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A Diary of a Trip to Italy—from Fifteen Years Ago

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My one-and-only trip to Italy was fifteen years ago, with one of my best friends, Erin.

Myself (left) with Erin (right)
Myself (left) with Erin (right)

It was a three-week immersive art history course through her college. The first week was spent in the classroom, learning very basic Italian and some historical background about the artwork we’d be seeing. Weeks two and three were spent in Florence, Siena, and a handful of smaller towns throughout Tuscany. I skipped Week One (to focus on my own studies at my university—honest!) and joined for the fun part—the travel.


I kept a journal of the whole trip, and despite my devotion to Marie Kondo, I didn't throw it away. And not only did I keep it, but I'm also publicly sharing pages from it, as I write commentary on the entries to my younger self:

Dear Lindsay,

Hi! It’s future you, writing from the year 2016. Don’t freak out.


You know how Oprah has said she’d put in her will that all of her journals be destroyed upon her death? Maybe she hasn't said it yet. Either way: That might be a smart move. Moving forward, let’s consider implementing a Destroy-Every-Decade rule. Just think about it.

Writing down all of your grades for posterity, huh? Well, the good news is, you will make it through both undergrad and graduate school with grade points high enough to make your Type A, people-pleasing self happy.

The bad news is that it will take you some time to be able to shake the belief that everything you do needs to be perfect. (In truth, you're still working on it.) Nine years from now, you will cry real tears over gluey, lumpy mashed potatoes. But fifteen years from now, you will laugh about bitter artichoke soup and a Pinterest-egg-dyeing project gone wrong. Growth takes time, be gentle with yourself.

Oof. We could start a drinking game with the number of times you say “so” in here. So big! So beautiful! Not that I don’t have writing crutches: Even now I’m consistently overusing a few words—I guess I’m saying thank you for the reminder to work on that. Also, you know how Greg continues to suggest getting a degree in English? Speaking from experience, it might be worth considering…

I vividly remember the flavors of these mint-flavored Skittles and the licorice ones you got, too. Good choice. Skittles are one of the few chewy candies that you still indulge in occasionally, because you become a vegetarian, and they are gelatin-free.

That “good luck hog” is a boar by the name of Porcellino, and unfortunately, you haven’t made it back to Florence yet. But, the good news is that the discovery of this diary has prompted a discussion with Erin to finally figure out our return trip—thanks for ensuring it with those well-placed coin falls.

Oh, and a cappuccino every morning? Why did I ever drop that habit?!

Ooh the pasta at Lo Scudo. That “ravioli with spinach and cheese w/ a mushroom sauce”? You’ll go back to the restaurant two more times to get it again. For what it’s worth, you don’t change much in this respect: You’re always up for trying new foods and new restaurants, but when you find something you dearly love, you stick with it.

Did you throw out clothing? I can’t imagine how you fit all of this in your suitcase?! I know you brought back a ceramic bowl, plate, six wine glasses, and at least two bottles of wine, maybe more.

It’s easy to see why Siena was one of your favorite cities, not only it is a beautiful place, but you felt truly immersed thanks to connections with the people. You certainly enjoyed eating dinner with several young members of the Contrada della Lupa (you’re welcome for sparing you the embarrassment of sharing that page), but more so, you enjoyed talking with Leonardo. (I think you thought of him as one of the wise elders of the contrada, we’ll set aside the fact that he was probably only middle-aged.)

Remember that feeling. Experiences become infinitely more meaningful when you’ve made a connection with someone else.

Another important lesson to hang on to: often a photograph really can’t capture the beauty of a moment. And beautiful views trump groooossss hotel rooms every time.

I told you you’d make it back to Lo Scudo multiple more times. And see, that “feeling like a regular” part, it’s because you made friends with one of the waitresses. Like I said, it’s all about the connections. And in other good news—Mike still has the power to make you smile so wide your face hurts.

Until we meet again,



(Yes, you are Lindsay-Jean now. It has to do with getting married, not wanting to get rid of any of your names, and a cranky worker at the Secretary of State’s Office when you went to change your license.)

Tags: italy, journal, diary