drink and check in before heading off to home or dinner. But it was also very intimidating, as was the language barrier. I speak French and Spanish, and neither of those helped me very much. Finally, a man came up to talk to me. He was older, didn’t speak any English and could not understand why for the last three nights he had seen me there by myself. It was literally unacceptable to him that I remained alone any longer and with that, I became part of a group of friends that took me in without question. I was invited to every dinner, every party, taken on motorbike rides to mountain tops and car rides to oceansides. No one let me eat alone ever. Everyone wanted to show me a hidden treasure. And sometimes I would sneak off in the day to sit in a café and write stories about the people I’d met, or the people I imagined living in the magical places I walked by everyday.

I stayed two weeks longer than planned and by the time I had to leave I had decided I was coming back to stay. By opening myself beyond what I couldn’t do, I allowed myself everything– with seven extra pounds to show for it. I stared “can’t” in the eye and said yes to myself. Armed with a little research and a few lists, I sat back and let the universe be my guide to not just Italy, but life.

By the time you are reading these words, I will have moved and be living in Florence. And it never would have happened had I not made the promise to myself to say FUCK YES to every I CAN’T that came my way… though I may have to learn to say no to that second helping of pasta everyday. Ciao!

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