Two Weeks in Italy: How to make the max out of your trip!

Buongiorno darlings,

It was a grey January day when one of my roommates told me she dreamed of traveling to Italy. We spent that evening discussing all the places we would love to visit. Because of our work schedule, we had a vacation coming up and decided we would spend two weeks traveling by car all around Italy.

How fortunate were we: we only had a few more weeks until our winter vacation from work, where we could escape the gloomy Parisian weather and relax in the warm Italian sun. We were extremely excited about a change of scenery and experiencing the beauty of Italy.

I researched how to organize the trip and hit all the major Italian cities in two weeks. Early on, we decided to rent a car for most of the trip and divide the costs between 5-7 people. This was the best decision for us since (1) we would split the costs, and (2) we would have the liberty to change our plans as we wished. It ended up being one of the best decisions for this trip, and we enjoyed so much driving around Italy.

As for the cities: because many of us hadn’t been to Italy before, we agreed that this would be a trip where we visit every major city instead of spending more time in one region. We preferred hitting all the cities and then, hopefully in the future, having time to decide which region we wanted to explore more of (I’m dreaming of spending a lot of my time in Tuscany). With these two things in mind, I created an itinerary for our two weeks. We planned to make stops between big cities and explore smaller towns. Without further ado, I share our Italy trip.

Day 1: Arrival in Milan

We began our holiday early Saturday morning, flying from Paris to Milan. I dedicated only one day to Milan since we had a few things on our list and wanted to visit Lake Como. Milan deserved more than just one day; however, based on our trip, I don’t regret dedicating only that day to Milan. I do recommend looking into visiting Milan for a weekend trip.

Our first day was spent wandering around Milan, visiting the Last Supper in Santa Maria delle Grazie, the Duomo, and Galleria Vittorio Emanuele II while taking in all the beauty in Milan. We stayed in the YellowSquare hostel near the metro station that would connect us to the center within 10 minutes. We loved this place and found it conveniently located. We didn’t eat much in Milan (I know, insane). I think because we only had one day, we spent most of our time walking around than sitting down to eat (don’t worry, this changed throughout our trip). However, one place we did try and loved (and I now see on TikTok quite often) was Trapizzino Milano. The food was delicious. The restaurant serves folded-up pizza (the best way I can describe it). We then returned to our hostel to rest up for our big day on Sunday.

Day 2: Lake Como

I was extremely excited when I woke up. I dreamed of visiting Lake Como for years, and that Sunday was the day to make my dream come true. I. Fell. In. Love.

We woke up early (around 7 am) to take a direct 1-hour train to Varenna-Esino. We paid 14 euros round trip for the train. When researching, there are various cities that you can connect to by train when leaving from Milan. I chose Varenna since I saw a few pictures and wanted to walk around. We all wanted to visit Bellagio as well. From Varenna, you can take a ferry for 15 minutes for 7 euros round trip to Bellagio. Since we went in late February, there weren’t many people, and we could buy the ferry tickets at the station. I do imagine that in warmer weather, there might be more lines; purchasing ferry tickets online in advance is also an option.

We spent the whole day in Como and enjoyed lovely strolls around the lake and the small towns. As it was Sunday, there weren’t many places open. However, we enjoyed walking along the quiet streets, enjoying our time, and taking the day slowly.

We found a restaurant that it’s name I cannot recall. This was our first proper Italian meal of the trip, and we had the best dishes to start our journey perfectly. We continued walking through Bellagio and spent around 4 hours exploring the town. We headed back to Varenna to explore a bit more. By sunset, we wanted to sit by the lake, enjoy some limoncello spritz and cherish that last bit of sun. We sat down at Ristorante Vecchia Varenna and had the most magical time.

Sadly, by 7 pm, we had to return to Milan. Upon our arrival, we were craving some pizza and popped into Berberè Pizza near our hostel, where we enjoyed some delicious pizza. We returned to our hostel to prepare to pick up the car and start our drive around Italy.

Day 3: Bergamo, Verona and Venice

We woke up bright and early since we had a long drive ahead: we were going to Venice! Before heading straight to Venice, we had mapped out two stops in between: Bergamo and Verona.

Our first stop was Bergamo. This is a gorgeous medieval hilltop city with stunning views of the country. We spent most of the day walking around the city, taking pictures, and exploring this town's magnificent architecture. For lunch, we stopped at Il Fornaio where I had the most exquisite focaccia I have ever tried. I have never had something more delicious than this fantastic focaccia. We ordered a few to share: classic focaccia with olive oil and one with arugula, tomatoes, and basil. Nothing will ever top this.

We headed back to the car and drove down to Verona. Now I have to admit that I was obsessed with the movie Letters to Juliet for more time than I would like to admit. I have always wanted to visit the city and let me just tell you it is worth the stop. I recommend spending a weekend exploring all this beautiful city offers. We didn’t have much time in Verona; it was getting dark, and we wanted to arrive in Venice soon. However, we had a chance to see the infamous Juliet statue and even write letters to her writers, just like in the movie.

We got back in the car and made our way to Venice. We left the car near the train station and walked to our Airbnb. It was around a 20- minute walk; I didn’t think about all the tiny bridges we would have to cross when packing. For this reason, I recommend packing only the essentials, as the over-packer in me was tired by the time we got to the house. Our Airbnb was gorgeous, and its views of the canal were priceless. We immediately passed out as soon as we got there.

Day 4: Venice

We only had one full day in Venice. Looking back, if you have never visited Venice, I recommend adding another full day.

We began our day crossing the grand canal and heading to the San Marco area, where you will find Basilica. Most of the day was spent (you guessed it) walking around Venice. Meg and I purchased some delicious Aperol Spritz while we enjoyed our stroll (we got some iconic pictures of Meg with her spritz). We had a quick lunch at an Argentinian restaurant and continued our walk. One thing I wanted to do in Venice was sit down at the famous Cipriani bar (Harry's Bar) and have its iconic bellini. We spent some time enjoying our drink while people-watching. After our drink, we got a gondola ride for 80 euros (16 euros per person), enjoying our last ride around Venice. We had dinner at a small restaurant and then returned to the Airbnb to prepare for our next day.

Day 5: Bologna and Florence

We were heading to Florence! But before that, we made a stop in Bologna. I cannot emphasize more that Bologna not only needs to be a stop but a whole week's trip. I fell in love with Bologna and thought I needed more time there. We had two goals for Bologna: try their gelato and have bolognese sauce.

We sat down at 051 Osteria, where I kid you not, I had the best lasagna of my life. This was an authentic experience in itself. There are no words to describe this dish, and I am so sad I don’t have any pictures. The sauce was creamy and smooth, while the pasta was perfectly cooked. It was one of the best thing I ate during the whole trip. Before heading to Florence, we had to try a gelato from Cremeria Santo Stefano. I had their crema delle zitelle (a mascarpone gelato) with chocolate sauce on top, which was insanely good. This was another experience. That gelato was something else that I dream about every day.

We got back in the car and headed to Florence. We arrived around 6 pm and briefly walked to see a few things. We passed the famous boar statue (and touched its mouth) before heading back to the Airbnb to rest up.

Day 6: Florence

We woke up bright and early. Meg made some scrambled eggs with tomatoes while I prepared the coffee for everyone. We hada day full of activities. We began visiting Il Duomo (although we would go inside another day) and then headed to SantaMaría Novella. Since my first year of college, my friend had shown me this gorgeous perfume shop from Florence. It is one of the world's oldest pharmacies and perfume shops, established in 1221. Now, you can find one of the most beautiful shops int he world. This is a must-visit in Florence. We spent the rest of the day walking around, exploring Florence.

Day 7: Florence

Our first stop was to de Galeria dell’Accademia, where we saw theDavid. We spent a few hours wandering around until it was lunchtime. For our lunch, we saw a restaurant a few days before that looked amazing but was always full. This day we went a bit early to secure a table, and thank god we did because this was one of the best meals I have had in a while (I feel like I am constantly repeating this phrase). We spent around 3 hours in this meal, and I had to order two different kinds of pasta because they were insane.The restaurant is called Vini e Vecchi Sapori, and I cannot recommend it more during your visit to Florence.

After our extended lunch, we headed to the Duomo, where we finally saw the magnificent dome. We walked a bit more and foundFlorence’s leather market. We spent most of the afternoon perusing around the market. My friend, Jasmin, had told us about this leather store called Massimo Leather. They have some beautiful purses and leather goods! We headed to the store, and I found a gorgeous leather blazer. Massimo is such a wonderful person, and he quickly tailored the jacket to fit me perfectly.

Day 8: Florence

Jasmin and I woke up a little late, looking for an Italian breakfast and coffee, and decided to stop at Caffe Gili. We stood at the bar and ordered a cappuccino (before 11 am) and a decadent croissant filled with Nutella. The caffe was gorgeous and so luxurious.

We then headed out to meet with our group, where we walked along Ponte Vecchio. We wanted to go to the Uffizi Gallery but needed to get our tickets earlier. What else could we do but head out for lunch? We had made a reservation for 4 Leoni; this was another incredible restaurant. I had one of the best bistecca alla Fiorentina and Jasmin had her best tiramisù. Another fantastic restaurant to add to your list.

After another extensive 3-hour lunch (well worth it), we wanted to walk off our fullness and headed to the Piazzale Michelangelo to watch the Florentine sunset. We enjoyed the views and the gorgeous time with friends as this was our last night in Florence.

Day 9: Pisa & Rome

We were so sad leaving Florence; this was a highlight of our trip, and we had an amazing time. But we were heading to ROME!

Before arriving in Rome, we had planned to make a pit stop in Pisa to see the leaning tower. This is the perfect plan to visit the tower.Pisa is a small town; I would allocate half day to making the trip and seeing the tower. We spent around 1 hour and 30 mins in Pisa, walking around and enjoying the town before returning to the car and making our way to Rome.

Upon our arrival, we immediately headed to the Trevi Fountain to throw our coins and make a wish. We walked a bit before returning to the Airbnb to rest for our jam-packed day.

Day 10: Rome

We woke up to the beautiful Roman sun and headed to thePantheon for our tour. We then walked around Rome until we reached the Colosseum and sat down for a quick Aperol Spritz.Since we couldn't get tickets for the Colosseum, we walked around until we found a gorgeous spot to take a few photos. In this place, we took the picture that inspired my whole brand as the colors of this wall inspired me to start my Instagram and begin working on my website.

One mistake we made in Rome was expecting to be able to visit famous attractions and find tickets on the same day. This was not the case, and it took a bit more planning. We could only go inside the Colosseum on our last day, and it was a hassle to find tickets. I highly recommend planning out the famous places to visit beforehand. I researched a few ways to go about it and suggested looking into the Rome day or two-day passes that give you access to all the main attractions. We then returned to our Airbnb to rest before dinner at Virginae to have the infamous Cacio e Pepe.

Day 11: Rome

I woke up early in the morning and headed out for a quick breakfast before roaming the streets of Rome. I wound up at Giolitti, a famous gelateria in Rome, and although it was only 9 am, you best bet, I had a gelato. With a gelato in hand, I made my way to the Spanish Steps.

I returned to our apartment as some friends were leaving, and I offered to drive them to the airport. Meg and I decided to walk near the Vatican and have a coffee before leaving. We had a chat, and then I took her to the airport.

I then met up with my friends at the Vatican, where we bought tickets to the Basilica. Now, this was our other mistake: we had booked the 3 pm tickets and didn’t realize that the Vatican would close at 4:30-5 pm. So we only got to see the Basilica and could not see the Sistine Chapel. Like the Colosseum, I recommend planning all the tourist attractions with time and allocating a designated day for each one, either in the morning or early afternoon, to ensure enough time to see everything.

Day 12: Rome & Naples

It was our final day in Rome, and we were heading to the Amalfi Coast! We decided to stay in Naples for a few days and then drive to the different cities around the coast.

This was the first car ride where we didn’t have any cities planned between driving from one town to the next. We put on our roadtrip music and headed down to the coast.

We arrived in Naples just in time for dinner and went to find some good pizza. We found a small place our Airbnb recommended and had delicious Neapolitan pizza. I couldn’t recall the name, but trust me, Naples has some incredible pizza.

Day 13: Pompeii & Sorrento

We woke up early to start our journey through Pompeii and Sorrento.We headed to Pompeii and visited the ruins for a few hours. I recommend booking the tickets a day or two in advance. After our tour, we continued to Sorrento, where we had one of the best lunches on our trips. We found this restaurant called Il Leone Rosso. When I tell you they gave us so much free food and pampered us in the best way possible. I fell in love with this restaurant and highly recommend visiting. We ended our lunch with some delicious limoncello and then strolled around the gorgeous streets of Sorrento.

Day 14: Positano

Cue Quando, Quando, Quando by Tony Renis as you drive down the coast with your windows, rolled down, enjoying the magnificent view. THIS was a magical ride as we saw the gorgeous towns and cliffs on our way to Positano.

Now, because it was only early March and still a bit cold, we couldn't enjoy all the magic of Positano. But we could still get some sun and dip our feet into the ocean. We began by trying to find parking; if you are renting a car, this will be your biggest struggle when on the Amalfi Coast. Since we already had a car, we spent around an hour looking for parking. I recommend finding another way of transport to Positano, not requiring you to park.

We headed down the millions of stairs (beware, there are so many stairs) and strolled along the town's small streets. When we finally hit the beach, I was mesmerized by the gorgeous views of the cliffs. We sat down in one of the restaurants on the beach to enjoy some limoncello spritz while taking in all the beauty. We spent the whole afternoon like this and did not regret it. We then headed back to Naples.

My Recommendations

I’ve mentioned a few things throughout this article that I would keep in mind when traveling to Italy.

-I recommend researching and deciding which tourist attractions you want to do in each city, getting tickets for those in advance, and planning the days for each activity.

-We had originally planned to visit Pisa after our stop in Bologna but had to make changes. It is a relatively short drive from Bologna and Florence, therefor you can decide when to visit.

-I cannot recommend more allowing parts of your day to wander through each city as you may be surprised by what you find.

-Safety: although we felt pretty safe in almost every city, we had few not-so-grand situations in Naples. Make sure to be aware of your surroundings and your belongings in Naples. It's a beautiful city, but you should be mindful of certain more dangerous areas.

-Visiting during the off-season: for most of the places we visited, we found them to be quite enjoyable and not filled to the brim with so many people. The only place we considered not going was to the Amalfi Coast as we preferred warmer weather. I always recommend visiting just before or after peak season (April-May or September-October), but the trip was perfect for us.

-Pack lighter or plan ahead your outfits. I brought many things I never needed and ended up carrying my heavy luggage all over wishing I had packed less. Bring comfortable shoes (an espadrille-when weather permits- and some cute sneakers are a must)

-Overall, my biggest recommendation is to do research and find what fits best for you.

For this trip, we decided to hit all the cities, and yes, by the end, we were a bit tired, but we didn’t regret anything.

This trip opened our eyes and made us dream and plan other trips to Italy to focus more on regions/places we missed.

-I will mention that each city can be (and should be) visited between 3-5 days (depending on the city). Cities such as Florence,Rome, and Venice can also be planned during a weekend trip, for example.