Earlier this year, my husband and I embarked on an unforgettable winter getaway to Italy for just under two weeks, and it was truly a dream come true! Traveling during the winter season allowed us to experience Italy in a more peaceful and intimate way, away from the usual crowds. We were able to enjoy Italy’s stunning winter landscapes, delicious seasonal food, and rich culture at a slower pace.
As first-time visitors, we spent weeks researching everything—where to go, how long to stay, and the best winter activities to enjoy. We were determined to make the most of this magical winter trip!
In this post, I’m excited to share a general overview of our entire two-week winter itinerary, including the best places to stay, eat, and what to do each day. I’ll also be sharing detailed itineraries for each destination in the coming weeks, but I hope this overview will be helpful for those planning their own winter travel adventures in Italy!
Days 1-3 – Rome
We arrived in Rome on Day 1 of our Italy winter adventure and spent 3 action-packed days exploring this vibrant, historic city. Despite Rome’s size and fast pace, we covered over 10 miles of walking each day, indulging in authentic Italian cuisine and immersing ourselves in world-renowned historical landmarks.
Though Timothy and I typically prefer quieter destinations, our 3 days in Rome were the perfect amount of time to see all the must-visit sights before moving on to our next destination.
Here’s a list of everything we explored in Rome in 3 days:
Pantheon: The Pantheon, one of Rome’s most impressive ancient monuments, showcases stunning architecture and serves as a testament to Roman engineering, attracting visitors from around the world.
Colosseum: The Colosseum, a symbol of ancient Rome’s grandeur, offers a glimpse into the gladiatorial games and epic battles that once took place in this iconic amphitheater.
Trevi Fountain: The Trevi Fountain, Rome’s most famous baroque masterpiece, is a must-see both during the day when it glistens in the sunlight and at night when it’s beautifully illuminated.
Roman Forum: The Roman Forum is a sprawling archaeological site that was once the center of public life in ancient Rome, showcasing ruins of temples, government buildings, and more.
Palatine Hill: Palatine Hill offers panoramic views of Rome and is home to the remains of imperial palaces, making it one of the most important ancient sites in the city.
Vatican City and St. Peter’s Basilica: Vatican City, the smallest country in the world, is home to St. Peter’s Basilica, where visitors can admire Michelangelo’s famous Sistine Chapel ceiling and the grandeur of St. Peter’s Square.
Vatican Museums: The Vatican Museums house an incredible collection of art and historical artifacts, including masterpieces by Raphael, Michelangelo, and many others, drawing art enthusiasts from all over.
Piazza Navona: Piazza Navona, a beautiful baroque square, is home to stunning fountains, vibrant street artists, and a lively atmosphere, making it one of Rome’s most charming public spaces.
Campo de’ Fiori: Campo de’ Fiori is a bustling outdoor market by day and a lively nightlife spot by night, offering a mix of fresh produce, flowers, and delicious food in a historic square.
Aventine Keyhole and Parco Savello: The Aventine Keyhole, located in the peaceful Parco Savello, offers a unique view of St. Peter’s Basilica framed perfectly through a keyhole, making it a hidden gem in Rome.
Circus Maximus: Circus Maximus, an ancient chariot racing stadium, once hosted grand spectacles and now serves as a sprawling public park where visitors can imagine the grandeur of ancient Roman events.
Trastevere Neighborhood: Trastevere is one of Rome’s most charming neighborhoods, known for its narrow streets, vibrant nightlife, and authentic Roman restaurants.
Villa Borghese Gardens: Villa Borghese Gardens, one of Rome’s largest public parks, offers a serene escape from the city hustle, with beautiful pathways, lakes, and the famous Borghese Gallery full of art treasures.
Our AirBnB was located in the neighborhood of Monti – about a 10 minute walk from the Roma Termini station. It was the perfect location! So many yummy restaurants and very central to everything there is to see!
Here’s a link to the AirBnB we stayed at:
Whew! Like I said, we did a loooot in 3 days. By the end of that 3 days, we were ready to head out to the countryside. Luckily for us, we were only a 3 hour train ride away from the Amalfi coast!
Days 4-6 – Amalfi Coast/Positano/Sorrento/Pompeii
Just a short 3-hour train ride from Rome, the stunning Amalfi Coast beckons travelers with its rugged cliffs, charming coastal villages, and crystal-clear waters. This picturesque region has surged in popularity over recent years, drawing visitors to its iconic beaches and idyllic towns, especially during the summer months.
Even in the offseason, Positano, one of the Amalfi Coast’s most famous and Instagram-worthy destinations, can be pricey. So, we opted to stay in the nearby town of Sorrento, where we found an unforgettable AirBnB. Nestled on a working lemon and orange farm, our spacious apartment offered breathtaking views of Mt. Vesuvius and the Bay of Naples. It was an absolute dream, and we couldn’t get enough of sipping fresh orange juice while soaking in the scenery. We spent three nights here and could have easily stayed longer to explore more of this enchanting coastline.
Here’s the link to the AirBnB that we stayed in:
We decided to take this portion of our trip a little bit slower. I insisted that we still get up early, but we weren’t rushing from place to place like we were in Rome.
We dedicated an entire day to exploring the Amalfi Coast, and to our surprise, we had Positano virtually to ourselves for a few hours—an experience that’s nearly impossible in the busy summer months! The Amalfi Coast truly lives up to its reputation, with its stunning views, colorful buildings, and breathtaking cliffs. I’d love to return in late spring when the weather is warmer, but the crowds are still smaller, and more attractions are open. It’s the perfect time to experience this beautiful coastal gem without the peak season rush!
We hiked some of the Path of the Gods, which I would totally recommend. So many breathtaking views!
Then we drove all the way down to the town of Amalfi, explored Fiordo di Furore, and just soaked in the beauty of it all.
We did brave driving the Amalfi Coast in a car, but only because we went in the offseason. It wasn’t stressful because there just weren’t very many people at all! But I can’t even imagine trying to drive on the narrow winding road during tourist season when there are a million tour buses trying to also make the trip!
We spent another day in Pompeii, which was insanely cool! So much history and perfectly preserved artifacts. Did you know that they’ve only excavated about 75% of Pompeii?! The other 25% is still buried! How cool is that?!
We also spent a brief time in Naples, for one thing and one thing only, the best pizza in Italy! We visited Antica Pizzeria da Michele, supposedly the very first pizza joint in Italy, and also where they filmed a scene from the movie Eat, Pray, Love with Julia Roberts. I was so stoked to try this pizza, and let me tell you, it lived up to the hype! Definitely worth the trip if you have time!
Days 7 – 9 – Florence
We spent the next three days exploring Florence, and it offered a completely different experience from Rome. Florence is a smaller, more walkable city, allowing us to easily explore on foot. We also found the locals to be incredibly warm and welcoming, a refreshing change from the pace of Rome.
During our stay, we had the pleasure of experiencing two fantastic hotels: Hotel Calimala and Hotel Milu, both situated in different areas of the city. While both offered excellent amenities and service, our favorite by far was Hotel Calimala. This charming hotel boasts a prime location in the heart of Florence, with a rooftop bar offering delicious food and unbeatable panoramic views of the city’s iconic skyline, making it a perfect spot to relax and take in the beauty of Florence.
Here’s a link to learn more about staying at Hotel Calimala:
https://www.hotelcalimala.com/
While we were in Florence, we found our absolute favorite gelato of the entire trip. Venchi. Oh my goodness it was amazing. They have house made gelato and their own version of Nutella that they put in the bottom of the cones, and it is decadent and amazing. I’m pretty sure that Venchi has a chain of stores all throughout Italy, and I would highly highly recommend visiting one of their stores if you can during your trip!
During our time in Florence we visited:
- Duomo: The Duomo, also known as the Cathedral of Santa Maria del Fiore, is Florence’s iconic landmark, offering stunning architecture and panoramic views from its famous dome.
- Uffizi Gallery: The Uffizi Gallery is one of the world’s most renowned art museums, housing masterpieces by Botticelli, Michelangelo, and Leonardo da Vinci in the heart of Florence.
- Pitti Palace: Pitti Palace, a grand Renaissance palace, is home to art collections, royal apartments, and stunning architecture, making it a must-see attraction in Florence.
- Boboli Gardens: The Boboli Gardens offer a serene escape with beautifully landscaped greenery, sculptures, and fountains, providing one of the most scenic spots in Florence.
- Palazzo Vecchio: Palazzo Vecchio, Florence’s historic town hall, showcases impressive Renaissance architecture, art, and stunning views of the city from its tower.
- Giotto’s Bell Tower: Giotto’s Bell Tower, located next to the Duomo, offers breathtaking views of Florence and showcases intricate Gothic design and stunning sculptures.
- Piazza della Signoria: Piazza della Signoria is Florence’s vibrant central square, surrounded by historic buildings and open-air sculptures, including the replica of Michelangelo’s David.
- Ponte Vecchio: The Ponte Vecchio, a famous medieval bridge in Florence, is lined with charming shops and offers picturesque views of the Arno River.
We really loved the food in Florence, very hearty, and everyone was so friendly!
Day 10 – Pisa
We took a scenic one-hour train ride from Florence to Pisa for a day trip, and it was totally worth it! The iconic Leaning Tower of Pisa is even more impressive in person, with its tilt creating a unique and fascinating sight.
After marveling at the tower, we spent the rest of the afternoon wandering through Pisa’s charming back streets, discovering cozy cafes, delicious local cuisine, and hidden gems. If you have time in your Italy itinerary, I highly recommend spending at least an afternoon in Pisa—it’s the perfect spot to soak in both history and local culture!
Day 11 – Cinque Terre
Day 11 was spent in Cinque Terre, which means ‘5 towns’. They’re 5 little colorful towns on the rocky coast, about an hour train ride from Pisa.
Riomaggiore, Manarola, Corniglia, Vernazza, and Monterosso al Mare are all connected by train. It’s about a 5 minute train ride between each town. We stayed in the town of La Spezia, which was way cheaper than staying in one of the 5 famous cliff towns!
When we actually visited, it was a rainy day, but that didn’t stop us from enjoying our time! We had purchased a Cinque Terre Card online before visiting, which allows you to hike any of the trails and ride the trains between towns for free for the entire day.
Here’s a link to purchase the Cinque Terre Card for your visit:
https://www.cinqueterre.eu.com/en/cinque-terre-card
Here’s a breakdown of how we spent our day:
We started at the closest town to La Spezia, which was Riomaggiore. My goal was to visit each of the 5 towns in one day. Pretty much everything was closed, and there were maybe a handful of other tourists, which was fine with us! We would much rather explore places when they’re less crowded! So we hiked from the Riomaggiore train station up the hill and through the village, to get to the famous view point of the colorful village.
Next, we stopped at the picturesque town of Manarola. This is perhaps the most Instagram famous of all the towns, it’s so colorful and there’s a great vantage point to take photos not far from the town. This was probably my favorite of all the towns!
Next, we decided to skip Corniglia, since I heard that it wasn’t actually on a cliff, but inland a little bit. And, because the train only came through every hour, we had to use our time wisely. We decided to take the train all the way down to Monterosso al Mare, and then hike back to Vernazza and eat dinner there.
The hike between Monterosso al Mare and Vernazza was breathtakingly beautiful. It was difficult, since we had to hike up and down and around cliff like mountains, but it was amazing nonetheless! It took us about 2-3 hours to hike, and we would’ve absolutely taken longer if it hadn’t been a rainy day and if we hadn’t been hungry!
We finally made it to Vernazza at sunset, and had a great vantage point of the village from our hike! We found a spot to eat dinner, which was pretty much the only restaurant that was open, and ate some delicious pesto pasta! Cinque Terre was such a perfect way to wrap up a wonderful trip!
I really hope you enjoyed this overview of our trip to Italy! If you have any questions, please feel free to ask in the comments below!
Thanks so much for reading!
Megan
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