Steal My 12 Day Italy Itinerary

Trevi fountain in Rome, Italy

So, you’re planning an Italy itinerary…or dreaming of planning a trip to Italy? I know the feeling of frustration when you start thinking about all the places you want to see – the historic cities, the beautiful countryside, and everything in between. Should I spend more time in Florence or in Rome? Should I try to squeeze in the Amalfi coast, or plan a future trip to explore JUST this area? Can I see all of Cinque Terre in 2 days? I’m sure you’ve asked yourself these (or similar) questions while trying to plan and lucky for you, you just came across the perfect post! I’m going to outline my 12 day Italy itinerary for you to use for your next Italian adventure.

Figure out how long you’ll have in Italy

The first step to any trip is deciding how long you’ll travel for. You might be constricted by PTO days or have as much time to travel as you want. My only warning is to try not to cram too many destinations into a short trip. Take some time to explore and enjoy each place without being rushed.

I will admit that the Italy itinerary you’re about to read below is somewhat rushed compared to others out there. I could easily spend a month in each of these places and never run out of things to do, but my PTO days just don’t allow that! My advice is simply to enjoy your time and remember to let a few days go unplanned to see where the city leads you.

Let’s get into it!

Day 1: Fly into Naples

My assumption is that you’re coming from outside of Italy and the surrounding countries. The first part of this Italy itinerary is going to be along the Amalfi Coast and the closest airport and train station is in Naples. So, no matter where you’re coming from, just get to Naples and then to Positano. I recommend a private or shared transfer from the Naples airport (or train station) to your hotel in Positano.

–>Read more about how to get to Positano in this blog post!<–

Day 2: Explore Positano

Depending on where you’re traveling from, you might wake up super early this first day and my advice is to take full advantage of it! I woke up around 3am my first day in Positano, waited until the sun started coming up, and then started walking around the town. I loved seeing all the shop and restaurant owners get ready for their days ahead.

If you’re following this Italy Itinerary, you’re probably staying in Positano. This means you have the chance to get a unique view of the town before it becomes a tourist attraction. Day trippers will start arriving around 10am and then stay until the evening. Before and after they’re in town is a beautiful time to walk around and get more of the area to yourself.

There are a ton of shops around town that you can check out. I recommend sitting outside by the street for a couple meals during the day. You can relax on either of the infamous Positano beaches or even rent a scooter and explore the other towns along the Amalfi Coast.

–>Read more about things you won’t want to miss in Positano here<–

coastline of positano, italy

Day 3: Boat ride to Capri

There are ferries that will take you from Positano to Capri and back again! You can find the schedule here, but I recommend taking one of the earliest options to Capri and coming back to Positano in the evening. This will give you the most time on the island and let you explore as much as possible.

You can also opt to book a boat tour to Capri that will show you the different sites around the island including the Faraglioni Rocks, Blue Grotto, and more. You may even find an option that will anchor out at sea for you to swim on a warm day! I found my boat tour through Airbnb Experiences which had several options to choose from.

The option you choose should depend on whether you want to spend more time on land or in the water. The boat tour is going to be a lot more expensive than the ferries, but if you want to sail around the sea, this might just be the option for you.

faraglioni rocks in Capri, Italy

Day 4: Train ride to Rome

Today, you’ll be making your way to your second stop on this Italy itinerary! You’ll catch a ride (i.e., book a private or shared transfer or take the bus) back to Naples’ train station. You’ll then buy a ticket for Rome if you didn’t pre-purchase it online beforehand. It usually takes about 2 to 2.5 hours to make it to Rome.

Pro tip: if you choose to use the train’s Wi-Fi, it’ll make you confirm your identity using your phone. This only sticks out to me because I actually broke my iPhone in Positano and had to wait to go to an Apple Store in Rome since there weren’t any closer stores. So, I didn’t have a phone and I had a work meeting I was supposed to attend on the train ride. Well, I missed the meeting and had to explain to my boss that my phone stopped working and I couldn’t get on the Wi-Fi!

–>Read more about this tragically funny story here!<–

When your train arrives in Rome, head to your hotel and check in. If you still have some time, walk around town! Visit the Trevi Fountain and the Spanish Steps. Check out any number of shops and stores along the streets. Have an aperitivo before dinner.

exploring rome, italy

Day 5: Tours of the Roman Forum and the Colosseum

I used to not be a tour person and if that’s you right now, hear me out! I really only agreed to these tours because part of this trip was a group trip and a lot of it was pre-planned for us. However, I’m so glad it was! I would have never booked these tours on my own, but I’m so glad I got to learn about these historical places from someone who had lived in the area all her life.

I think it’s incredibly important to learn about the history of the place you’re traveling to – and especially ROME! There’s SO MUCH history here and there’s no way I would have been able to take away as much information as I did without a tour guide.

Not to mention, with tours like this one, you can skip the long line at these sites to see as much as you can in a day.

Roman Forum in Rome, Italy

Day 6: Tour of Vatican City

I’ll come right out and say it – I almost skipped out on the Vatican City tour. Like I told you above, I used to not be a “tour person” and I opted out of adding this tour to my itinerary. I planned to go see it myself. I’m SO GLAD I didn’t do that!

We had the same tour guide as we did the day before and luckily, I snuck into the last open spot in the group. We toured the Vatican Gardens, St. Peter’s Basilica, the Sistine Chapel, the Vatican Museums, and more. Again, we got to skip the line for all of this, so the tour is worth it!

Here’s an example of the tour we did.

Keep in mind that the tours on Day 5 and Day 6 won’t necessarily take all day. You’ll have time in the morning to grab a quick bite to eat and you’ll have even more time in the afternoon to explore more of Rome, have a slow dinner, and check out some of the nightlife as well!

St. Peter's Basilica in Vatican City

Day 7: Train ride to Florence

It’s time to head to our third destination and what happens to be my favorite city: Firenze!

You’ll probably find yourself surprised by how much you like Florence. It’s often overlooked as just another Italian city. I love it because it’s much more quaint than Rome, but busy enough to still be lively. That, paired with the Tuscan wineries you can find about 45 minutes from the city center and you’ve got a recipe for love.

The train ride from Rome to Florence takes about an hour and a half, so you’ll have plenty of time to either see more of Rome in the morning and hop on a later train, or take an earlier train and see Florence in the afternoon.

city views of Florence, Italy

Day 8: Tour of Tuscan wineries

This wouldn’t be a proper Italy itinerary without a tour through the countryside of Tuscany, including a winery or two. Even if you don’t drink alcohol – this area of Italy is far too beautiful to pass up.

We visited a total of three wineries and one olive farm. My favorite of the three was Castello Vicchiomaggio and this is what I would recommend if you only visit one.

If you opt to book a tour to several wineries, that’s also a good idea! They’ll likely pick you up in the center of town in a big van and then drive you 45 minutes to an hour away into the Tuscan Hills. We even opted to eat dinner at a small restaurant we came across in this area because you just can’t beat these views!

Tuscan winery in Italy

Day 9: Explore Florence

Now that we’ve seen the country, it’s time to experience the city! I made sure to put an extra Florence day in this itinerary because there’s so much to do and see around this city. I’d recommend visiting the Cathedral of Santa Maria del Fiore (aka the Duomo, or the big red dome in the center of the city), Uffizi Gallery, Accademia Gallery to see the Statue of David, wandering around the Piazza del Duomo, and more.

You can also see sweeping views of the city from Piazzale Michelangelo.

When we were there, there were a ton of street performers at night, so that was our nightlife. We did venture into one bar called One Eyed Jack that had live music and a fun vibe! They even started singing Sweet Home Chicago at one point which just really made me happy, being from Chicago.

Day 10: Train ride to Cinque Terre

On to the final leg of the trip! It’s around this time that you might start to feel down that the trip is almost over, but try to set that aside and be happy that you still have a few more days in Italy!

Cinque Terre is made up of 5 coastal towns that all connect via hiking trails and train tracks. They include Monterosso, Vernazza, Corniglia, Manarola, and Riomaggiore.

I’d recommend staying in one of the 5 towns of Cinque Terre when you visit. We actually stayed right outside Cinque Terre, but I wish I was more in the middle of everything.

Depending on which of the 5 towns you stay in, the train ride will take around 2 hours (give or take) from Florence.

I’d spend the rest of the day you have exploring the town you chose to stay in and grabbing a bite to eat.

coastline of Cinque Terre

Day 11: Explore the 5 towns of Cinque Terre

There are two ways to travel between each town: on foot or by train. The hiking trails are occasionally closed due to various reasons, so you’ll want to check before you go if that’s your prefered method. If they’re open, you’ll need to buy the Cinque Terre Trekking Card to gain access to the trails.

If you choose to explore by train, you’ll need to buy the Cinque Terre Train Card for access to the hiking trails and unlimited train travel for the duration of your stay. You can purchase either of these Cinque Terre Cards at any train station in the area, or you can do so online before you go.

Whichever way you choose to explore, try to take in each of these towns and notice the slight differences between them. They’re all similar, but also unique in their own way. I also urge you to try the pesto pasta here! This area is known for Pesto and it is seriously amazing!

Day 12: Train ride to airport and fly home!

The final day has come and if you followed this Italy itinerary, I’m sure you had just as good of a time as I had. It’s time to hop on a train to whichever airport you’re flying out of. That might be back in Naples, or it might be the closest airport which is Pisa Airport (PSA).

I hope you enjoyed this Italy Itinerary! It certainly brought back some very fond memories for me while writing it. Let me know in the comments below if you plan to use it (or part of it)!

Leave a Comment

The Comments

  • Ruby Rodriguez
    September 27, 2022

    Hi, i hope all is well. Thank you for sharing your Italy Itinerary 🙂 I have a question; do you have hotel accommodations you recommend in the various cities? Thank you in advance, Ruby

    • saraharnstein
      > Ruby Rodriguez
      November 2, 2022

      Hi there! Our hotels were chosen for us, so I didn’t do any research on hotels in the area. I’m sorry about that! I plan to go back to these cities on my own in the next year or two, so I should have more information then 🙂