A 20-Day Art-Forward Journey by Train
We went to Italy for the art.
My husband—an artist—wanted to stand in front of the great works of the Renaissance, to see them not as images in books but as physical objects shaped by hands, tools, faith, ambition, and competition. We did see those masterpieces. But what surprised us was how much more the experience became once architecture, landscapes, and people entered the picture.
This was a 20-day journey across Italy, guided by museums and masterpieces, but shaped just as much by train rides, city streets, shared meals, and unexpected encounters. Art was the goal. Architecture, travel, and daily life made it unforgettable.
Our route took us through Milan, Venice, Florence, Pisa, Assisi, and Rome, each place revealing a distinct relationship with art, architecture, history, and preservation. The city posts in this series explore the art in depth. This overview is about the journey—how we traveled, where we stayed, and what each place gave us beyond museum walls.
Milan: An Unexpected Beginning
We began in Milan for one practical reason: it was the cheapest flight.
Only as we descended did we realize we were landing at Milan Bergamo, surrounded by farmland instead of city skyline. Watching fields stretch beneath the plane, it became clear we weren’t exactly where we thought we were going—which, in hindsight, explained the price.
A quick stop at the airport tourism desk turned confusion into ease. We boarded a bus directly from Bergamo Airport to Milan’s central train station. About an hour later—and roughly $12 each—we arrived in the city center, having already enjoyed an unplanned introduction to the Italian countryside.
Milan exceeded expectations. Modern yet historic, serious about design, and full of architectural contrasts, it felt layered and alive. We stayed in an apartment west of the city center, in a lively neighborhood filled with music, motorcycles, and late nights—easily our loudest stay.
On our first evening, we learned a key Italian lesson: pizza isn’t always called pizza. When we finally realized the flatbread we were eyeing was scrocciarella, the server laughed—and we came back the next night to order it properly.
Venice: Water, Light, and Backpacks Only
From Milan, we traveled by train, watching rolling fields, distant hills, and soft light pass by the windows. These landscapes felt instantly familiar—the same views captured by the masters we had just seen in museums. The art wasn’t imagined. It was observed.
Venice emerged from the water like nowhere else. Defined by canals, bridges, and reflection, it feels architectural and theatrical at once. We stayed in a small bed and breakfast a short walk from San Marco’s Square.
Knowing Venice isn’t suitcase-friendly, we left our larger bag in luggage storage at the train station and navigated the city with backpacks—a decision we appreciated every time we crossed yet another bridge.
In the evenings, Venice surprised us with its warmth. We watched football in a local pub alongside NFL fans from around the world, and nightly dinners turned into easy conversations with neighboring tables. Venice felt social, welcoming, and lived-in.
As a full moon was approaching and the water was rising, we left Venice knowing this would not be our last visit.
Florence: Time to Linger
After Venice, we continued south by train to Florence, where the scenery again explained centuries of artistic obsession—light grazing the countryside in a way that feels almost intentional.
Florence was the heart of our trip and our longest stay. We slowed down here, giving ourselves time to linger in museums, study architecture, and absorb the city that shaped so much of Western art.
We stayed in an Airbnb near the Pitti Palace, which allowed us to settle in. A nearby yoga studio gave me a grounding routine, and visits to the Florence Municipal Market meant we cooked a few meals at home. Florence rewards patience. It asks you to look closely—and gives a lot back.
Assisi: A Gentle Shift
The train ride from Florence to Assisi marked a noticeable shift in both landscape and pace. Rolling hills, olive groves, and quiet towns replaced the dense rhythm of Florence, offering a softer introduction to Umbria. Traveling by train made the transition feel intentional, as if Italy itself was easing us toward something older, slower, and more contemplative.
On this leg of the journey, we met a German woman traveling solo. She had broken away from her tour group, choosing her own path south toward Sicily. Her quiet confidence matched the moment perfectly—an unplanned encounter that reflected the spirit of the journey itself. Italy, especially by train, has a way of placing people briefly in your path, then sending everyone forward again.
Assisi sits above the Umbrian countryside, and from the moment we arrived, its deep religious history was impossible to miss. This is a living pilgrimage town, not a preserved one. Priests and nuns move through the streets as part of daily life. Pilgrims walk with purpose between churches. Bells echo across stone buildings, marking time in a way that feels centuries old rather than scheduled.
Rome: Everything at Once
Our final stop was Rome, where everything converges.
Empire, faith, ambition, architecture, and artistry exist in visible layers built across centuries. We stayed in an Airbnb again, but this time we barely settled in. Rome pulls you outward. We walked endlessly, ate late, and experienced the city both day and night.
Our final day—spent in the Vatican Museums, the Sistine Chapel, and St. Peter’s Basilica—felt like both a culmination and a quiet pause. Standing beneath Michelangelo’s ceiling and inside St. Peter’s vast interior was pure magic.
The Journey wasn't Linear - It was Cumulative
Each city added context to the next. Architecture explained paintings. Landscapes explained color. Train rides explained perspective. The people we met added warmth and humor.
Italian art may have been the reason we came, but the experience of Italy—how it moves, preserves, and lives with its history—made the trip far richer than we imagined.
The posts that follow explore the art city by city.
This was the path that led us there.
Packing & Logistics Sidebar
What Worked (and What We’d Do Again)
✈️ Flights
- Flying into Milan Bergamo can save money—just plan for the bus transfer to Milan Central Station.
🚆 Train Travel
- We traveled by train between all cities after Milan.
- Trains were efficient, comfortable, and scenic—book seats in advance for longer routes.
- Watching the landscape roll by added context to the art we were seeing.
🧳 Luggage
- Pack light. Seriously.
- Venice is not suitcase-friendly—use luggage storage and bring backpacks.
- A small rolling bag + daypack worked best.
🏨 Where We Stayed
- Milan: Apartment in a lively neighborhood west of city center (great energy, loud nights).
- Venice: Bed & Breakfast near St. Mark’s Square (walkable and convenient).
- Florence: Airbnb near Pitti Palace (perfect for longer stays and slower travel).
- Assisi: A small Bed & Breakfast up in the center (walkable and lets you experience the quiet nights)
- Rome: Airbnb, but we barely stayed in—Rome is meant to be experienced outside.
🍝 Food Tip
- Menus vary by region—and by name. Ask questions. Laugh when you’re wrong. Order it again tomorrow.
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