My boyfriend and I excitedly joined his parents and a lively group from Conquering Cuisine for a guided tour through Italy. Before the trip, we wrapped up as many projects as possible ā but being the responsible (read: slightly neurotic) professionals we are, we still packed our laptops.
We did do a little work at first⦠until the rolling hills of Tuscany and Umbria convinced us otherwise. The further we got into the trip, the less we opened those laptops ā and honestly, it was pure bliss.
The last time I toured Italy was thirteen years ago with my grad school alumni group from Gannon University in Erie, Pennsylvania. That trip gave me lifelong friendships, memories that still make me laugh-snort, and probably a few pounds that Iāve never lost. I had a feeling history would repeat itself ā and it did. New friends, same laughter, and more pasta than any waistband could handle.
So, in the spirit of āwhen in Romeā (or Florence, or Siena, or Pienzaā¦), here are a few fun lessons I learned on this Italian adventure.
š Embrace the Expanding Waistline
This is not a trip for skinny jeans. I strategically wore dresses for two reasons:

- Layering (October mornings can be in the 50s, afternoons in the 70s).
- Freedom.
Italy is a country that wants you to eat ā deeply, passionately, unapologetically. You canāt possibly say no to pasta made with love, truffle everything, and wine that deserves its own love song.
So, I set my belly free. Be free, belly, be free!
š· Quality Over Quantity
One of the most refreshing differences in Italy is how much people value quality over quantity. Each small producer we met was wildly passionate about making something good, not making a ton of it.
Thereās a calm rhythm to their days ā or maybe I just didnāt notice any chaos because I was three glasses deep into a bottle of Brunello di Montalcino. Also, Italians eat dinner late. As in, āIām already in my pajamas and youāre just opening the Chiantiā late. So, to all my fellow travelers I Irish-goodbyed mid-happy-hour: it wasnāt you. It was me⦠fading gently into the night like the last note of a slow love song.
šæ When in Rome⦠Try the Bidet
Listen. Donāt knock it till you try it.
The Europeans are onto something here ā and I bet they didnāt panic-buy toilet paper in 2020.
Thatās all Iām saying.
š Comfy Shoes Are Sexy (Yes, I Said It)
Italy is built on hills and cobblestones that are beautiful but brutal. I wore Skechers on a 20 mile walk in Spain and I remember how much they rocked. However, I wasn’t going to wear Skechers slip-ins ā I mean, Martha Stewart shoes? Really? I’m just not a Martha fan.
Well. I was wrong.
As a runner with foot pain, I slipped a pair on and became a renewed Skechers fan. (Okay fine, I brought three pairs.) The Italians wear them too ā and if they can make Skechers look cool, so can we.
Pro tip: hotel rooms in many Italian cities are tiny. I got really good at stuffing my socks and underwear inside my shoes. Space-saving and mildly embarrassing. Win-win.
š Milestone Moments Are Expensive Everywhere
From chatting with our charming bus driver and tour manager, I learned that Italian couples ā much like Americans ā are waiting longer to get married, have children or buy homes. Weddings and real estate are pricey, even under the Tuscan sun.
Both guys had been dating their girlfriends for more than seven years. Iād say thatās long enough to learn if someone snores or steals all the covers.
š¶ Dogs (and Their Fashion Choices)
In Italy, dogs donāt wear clothes, but they do have fancy collars.
The truffle-hunting dogs we met in the countryside were rugged, happy, and definitely not wearing sweaters. We met Wolfie, who may have been a Great Pyrenees, who was the alpha. His job was to keep wolves away from the sheep. He wore a collar spiked with nails so nothing could clamp down on his neck during a territory scuffle.


My Florida dog, however, owns dresses ā plural. Yes, I have become that person. I used to roll my eyes at people who pushed dogs in strollers. Now? I nod at them in solidarity. I feel like it might be time for my dog to get a job, even if it would be visiting nursing home. Get to work Penelope!
š®š¹ The Language of Beauty (and Wine)
Most Italians we met spoke gorgeous, articulate English ā thoughtful and precise. I was inspired to speak better English, honestly.
I told myself Iād memorize more Italian phrases. Every day Iād think, āTonight Iāll study.ā And then Iād drink the wine. And⦠well, you can guess how that went.
⨠Final Thoughts
If you want a trip that fills your heart, expands your waistline, and makes you rethink your shoe choices ā Italy is the place for you.
Go with an open heart, a stretchy dress, and a sense of humor. Because between the rolling vineyards, charming locals, and accidental bidet experiences, youāll find what travel is really about: connection, laughter, and living a little more freely.
āļø Have you been to Italy?
What was your favorite memory (or biggest travel fail)? Drop it in the comments ā Iād love to hear your story.
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