Living the Journey: Exploring Travel, Culture, and Connection Through an Expat’s Eyes

​The Winter Olympics have a special way of bringing the world together, creating moments that mix competition, culture, and connection. With the 25th Milano-Cortina Games in full swing, I find myself caught between excitement as a travel advisor, an expat, and a fan.

If you missed last week’s post where I shared my adventures from Munich to London—blending work and play—you can catch up here: From Munich to London: Work and Play Combined.

The Wandering Puffin welcomes the world to Milano – Cortina. Well, maybe not officially, but today I have clients arriving from Missouri—two sisters coming to Milan to enjoy the 25th Winter Olympics. So in a way, yes, I am part of the excitement, and given how international this past week has felt, it’s fitting.

---

Interestingly, while living here, I had chances to find tickets to an event or two (Milan is less than 4 hours by train from Rome), but it never really crossed my mind to go. The games are in full swing, and Rosa and I watched a streamed version of the opening ceremony from the comfort of our home last week. I’ve streamed events here and there between working on travel plans for clients, teaching English, and simply living life. I’ve found myself caught up in the Olympic drama—perhaps as an escape from the chaos happening across the pond. I even teared up a bit when the US skating team received their gold medal and the national anthem played.

​Have you ever found yourself cheering for two teams at once—whether in sports or in life? What was that like for you?

It’s a strange place to be as an expat—still rooting for the home team but now having a new home team, too. I wished my wife luck for the Italian women’s hockey team as they moved into the quarterfinals against the US. I wonder if she and I will develop some fun rivalries moving forward. Yes, Italy is home now, and that’s not changing anytime soon, but friendly sports rivalries add some spice—and make each of us better.

Last week truly had an international flavor throughout. Usually, as the new blog has evolved, the focus is business-oriented, and yes, I do have clients coming here over the next few months, including the sisters attending the Olympics. But I guess it’s okay to add personal touches here and there.

This past weekend, Rosa and I went out to an Indian restaurant and then attended a comedy show at Teatro Trastevere here in Rome. The comedian, Nya, is an African-American with Liberian roots from Brooklyn, New York, now an expat in Berlin for about two years.

The audience was a mix of expats from America, Canada, Australia, New Zealand, India, Denmark—and even Italians. The show, called American-ish, was in English and was very funny and interactive. As the name suggests, it touched on being the new kid in a new land and trying to find your place. After more than a year and a half in this new life, I guess I’m pretty much American-ish myself. Yet as I mentioned, I’m still rooting for the “home” team on many fronts—not just sports, but life. That perspective, at this moment in time, definitely impacts my business, so I’m mindful to protect it.

How do you blend different cultures in your life or travels? Are you ‘American-ish’ or something else?

Nya had never been to Italy and had heard about the “rules” I often share with clients about eating habits and regional cuisines. The Italians and other expats were happy to share the unspoken rules, but his monologue about the almighty bidet really stood out. Did you know the bidet was actually a French invention? But chances are if you stay in a hotel in France, you won’t find one—while Italians are truly in love with it. Rosa and I have one in our bagno as well. (And yes, I’d love to hear if you’ve ever encountered a bidet moment while traveling!)

Keeping with the international theme, I’ve heard the Japanese have improved the original bidet design, and during and after the pandemic, Americans, facing toilet paper shortages, started installing them too—probably only those who could afford it or who wanted to show off their modern tendencies. Whether the bidet fascination faded after shelves at Walmart, Target, or Costco refilled, I don’t know.

What’s the quirkiest or most surprising cultural tip you’ve learned while traveling?

---

The show was excellent, and if Nya comes around again, I’d happily see his performance once more.

At the end of the night, during the meet-and-greet, I thought about this identity of mine: I’m an expat, yes, but also an immigrant because moving back to America isn’t in the cards anytime soon. An expat is someone who might consider returning home; an immigrant is someone who plans to stay. As a permanent resident, I emigrated from the US to Italy. No positive or negative connotation—just a fact.

So, that was last week—normal as usual except for the small event of trying to watch the Seattle Seahawks and New England Patriots game after we got home, despite a 9-hour time difference. I caught the first half before falling asleep, and Rosa just said, “Buona notte.”

Where have your travels or life experiences made you feel most at home—and why? I’d love to hear your stories!

Navigating new cultures and experiences—whether at an international event like the Olympics or through everyday moments like a comedy show—is what makes travel, and life as an expat, so rich and rewarding. If you’re dreaming of your own adventure abroad, whether it’s exploring Italy during a world-class event or uncovering hidden gems off the beaten path, Wandering Puffin is here to help you plan every step with expert care and a personal touch. Because with us, travel isn’t just a trip — it’s an adventure, and we want you to truly experience it!