Shockingly, with all of the European travel I’ve done, my experience with Italy is limited to a few days in Venice, and a day each in Rome and Naples. That’s it. Given that I’ve spent months in France, Spain, Portugal, the UK, and Germany, that’s pretty sad. So when it came time to plan my 2023 Europe trip, it was an easy decision to make Italy my “focus” country.

By the time you read this, I will have nearly finished three (hopefully awesome) weeks in Ireland, and will be flying into Rome to start this second leg of my trip. As is my basic preference these days, I’ll be focusing on just a few cities for relatively long periods of time in an effort to both get to know them from the sense of feeling like I live there and to slow the pace of the trip to give me time to write. If I waited until returning to California before writing, I’d have long forgotten what I’d done and which church/palace/museum was which.

The basic itinerary is below. While the places are set, some of the specific things I’ll be doing in each place are, of course, subject to change based on weather and other random things that can come up over the course of a trip.

Day One: Ennis, Ireland to Rome

After a long bus ride to Dublin and a (sadly) RyanAir flight, I’ll arrive in Rome, head to my Airbnb, and crash.

Days Two Through Seventeen: Rome

My basic Rome activities will be split into three categories: Ancient Rome, Catholicism, and other. So I’ll be seeing the Colosseum, Pantheon, and Forum; exploring the Vatican Museums, St. Peter’s (and loads of other churches); and checking out art, pasta, and some aspects of Italian unification and the rise of fascism.

More than that, I’m excited to explore the city, to find my local espresso bar and gelato outlet, to roam Rome (hahaha) and get to know the city while trying not to rush around to see yet another church or museum. I’ll be writing about as much as I can that speaks to me, trying to bring new and refreshing insights into the Eternal City.

Day Eighteen: Rome to Naples

I didn’t like Naples during the one day I had there back in 2010. So I want to give the city another chance.

Days Nineteen and Twenty: Naples

One day is set aside for Pompeii and the other will be spent in the city itself. And both will have pizza.

Day Twenty-One: Naples to Rome

Back to Rome and my apartment!

Days Twenty-Two Through Twenty-Eight: Rome

I’m sure I’ll have left all of my above plans unfinished. So I have another week or so to try to get as many done as possible.

Day Twenty-Nine: Rome to Florence

After four weeks in Rome, it’s off to Florence, a city I’ve never visited that I plan to love.

Days Thirty Through Forty: Florence

My plan for Florence is to explore the Renaissance through the eyes and works of some of the city’s most famous citizens: the Medici, Michelangelo, Leonardo da Vinci, and more. In addition, I’ll likely take a day trip to Pisa. Everyone says it is overrated, but I want to see the darn tower and see if there’s anything else to write about.

Day Forty-One: Florence to San Marino

Two trains will take me to Remini, from there to catch a bus into the micro-nation, the last of Europe’s five such countries for me to see.

Day Forty-Two: San Marino

I have one full day to explore (plus the prior evening), so I’m going to see as much of the tiny country as I can. I want to tell the story of how San Marino maintained independence when the rest of Italy unified around it. I love history!

Day Forty-Three: San Marino to Florence

Back to Florence, a bus and two trains away.

Days Forty-Four Through Fifty-Four: Florence

More to see, more to eat, and a side trip to Siena, where one of my closest friends lived for a while in college.

Day Fifty-Five: Florence to Milan

One more city change in Italy, up to the most modern city in the country.

Days Fifty-Six Through Sixty-Three: Milan

Obviously I want to see the Duomo, but I also want to experience La Scala and maybe the fashion industry in some tangential way to be determined. I must admit I’m not terribly excited about Milan, but I do hope to be pleasantly surprised.

Day Sixty-Four: Milan to Copenhagen

Off to part three of my trip after two and a bit amazing months in Italy!

So that’s the itinerary. While stories will be delayed (after all, Ireland articles haven’t even started yet), you can follow my Instagram for daily photos. Those will happen roughly in real time.

Below is a map of this portion of the trip. Rome is in blue, Naples in orange, Florence in yellow, San Marino in green, and Milan in red.

2 thoughts on “Trip Itinerary: Italy

  1. Jonathan,
    While visiting Napoli (which I also didn’t like on my one morning there), don’t miss nearby Sorrento (which I LOVED on that same afternoon)!

    1. Sadly I won’t have time to get down to Sorrento. The downside to the way I travel now with huge chunks of time in few places is the inability to see all the places I want to see.

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