The Anthony in Italy Podcast

Nate and I sat down for one of those meandering, no-rush conversations about what it’s actually like to live in Italy—not the Instagram version, but the messy, funny, frustrating, sometimes absurd day-to-day stuff. We talked about learning Italian (and butchering it along the way), the oddities of dining out, what it means to be a musician here, and how different the cultural wiring is compared to the U.S. There’s beer. There’s music. There are stories about language mishaps, the real cost of living

Talking taxes in Italy is no picnic — especially if you're a foreigner trying to navigate the system. I sat down with Giovanni Cervini to dig into some of the stuff that trips people up the most: tax residency rules, what happens if you own property, double taxation headaches, remote work implications, and how all of it changes if you’re new to Italy. Giovanni laid out how the Italian system looks at fiscal residency (hint: it’s not just about where you sleep), how remote workers should plan

In this episode, Erica gets real about what it’s like to pack up your life, move your family across the ocean, and start over in Italy. We dig into why they did it, the hoops they had to jump through for citizenship, and what it’s actually like navigating daily life, schools, and cultural differences with kids in a brand new country. Erica doesn’t sugarcoat the challenges, but also shares how rewarding it can be raising kids in a place where life moves differently. If you’ve ever dreamed about

In this episode, I sit down with my friend Andreas to talk about what it’s actually like building a life—and a business—in Italy. We get into everything from cultural identity and language learning to the weird realities of Italian bureaucracy and what it takes to thrive here as a foreigner. We also dive into the cocktail scene, community-building, and how Italy’s approach to food, service, and even music (yes, metalheads exist here too) reveals a lot about the culture. It’s part travel story, part

In this episode, I talk with my friend and business partner, attorney Christina Prejean, about what it really takes to get Italian citizenship. Christina shares how her background—including time in the military and a serious travel bug—led her to dive into dual citizenship. We get into the nuts and bolts of the process, why an Italian passport is worth chasing, and how getting help from someone who actually knows what they’re doing can save you a ton of time and headaches. If you’re curious about

In this episode, I talk with Giulia Speziali—an Italian language teacher from Perugia—about everything from her time teaching in China to what makes Italian such a weirdly emotional language to learn and teach. We get into how people actually learn languages (hint: it’s not from grammar books), how TikTok is changing education, and why pronunciation trips people up more than anything. We also unpack Italian culture from both inside and outside—how Italians act abroad, what coffee means here, and why

In this episode, I talk with Sonya about what it’s really like to move from Russia to Italy. We cover everything from language struggles to cultural curveballs—plus what surprised her most about Italians. We also dig into what it feels like to be an expat, the weird differences between life in the US and Italy, and how travel restrictions have shaped our lives in unexpected ways. Sonya shares some solid advice for Russians thinking about traveling or moving to Italy, and we both reflect on the weird

In this episode, I sit down with my friend Cosimo Serpolla to talk honestly about life in Italy—what works, what doesn’t, and what people don’t tell you before moving here. We dig into cultural expectations, job market frustrations, how the experience differs if you’re LGBTQ+ or an expat, and why cities like Brussels keep pulling people away. If you’ve ever dreamed of living in Italy, this one’s for you—just don’t expect a sugar-coated fantasy. We’re talking about the real deal.