Two Week Winter Itinerary in Italy (Rome, Cinque Terre, Florence, Bologna)

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During the winter holiday, we spent 14 days in Italy! Dan and I were married in 2022 and saved up money to go on our belated-honeymoon. We also joined up with family during the second week of our trip. Our last European trip had minimal downtime between planes, trains, and countries (to read what I’m talking about, you can find the itinerary here), so we decided to slow down and focus on a couple spots this trip for longer durations. I will definitely say that you gain an appreciation and understanding if you are somewhere longer than a night or two. It’s like going back to your favorite beach (or mountain, hiking, biking, etc.) spot again and again.

The following is the shortened version of our itinerary:

Days 1-4: Rome

Day 0 was actually a travel day, since it took us a full day to get to Rome. Day 1 was us mostly sitting at the airport in Paris (amazing sandwiches- no complaints) and landing around 7 PM in Rome. After a train ride, we ended up in Trastevere, a local neighborhood. We opted for Airbnbs during this trip and found a quaint loft tucked away in an apartment building. Our neighborhood was one of the best parts of the experience. It was within 20 minutes walking distance of the main sites: Vatican City, the Colosseum, and the city center.

Screenshot from Google Maps

Day 2 was spent visiting the Vatican Museums, including the Sistine Chapel. We booked a guided tour through the museum. I would go back to Rome to just visit the museums again. After our tour, we walked over to the city center and visited the Trevi Fountain. We spent most of our afternoons/evenings in Trastevere.

Day 3 was spent touring the Colosseum, including the underground, the Roman Forum, and Palatine Hill.

Day 4 was an open day, so we decided to wander and see what we haven’t seen yet. We went back to Vatican City and waited in line to go into St. Peter’s Basilica. Later that day, we went into the Pantheon.

It’s been four months and I am still dreaming of Rome, the food, the architecture. Even if you just wandered the city, there’s so much to see. You can read the Rome itinerary more in depth in this blog post.

Remains of the arena in the Colosseum

Days 5 & 6: Cinque Terre

Around mid-morning, we hopped on a train and traveled four hours following the coast to Riomaggiore, the first Cinque Terre village you will encounter if you are visiting from the south. After many, many, many steps to our apartment, we enjoyed the quiet sunset and walked to get dinner at the only place open. In the winter, there are barely any tourists, so the shop options are limited.

This trip was about capitalizing our time, so we researched a few of the towns and chose two we wanted to visit. Without a car, you can get to the towns by train or by walking the footpath that connects them. We wanted to do both. Since the trains only run every hour in the off season (every 15-20 minutes in the on season), we didn’t want to go to every town and lose any experience. Our first stop was Vernazza, where we visited the harbor, but everything was closed, so we hopped on the next train to Manarola. Manarola had more shops open, the sun was out, and the people were friendly. We had coffee at Cappun Magru, focaccia and wine at Nessun Dorma, and shopped for souvenirs. To get back to Riomaggiore, we walked the footpath Manarola – Riomaggiore (Via Beccara).

Riomaggiore had a different vibe in the day time, a couple more places were open, including a small wine bar- Ghemé. We enjoyed the sun and made our way back to our Airbnb before the sunset.

Day 7: Day trip to Pontremoli

Pontremoli is a small city in northern Tuscany (yes, you read that correctly- away from the main travel destinations you’ve heard about) approximately an hour and a half train ride from Riomaggiore. Why did we go there? Great question! My husband’s great-grandfather is from there. It also gave us an opportunity to explore a place off the beaten path (to us).

When we got there, we didn’t know what to expect. We thought it would be us walking through a town and getting back on the train. As the day wore on, the town came out. Everyone was doing their Saturday shopping and visiting friends. All of the cafés were packed with people, a farmer’s market was going on in the middle of town, where people were buying their meats and cheeses. We were looking up at a medieval castle and cobble stone walkways like we were extras in Game of Thrones. The place was surreal.

Some places we visited were Piagnaro Castle, the museum inside the castle, Chiesa di San Geminiano, and La Caverna dei Nani for a beer. In the early afternoon, we hopped back on the train toward Florence, roughly a four-hour ride from there.

When we got to Florence, a place we’ve been previously, the familiar surroundings came back to us as we made our way to the Piazza di Santa Croce area where our Airbnb was located. Our family was already waiting for us to go explore and go out to dinner. This was our second time in Florence around Christmas and I will say, the decorations themselves are amazing.

Pontremoli from the Piagnaro Castle

Days 8-15*: Florence

For the next week, we walked around quite a bit along the river, went into the Basilica di Santa Croce, awed at the David at the Accademia Gallery of Florence, wandered the Piazza della Signoria, scoped out the Piazzale Michelangelo, took a guided bus tour into the Chianti hills where we visited two wineries- Tenuta Riseccoli and Poggio Amorelli, and attended a ACF Fiorentina match VS Torino.

Ponte Vecchio in Florence

Day 12*: Day trip to Bologna

Early morning on Day 12, we took a high speed train (35 minutes away) to Bologna. Bologna exceeded our expectations- the people, architecture, and food were more diverse than we realized going in. The city was busy with people, but the vibe was more “these people live here” versus “we are all on vacation.” For a bigger city, it wasn’t as busy. We spent the day wandering in the sunshine, taking pictures in the Piazza Maggiore and Piazza Santo Stefano, visiting the Basilica di San Petronio, and our favorite stumble upon, finding the “foodie street of Bologna”- Via Pescherie Vecchie and Mercato di Mezzo. And let’s not forget seeing the Two Towers!

Piazza Santo Stefano in Bologna

Kicking off the New Year!

The last thing I will say is New Years Eve in Florence was an experience- each of the piazzas had their own theme with different styles of music playing at each one. These are free experiences that you can take in. We watched a concert orchestra play on the steps of Basilica di Santa Croce, since it was closest to our place of stay.

I love Italy and cannot wait to go back, but our travels might be taking us to new places!

~**~**~**~**~**~**~**~**~**~**~**~

If you could travel anywhere, where would you go next?

5 responses to “Two Week Winter Itinerary in Italy (Rome, Cinque Terre, Florence, Bologna)”

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