After graduating university, my two best friends and I traveled Europe for three weeks to celebrate our last 4 years and our new degree! Italy was our fifth country out of seven, and we spent a total of five nights here.

In this blog, I’m going to give you a detailed itinerary of each day in Italy that you can use for when you plan a trip to Italy, whether while budget backpacking or on vacation with family!

Our itinerary at a glance:
Day 1: Fly into Milan + Train to Florence
Day 2: Exploring Florence
Day 3: Day Trip to the Chianti Wine Region
Day 4: Day Trip to Cinque Terre: Riomaggiore and Manarola
Day 5: Rome, Italy

Tip: We spent a total of five nights in Italy, and for 4/5 of them we stayed in an AirBnb in Florence for the convenience of having a “home-base” when doing little day trips. For our fifth night, we stayed in Rome so we could easily catch our flight out the next morning. Having a home-base in Florence gave us some much needed time to relax without having to worry about packing up our bags again in 1-2 days!

Day 1: The Afternoon in Milan

Our first day in Italy was a travel day as we took a plane from the Paris Beauvais Airport to Milan, and then from Milan we took a train to Florence.

When we landed in Milan, we took the airport shuttle bus directly into the city right next to Milano Centrale Railway Station, which is where we’d be catching our train later in the day.

We had a few hours in between our plane arriving and our train leaving, so we took the time to explore Milan! First, we dropped our bags off at a luggage storage so we didn’t have to lug them around the city with us. I highly recommend doing this because it isn’t expensive and it makes the few hours you have a lot more enjoyable – nobody likes lugging around a 10-20kg bag.

Since we left our AirBnb at 5:30am to take the metro and catch the plane to Milan, by the time we landed we were pretty hungry. I’m sure I had something to eat in between this time because I’m the type of person that has to have breakfast but honestly I can’t remember.

We found a quiet spot for lunch a few streets away from the Duomo, I would link the restaurant but honestly it wasn’t super impressive so I would recommend finding another!

We really only had time to eat lunch, enjoy gelato, and walk around the square near the Duomo before needing to get to the train station. But the last time I went to Milan (also for a day trip) I had a picnic in one of the parks nearby with focaccia from a local bakery – I definitely recommend doing this! It was so relaxing.

The train was supposed to take about 2.5 hours and arrive in Florence at 9:40pm, but our train stopped in the middle of its tracks for at least an hour and a half so we didn’t end up arriving at the station until about 11pm. From here, we took the bus to our AirBnb, but we also could have easily walked since it was nearby, we just weren’t familiar with the area yet.

Day 2: Exploring the Streets of Florence

Our first day in Florence, we slept in and started our day around 11:30am. We picked up a small breakfast from a cafe nearby our AirBnb (and the Duomo) and then started to explore the city!

Ponte Vecchio and an Italian Leather Market

We first crossed the Arno River on Ponte Santa Trinita to the north side, and then walked eastward to Ponte Vecchio. From here, we admired the historical bridge that was built in 1345 and that was the only bridge in Florence not destroyed during World War 2.

Along the bridge there are points to stop and take pictures, and also little shops to explore.

After Ponte Vecchio, we walked to the famous leather market called San Lorenzo Market. This market is outdoors and has tons of vendors – you can get an authentic Italian leather purse here!

Lunch in Florence

At this point, we were looking for a snack because it was the mid-afternoon and we had only a small breakfast. We came upon a trattoria called Trattoria da Guido that had been in business since 1961! I had an aperol spritz and a caesar salad, and finished off the meal with the classic Italian digestif, limoncello.

Everything was so good! I honestly wanted to come back for dinner just so we could try their pasta.

Good to know – a trattoria is a traditional local restaurant serving local cuisine! These are the best spots to try the local flare when in Italy. On the other hand, an osteria is where you are typically served wine with some light snacks.

The Statue of David and Where to Watch the Sunset

After our lunch/light snack, we went back to our AirBnb to refresh before our tickets to the Accademia Gallery which is where the famous Statue of David is on display. You will definitely need to book tickets in advance at least by a few hours (we booked the tickets the day-of) because there will be a very long line!

For the sunset, we picked up a bottle of wine and went to Piazzale Michelangelo, which is a famous lookout spot where you can see all of Florence. This is definitely a must-do activity, it was so beautiful. We decided to walk only halfway up the hill to watch the sunset because we already had a good view and we figured at the top it would be too crowded.

Dinner in Florence

Finally, to end our first day in Florence, we had dinner along the street of Via Calimala. I can’t find the name of the restaurant on Google Maps but my photo’s location shows that it is here!

I ordered their cacio e pepe which is one of my favorite pasta dishes and it lived up to my expectations for sure. Definitely try to go here if you can find it!

Day 3: Wine Tour in the Chianti Region

For our second day based in Florence, we explored the gorgeous region of Tuscany on a wine tour! This tour took us through Sienna and Chianti, and we stopped at two vineyards for a tasting. If you’re interested in taking the same wine tour, here is the link with more information!

Breakfast in Florence

To start our morning, we had brunch at Shake Café and it was a great way to fuel up for the day ahead. Also, I originally thought the café was going to be only tourists but there were actually quite a bit of Italians dining which made me like the café even more.

The Wine Tour

Our wine tour started at 2pm, and the coach bus drove us an hour south of Florence to the area of Chianti where we visited Greve and Siena.

On our first stop, we visited a small vineyard that only produces about 8,000 bottles of wine a year. Because of this, we were only given a little taste of each wine, and if we wanted more we had to buy a glass or bottle. This vineyard was beautiful but since it was small it wasn’t as exciting.

After our first stop, we drove into the town of Greve where we were allowed to explore for 30-45 minutes. My friends and I sat down at a super cute and small restaurant for a glass of the local wine while we were there!

Our final stop on our wine tour was at a much bigger vineyard called Poggio Amorelli, Castellina in Chianti, in the province of Siena. I absolutely loved this vineyard because our tour guide from the vineyard there was super enthusiastic to share his knowledge of the wines and the vineyard, plus our samples were much bigger here! We even tasted their balsamic vinegar and olive oils which were heavenly.

I would go on another wine tour just at this location! We even ended up buying a bottle of their rosé because we loved it so much and figured we can enjoy in later on in the trip.

Dinner & Gelato in Florence

When we got back to Florence that evening, we were eager to have dinner, so we took our tour guide’s recommendation of eating at her favorite restaurant, Il Paiolo. We had to wait a bit for a table, but it was well worth it because the host gave us each a glass of Prosecco as we waited, and we also had free bruschetta once we sat down! Here, I ordered their pasta carbonara and it was incredible.

After dinner, we tried out another one of our tour guide’s recommendations, which was her favorite gelateria called Carabè. This spot is so good!!

Originally, Rohini and I were going to split a cannoli and each of us were going to get gelato, but there was a bit of a language barrier so we each ended up each getting a cannoli and sharing gelato. It’s important to know that cannolis aren’t that popular in Northern Italy because they are Sicilian!

Day 4: Day Trip to Cinque Terre

For our fourth day in Italy, originally we had planned to go to Venice, but we hadn’t booked our train tickets so they were quite expensive. Instead, we took a day trip to Cinque Terre because the tickets were super cheap!

Cinque Terre, or the five lands, is know for it’s five towns that border the Italian Riviera coastline on the Ligurian Sea. We spent most of our time in Manarola and then finished our day in Riomaggiore. The other three towns are Monterosso, Vernazza, and Corniglia. I would have loved to spend more time exploring the other towns!

To give you an idea about the geography of Cinque Terre, here is a map of the towns.

Getting to Cinque Terre from Florence

The train from Florence to the first town in Cinque Terre, Riomaggiore, is about three hours. From here, you can hop on the train and easily reach the other four towns in between 2 and 10 minutes. These towns are very accessible by train!

Ending up in a completely different town than my friends on the Italian Riveria seems like a nightmare, but it actually was very easy to meet up with them again. The next train to take me to the other towns in Cinque Terre was only 5 minutes away, so I just hopped on the next one and then we were all in Manarola together!

Exploring Manarola

Manarola ended up being a highlight for me during our time in Italy. This town had a coastal charm that immediately pulled me in. I loved all of the colorful buildings and the easy access to the sea!

As soon as we stepped off the train in Manarola, we were greeted by a dozen or so Italian artisans! We strolled through all of the shops and found gorgeous jewelry and leather bags. I was so close to buying a leather bag but I simply didn’t have any room for it!

Lunch in Cinque Terre

After strolling through the stands, around 11am we decided to get lunch since we only had a small breakfast before the train. This happened to be a great time because we beat the lunch rush and didn’t need to wait for a table, and we had this amazing view of the street below!

We decided to eat at Trattoria La Scogliera, and here I ordered their sea bass ravioli. I think this was the best pasta I had in all of Italy. I still dream about it. Emma ordered a full sea bass and they filleted it right at the table!

After lunch, we explored the marina area and water, and also followed a path that gave us a great view of the whole town and all of its colorful buildings.

We wanted to go swimming so badly since it was a really warm day but we forgot to bring our swimsuits. Instead, we walked into the water about knee-deep and waded for a while. The water was so refreshing!

There were so many people swimming and cliff jumping, the relaxed and summer energy here in Manarola was amazing. I fell in love with this town so easily and wanted to spend another day or two here!

Exploring Riomaggiore

About an hour and a half before we had to catch our train back to Florence, we took the ferry from Manarola to Riomaggiore. We could have easily hopped on the train that took 2 minutes but we wanted to see more of the sea!

The ferry ride was very quick, but it was super cool to see the towns from another point of view.

I was really excited to visit Riomaggiore because the movie Lucas by Disney bases the setting from here! If you look in the middle picture below, you’ll recognize the buildings and the dock.

Riomaggiore would be the town to visit if you’re looking to do water sports. They had rentals for kayaks and you can even take a guided tour through the waters! We didn’t do this but it looked super fun.

Before heading to our train, I picked up fried seafood in a cone because I saw everyone walking with it and it looked amazing. For me, I am fairly new to enjoying seafood, so this was actually quite a jump for me. I didn’t love the calamari and shrimp, but I honestly think it’s because it was so fresh. Normally calamari and shrimp are my favorite types of seafood! My fried fish cone also came with little fried crab balls and those were so good.

As I enjoyed my fried fish cone, we made our way to the train station to head back to Florence for our last night. To reach the train station in Riomaggiore, you have to walk all the way up the street filled with shops, and then make your way around the cliff on the left side. It was a bit confusing for us, so plan extra time before your train!

Wood Fired Pizza in Florence

By the time we got back to Florence, we were ready for dinner! As we walked towards our AirBnb, we came across this restaurant called Cacio e Pepe. Surprisingly I didn’t order cacio e pepe since it’s my favorite pasta!

I was in the mood for pizza, so I ordered the “Four Seasons” with mozzarella, ham, olives, artichokes, and mushrooms. It was so tasty, plus they made my night because the pizza was in the shape of a heart!

After dinner, we went back to our AirBnb and packed for the next day since we’d be leaving early for Rome!

Day 5: The Eternal City, Rome, Italy

Our last full day in Italy was in Rome! We took the train from Florence at 7am and arrived by 8:30am. We first dropped our bags off at our AirBnb, luckily they allowed us to store them!

This was my second time in Rome, so I had done most of the classic sites, but I was excited to see them with my best friends because the first time I was here I didn’t love my company haha.

Breakfast, The Trevi Fountain, and the Colosseum

For breakfast, we tried out La Licata because it’s a really popular and highly rated breakfast spot on Instagram and Google. But, honestly I was disappointed. The croissant was very dry and tough, and the egg breakfast was mediocre. I would recommend just getting a bite from a bakery instead!

After breakfast, we went straight to the Trevi Fountain since it was still relatively early in the day so there would be less crowds. We lucked out and we’re able to get a photo without pushing through too many people!

By the time with saw the Trevi Fountain and explored some of the streets nearby, we had to head to the Colosseum because we had tickets reserved for 1pm. We had bought our tickets through Tiquets.com and this platform worked really well for us. We were able to skip the line and get right in! Be sure to book your tickets a few weeks in advance during the summer because the tickets sell out very quickly.

When we were on the second floor of the Colosseum, looking at all of the models and reading about the history, I ran into one of my closest friends / boss from Wildjoy! I knew she was going to be in Rome at the same time as me for her elopement, and we had planned to meet up later that night, but running into her at the Colosseum was a complete surprise! I had first seen her sister through the glass of of the exhibitions, and then next thing I know I see her fiancé round the corner screaming my name! It was so cool seeing them there.

An Italian Lunch and the Roman Forum

After the Colosseum, we were feening for some classic Italian sandwiches and we discovered this spot called Fuorinorma which is just a short walk from the Colosseum. This spot is an absolute MUST!! Everything was so fresh and delicious. I ordered their Uno which had spicy salami and provolone cheese, then I added roasted vegetables because they looked amazing. Definitely come here!!

We then went straight to the Roman Forum after lunch since it was right near by. I didn’t get a chance to explore the Roman Forum my first time in Rome but I’m so glad I could this time around.

Tickets to the Roman Forum are included with most tickets to the Colosseum so you don’t have to pay extra. Normally you don’t have a time slot and can go in within a 24 hour period of your reservation at the Colosseum.

The Roman Forum used to be the city center of ancient Rome, and today you can walk through and see their government buildings, where they held criminal trials and public speeches, and so much more. Definitely plan time to walk through, it’s well worth it.

Dinner & The Spanish Steps

After going to the Roman Forum, we went back to our AirBnb to relax and get ready for the evening. We still had our bottle of rosé that we bought from our wine tour in Tuscany so we decided to enjoy it during the sunset on the Spanish Steps before dinner!

For dinner, we wanted to eat at Mimi e Coco because Rohini’s friend who lived in Rome said it was her favorite spot, but there was a huge line so we decided to eat at a nearby restaurant instead. We decided on Terra di Siena and it ended up being pretty good. I had the gnocchi bolognese and for dessert we had tiramisu!

Drinks Above the Trevi Fountain

After dinner, we met back up with my friend Lacy for drinks above the Trevi Fountain at Hotel Fontana to celebrate her & her soon to be husband getting married within the next few days! This was such a special evening that we shared with them and I’m so glad we were all able to meet up in Rome!

Afterwards, we went down to enjoy the Trevi Fountain because it was so quiet being the middle of the night!

Day 6: Flying to Malta

Our last morning in Italy was spent taking the bus to the airport and then catching our flight to Malta. The last time I left Rome I had found a pistachio cream filled croissant to have on my way to Polignano a Mare, so I wanted to find another one that day. I was in luck because right where we got on the bus to the airport there was a little pastry shop inside the train station. I feel like this is my new favorite tradition to had a pistachio cream filled croissant in Italy because they don’t exist in France!

Also, if you are visiting Rome in a heavy tourist season, plan extra time to go to the airport because our bus sat in lots of traffic. We still made it in time, but I was worried we were going to miss our flight!

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I hope you enjoyed my detailed itinerary for spending 5 days backpacking Italy on a budget! I will be posting my itineraries for my last two stops on our backpacking trip, in Malta and Budapest, within the next few weeks.

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