To me, the magic of Italy is the layers - and I don’t just mean the lasagna.

At the base you’ve got Caesar, Sulla, and the glory of Rome. Drizzle on the middle ages with Pope, the Vatican, and the whole “center of Medieval Europe” thing. Toss on Michelangelo and Renaissance Florence and for the final topping, add the expressive people and sun-kissed arches that make up modern Italia.

What Makes Italy Unique

Italy wasn’t just the center of the world. Italy was the center of the world multiple times for multiple reasons. What takes your breath in Italy is the stratified symphony of interconnected layers. It’s empire, worship, and art, all telling the story of us.

My Italy Trip

Much ink has been spilt on this iconic destination, so let’s bring this post back down to earth. Here’s a personal take on my first big trip to Italy.

5 Places | 4 Foods | 3 Thoughts | 2 Keys | 1 Celebration

5 Places

Florence: Beautiful and world-changing. But in 2023 the most over-touristed place I’ve ever been. Let the Duomo and the Uffizi stun you - and then get out as fast as you can!

Tuscany and Umbria: Ancient hilltop cities sprinkled over lush, vineyard-filled valleys. The quiet beauty in the upper hills of Cortona is a spiritual experience - that you will need after bustling Florence :)

The Amalfi Coast: What’s makes a beautiful landscape? Mountains? Or sea? How about both. Might as well make it an endlessly tall cliff jutting out over the Mediterranean. Stack charming, ancient fishing villages one on top of another until they disappear into the clouds and BAM! You’ve got the Amalfi Coast.

Must-do: Path of the Gods and a sunset boat ride.

Rome: Fight the crowds to see the iconic sites- or if you’re like me, just watch Fall quietly creep in from the banks of the Tiber. St. Peter’s and the Pantheon are the must-sees. Everything else makes for a great “bike-by”.

Bologna: Go for the food and the arched sidewalks! … And did I mention the FOOD?

About that…

4 Foods

I ate all the carbs in Italy. Sue me. Here’s a few food highlights:

Olive Oil: Between mafia exports and no US regulation, the olio d'oliva we get in the states is very hit-or-miss (deep dive here). Olive oil in Italy is a wonder for the tastebuds and a miracle for your health!
Gelato: Most gelato is a 2x improvement on ice cream. But the shop by the two towers in Bologna? Nirvana.
Aperol Spritz: Aperol, prosecco, club soda, slice of fresh orange. One innkeepers secret: tonic water instead of club soda.
Pasta! Handcrafted, with 10x more variety than I knew existed. Must do: Ragu and Carbonara

In Italy, it’s the beauty in the little things. But the little things may just give you space to think about some bigger things…

3 Thoughts on Travel

Travel in 2023 is the best bang for your buck on the planet.

Let’s face it, America: housing, college, medical bills- most big things are wildly more expensive for millenials than they were for our parents.

The one thing that’s cheaper and smoother than ever before: seeing the world. Between miles, apps, and the advent of a little thing called “AirBnB”, travel is one thing we can do today with an ease that would blow the minds of our predecessors.

Anyone can travel- which brought me to my next realization.

Travel has been Democratized (for better and worse)

Upside: In 2023, everyone can go to Italy!
Downside: In 2023, everyone can go to Italy :/.

With travel becoming easier and cheaper, seeing popular sites, especially during peak season, is becoming a recipe for misery. The new key going forward? Finding the hidden gems.

And even when you nail it, travel only goes so far in life.

The Diminishing Returns of Travel

There is a diminishing return to getting away.

To be clear, I believe in travel. Travel and books are powerful ways to get outside of our “normal” routine… and more importantly, our “normal” assumptions about life.

But going is not an end in and of itself. As an idol, travel will leave you unfulfilled.

Time away serves its purpose to the degree that it re-awakens you to the meat and potatoes of a good life: spirituality, relationships, and meaningful work.

2 Keys to Avoid Misery

I’ll shoot straight with you. The iconic Italian spots were the most touristy places I’ve been to in my whole life. Once you’ve identified what you want to see in this sought-after country, the key in trip-planning is to solve for crowd-avoidance.

To do that:

NEVER GO TO ITALY IN PEAK-SEASON: A trip to Italy in the summer is a sure-fire way to spend two weeks on a hot, crowded bus being shuffled off to hot, crowded lines. We went in early October… I might go even later.
Biking is a Superpower: No exaggeration- biking saved our trips to Florence and Rome. Bypass the the packed subways and overflowing sidewalks, stay in a quiet spot, and see more in a day by bike than you can see in a week on foot.

And finally, it was a ten-year anniversary that brought us to the boot of Europe in the first place.

1 Decade of Marriage

They said marriage would be tough. Three kids, ten years, and a whole lot of life later, I see what they meant. But even if it ain’t always easy, it’s always good. In a world that increasingly pushes us towards atomization and dissolution, marriage is one of our last remaining tethers to connection, to family, and to unconditional love. And that’s worth strengthening - and celebrating.

It’s been an awesome 10 years- here’s to the next 10. Andiamo!

Traveling Italy