Italy: Five-Day Itinerary

Italy is one of our favorite countries, and after visiting it will be one of yours too. The people are lovely, the food is great, and the sites are magnificent. Rome itself is fantastic but pretty small so a lot can be done in a short amount of time. On this trip, you will spend one a day and a half in Rome before heading to Cinque Terre. Here we go!

Day 1

Arrive at the airport and take a bus or taxi to your accommodation. If you have to go through the Central Station (which you are likely to do at some point) beware of locals attempting scams with your train/bus tickets. Some people dress and act like they work at the station; they wear collared shirts, have lanyards with fake credentials tucked into their shirts and often have a pen in hand. They will kindly offer to assist you and then walk you to the automated ticket kiosks. We are not sure what happens from there, but we did see tourists following them and exiting the station. Exercise caution and keep an eye on your belongings. After checking in at your accommodations, find one of many small pizza places close to your place and eat all of the pizza they have. Then, head to the Colosseum. Be sure to buy tickets ahead of time and avoid the wait in line.


Spend an hour or two at the Colosseum before walking to and around the Roman Forum. From there, make your way to the Piazza Venezia, where the traffic is insane. You somehow have to cross the street without getting hit by a car… good luck! You only have a day and a half so let’s keep going. Walk over to the Trevi Fountain, and be sure to throw a coin behind your back while making a wish. They say that if you throw a coin in the fountain you are sure to return to Rome. The Trevi Fountain is bigger and more beautiful than pictures make it out to be, so don’t skip this site. The area around the fountain is also worth visiting; it is very crowded and full of pizzerias, gelato, and souvenir shops. The Pantheon and the Spanish Steps are the next stop. From there, stroll to the Via del Corso, one of the main streets in Rome for some window-shopping. For dinner, try to avoid the restaurants catered to tourists; Roscioli is a great choice.

Day 2

Today is another busy day. You have a train to catch in the early afternoon so wake up early and head to Vatican City first thing in the morning. If you happen upon a cafe that is open early, of course stop in and sit down for a cappuccino and pastry.


When you arrive in Vatican City first go to St. Peter’s Basilica. Entrance is free but you can buy skip the line tickets ahead of time. The line is long but it moves fairly quickly. St. Peter’s is the most beautiful church I’ve ever seen.


Next you have two options. You can 1) stay in Rome another day and visit the Vatican Museum or 2) do like we did and leave Rome after St.Peter’s Basilica. If you are a museum and/or art enthusiast you may want to stay. The Vatican Museum is quite big and there is a lot to see. If you are only interested in seeing the Sistine Chapel you will have to walk through the entire museum to get to it and the museum is usually very busy so it’s not a quick walk. If you do decide to go to the Vatican Museum, buy tickets ahead of time. If you don’t go, then get moving because you have a train to catch to Cinque Terre.


To get to Cinque Terre, you can take the train straight from Rome to Corniglia. You can buy tickets at the Central Station either the day of or the day before. Also, if you’re taking the afternoon train you will be arriving at night, when many establishments are closed. Grab something to eat later tonight if you don’t want a gelato dinner.

In Cinque Terre, we recommend that you stay in Corniglia, the middle town, for your entire stay; this way you can venture in both directions whenever you want. The train will arrive in Corniglia at around 9pm. There will likely not be any taxis or buses at the train station when you arrive. You can either arrange transportation with your hotel/Airbnb/hostel or you can do what we did and walk up a very long, dark flight of steps (365 is what they say). If you are bringing more than a backpack or a carry-on this may not be the best option for you.

Day 3

Let the hiking begin (or not)! Start your morning with a strong cappuccino breakfast at a one of the little cafés around town. Today you will be visiting the two northern towns of Cinque Terre: Vernazza and Monterosso al Mare. To get to each of these towns you can either hike or take the train. The train takes 10 minutes to get to each town. Hopefully you’re in the mood for some hiking though. From Corniglia expect about a two-hour hike to Vernazza. You will meet so many friendly people along the way and the views are spectacular. The hike is easy to moderate. Once you get to Vernazza, have some delicious pizza and gelato by the ocean. This little town is adorable, colorful, and it’s easy to stay there all day wandering the streets and people watching.


From Vernazza you can again hike (or take the train) to Monterosso al Mare. Again, this is an easy to moderate hike and it takes about two hours. Monterosso seems a bit bigger than Vernazza and has more of a “resort” feel than the other two towns. Monterosso also has the biggest beach, so take a beach day if you’d like! Explore the town and its cute shops and restaurants before taking the train back to Corniglia. Have dinner at Manana and, of course, have more gelato. How else are you going to try every single flavor?

Day 4

Today you’ll be hiking south to the remaining two towns. FYI: the hikes south are longer and more difficult than the hikes north. You may have a little difficulty finding the path, but there are plenty of other friendly people that will send your in the right direction and may even hike with you. One of our favorite things about Cinque Terre was meeting and talking to people on our hikes.


Once you find the path, you’ll start your hike to Manarola. The hike is moderate to difficult and will take over two hours. Don’t worry, you will be rewarded with some of the most scenic views and pizza. Repeat your routine from yesterday and stroll around town visiting shops and people watching. Feeling rested? Great! Now it’s time to keep hiking to the final town: Riomaggiore. The hike to Riomaggiore is probably the most difficult of all but it is definitely the best. You will want to stop every ten steps to take pictures of the landscape. Eventually, you’ll get there. We have one request while you are here: please go to a beautiful restaurant called A Pie’ de Ma’, where you will see the sun setting behind the ocean while enjoying some snacks and wine. After this magical experience, find a nice little pizza place and have dinner before heading back to Corniglia to have more gelato. You’re not tired of pizza and gelato, are you?

Day 5


If you thought things were going to slow down now, you thought wrong. Your last stop in Italy is the bustling and fashionable city of Milan. Buy train tickets ahead of time and arrive at the Milan central train station. Check into your accommodation (hopefully you have better luck than we did finding an OK place to stay for a reasonable price).


As soon as you are settled in, stroll down to Giardini Park, the Duomo and Galleria Vittorio Emanuele II. Stop for some AMAZING gelato at Cioccolati Italiani (the line is out the door). Then, walk over to Castello Sforzesco and sit at the park for a while. Later on, walk down to the Navigli District alongside the canal, which is lined with numerous restaurants, bars, art studios, performers and people selling crafts and wares. Have the perfect dinner at Osteria del Gnocco Fritto. The puffed bread still warm from the oven and the charcuterie alone are worth stopping in for.


The next morning you have the option to take a bus from the central train station to the airport or a taxi from your hotel. There will be cafes open early so stop in for that last morning espresso on your way to the station. Then resume dreaming of that gelato you had yesterday.