Learn how I spent my two weeks in Italy as a first-time solo traveler! Feel free to take some inspiration on how I traveled around Italy for two weeks. In this itinerary, I’ll be visiting several Italian cities, such as, Rome, Florence, Venice, Milan, Amalfi Coast, Lake Como, and Capri.

Day 1: Flying in to Italy via FCO (Rome)

First Gelato in Italy

For my first day in Italy, I decided to visit several popular attractions in Rome such as the Spanish Steps and Trevi Fountain.

Pro tip: You’ll most likely experience huge crowds in Trevi Fountain. If you want to get a picturesque photo of the Trevi fountain with no crowds, try going to the fountain a little bit after sunrise.

Restaurants worth trying out in Rome:

Rifugio Romano – Trattoria

Osteria da Fortunata – Carbonara

Day 2: Day trip to Pompei and Staying in Sorrento

A view of Pompei

On day 2, I left Rome via Roma Termini and took a train to Napoli Centrale. From Napoli Centrale, I took the regional train to Pompei. It took me a while to find the regional train in Napoli Centrale because the platform was under construction and below the main station.

I arrive to the Pompei Scavi station around 12PM and explored Pompei until 5PM. From there, I took the regional train from Pompei Scavi to Sorrento and spend the rest of the night exploring the beautiful costal city.

Places to Eat in Sorrento:

Da Gigino – Trattoria

Porta Marina Seafood – Seafood Pasta

Day 3: Spending the Day in Amalfi Coast

If you want to save some money, go ahead and stay in Sorrento instead of Amalfi Coast. It only takes 45 minutes bus ride from Sorrento to Positano.


After you are done exploring Positano, hop onto a ferry to Amalfi. From Amalfi, you can take a bus up to Villa Rufolo and Villa Cimbrone.

Villa Cimbrone

Once you’ve visit Ravello, take the bus back down to Amalfi and spend some time exploring the beautiful coastal city

C. I. C. A. in Amalfi

During my time in Amalfi, the last ferry from Amalfi to Sorrento left at 5:00PM. From there, you’ll spend a little bit over an hour traveling back to Sorrento.

Must Try Street Food in Amalfi:

C.I.C.A. – Fried seafood mix

Day 4: Day Trip to Capri

From Sorrento, I suggest buying a roundtrip ferry ride from Sorrento to Capri. Once you’ve arrived there, try to take a boat tour around the island and spend the extra money to visit the Blue Grotto.

Entrance and Outside of Blue Grotto Capri
Blue Grotto in Capri

In the Blue Grotto, you’ll be offloaded to another boat where you’ll have to duck underneath the entrance of the grotto, as the entrance is quite small. Once you’re inside, you’ll see the water illuminate blue.

After the boat tour take a bus up to visit Anacapri. When I went, the bus line was quite crowded going up and coming back down. I believe I’ve wasted two hours waiting in line for the bus. If you do decide to go up, you would most likely be better off with a taxi.

Monte Solaro Chair Lift view

Once you’re in Anacapri, be sure to take the Monte Solaro Chair Lift to get one of the best views of the island. After the chair lift, be sure to check out Villa San Michele to get more amazing views of Capri.

Villa San Michele Capri view

Day 5: Traveling to Florence

View from Piazzale Michelangelo

Day 5 will be considered a traveling day. First, you’ll take the regional travel from Sorrento to Naples and from Naples, you’ll take the high-speed train to Florence. I left Sorrento at 8:30AM and managed to arrive to Florence by 3PM.

Day 6: Spend the Day in Firenze (Florence)

Florence is a very walkable city. Go checkout the Statue of David, Florence Cathedral, and the Uffizi Gallery.

Firenze All'antico Vinaio Sandwich shop in Florence

If you enjoy sandwiches, be sure to checkout All’antico Vinaio in Florence. There might be a line, but are also two other locations right next to each other. If you walk through Via dei Neri in Florence, it’ll be pretty hard not to spot the three different All’antico Vinaio locations clumped right next to each other.

Great Eats in Florence:

Da Nerbone – Tuscan Sandwiches, inside the Central Market

Trattoria Antellesi – Trattoria

Trattoria dall’Oste Chianineria – Florentine Steak

All’antico Vinaio – More sandwiches

Day 7: Half Day Trip to Pisa

In my opinion, visiting the city of Pisa shouldn’t take more than a day. Walking through the streets of Pisa between the train station to the Tower is an awesome experience! Though, besides viewing the Pisa Cathedral and climbing up the Leaning Tower of Pisa, I felt like I’ve done it all in Pisa.

So, if you’re staying in Florence, I suggest your Pisa itinerary to be leaving Florence early in the morning via the train. Then upon arriving Pisa Centrale, walk to the Tower (20-30 minute walk) and enjoy the Tuscany city. Once you’ve arrive to the tower, be sure to present your tickets to go up to the tower and take some breathtaking photos. Once you’ve come back down, you can go visit Cattedrale di Pisa or take the generic touristy photos of Pisa. After that, I would try and spend some time around the city until the evening.

My original plan was to go straight to Levante after Pisa to visit Cinque Terre on day 8. However, due to the rain, I decided to improvise and visit Bologna instead.

Day 8: Day Trip to Bologna

Due to the covered walkways, Bologna was an easy choice for my detour destination on a rainy day. From there, I took the San Luca Express up to Santuario di Madonna di San Luca.

Indoor Food Market in Bologna:

Mercato di Mezzo – Indoor food market to avoid the rain

Day 9: Spending the Day in Milan and Staying in Lake Como

On day 9, I packed by bags from Florence and began my train ride up to Milan. From there, I put luggage in a Luggage store in Milano Centrale and took the subway to Piazza del Duomo, which was conveniently located right next to Galleria Vittorio Emanuele II.

During my day in Milan, I first visited the Duomo di Milano Rooftop Terrace in the morning. If you love taking photos, you can easily spend a few hours up here. After the rooftop, you’ll climb back down to the Cathedral, where you’ll be greeted with a grand interior. Be sure to also check out the Underground museum of the Duomo. You can see some pretty cool artifacts and learn more about the history of the Duomo.

After the Duomo, I visited Palazzo Reale di Milano, which is an art museum located right next to the Duomo. Once I was finished with the museum, I eventually headed to The Galleria and walked around its vicinity until it was time for me to head back to the station.

Around 4PM, I took the subway back to Milano Centrale and boarded my train to Como.

Day 10: Lake Como

After spending the night in Como, I took a ferry to Bellagio and Varenna. One regret I made was not spending more time in Lake Como. One day is not enough to visit all of the lakeside villages in Lake Como and I felt that I could easily spend an entire week here. Lake Como was also fairly close to Switzerland, so doing a day-trip from Como to Switzerland would’ve been neat. Though, I was on a time crunch, so maybe I’ll be back in a few years to fully experience Lake Como.

Day 11: Trip to Venice

Venice is one of my favorite places in the world! Getting lost between the alleys and trying to figure out the maze-like city is an experience of it’s own. No matter where you end up, you’ll always see a hidden gem in Venice.

Day 12: Spending the Day in Venice

Some notable things that should be done in Venice is visit Doge’s Palace, Rialto Bridge, St Mark’s Square, join a food tour, and getting lost in the city.

Where to Eat in Venice

Ostaria Dai Zemei Crostini in Venice, Italy

Ostaria Dai Zemei – Crostini

Pasticceria Targa – Italian Pastries

Acqua e Mais – Fried Seafood in Venice

Gelato di Natura – Gelato

Gelato di Natura Campo Santi Apostoli Venice Italy
Gelato di Natura – Campo Santi Apostoli in Venice, Italy

Day 13: Traveling Back to Rome

Back to where we started, Rome. Leaving my B&B at 8:30AM, I managed to arrive to Roma Termini, Rome’s train station, at 2PM. From there, I checked into my hostel and began exploring the city.

Day 14: Visiting the Vatican

Visited St. Peter’s Basilica and the Vatican Museum.

Day 15: Exploring Ancient Rome

On day 15, I start off my morning with a tour inside the Catacombs. After the tour, I hopped on a bus to the Colosseum. After a few hours in the Colosseum, I head on over to the ruins of Rome.

Day 16: Traveling Back Home

On day 16, I had my flight at 9:30AM, so I had to leave my hostel by 7AM. If you managed to view my entire itinerary, you might have notice that my itinerary is all over the place and incomplete. When I have more time, I plan on refining this post and properly edit my photos and the content on this post. Thanks, if you manage to read the entire post. Hope this gives you inspiration or ideas on your trip to Italy!

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