Planning a trip to Italy and don’t know where to start? Same.
Well, not really. I went for the first time in 2013 and spent 2 weeks with my backpack and a Eurail pass and went where I felt like and it left an everlasting impression on me! Countless landmarks and historical monuments, I had only read about in school in addition to the delicious food had finally come to life! It was the icing on top of my first 50-day European backpacking trip.
I always said I’d return and it’s a shame it took a decade, but in the summer 2024 I was on my way there again, but this time holding the hand of my girlfriend Nicole who had never been.
Three weeks. Five regions. Countless pizza, pasta and gelato. Zero regrets.
This trip was a little more organized, because I knew exactly where I wanted to go and it was easy, because Nicole had never been before. We spent three full weeks exploring Italy from north to south — revisiting some of my favorite places and discovering new ones together!
Floating through Venice’s canals, sipping wine in Tuscany and gallivanting through Rome, this itinerary gave us the perfect balance of iconic sights, food comas, and leisure travel.
If you’re planning your own Italy adventure, here’s exactly how we structured our trip with stops, dates, and what we loved most about each place and what we’d do again.
I feel that it’s the perfect – sampler if you will – a mix of iconic cities, slow mornings, smooth train rides, and spontaneous day trips that were highlights of our journey.
✈️ Getting There: LAX → VCE
July 10, 2024
Using our Chase points we accumulated using our Chase Sapphire credit cards, we were able to purchase tickets through Air France from LAX to Venice Marco Polo International (VCE) with a short layover in Amsterdam Schipol (AMS). Yeah it was a long flight, but we kept ourselves entertained and with the thought of landing in Italy made everything worth it!
📍 Stop 1: Venice
July 10, 2024
I remember exiting Santa Lucia train station for the first time in 2013 and being met with the sight of the iconic Grand Canal. Venice is like walking through a living museum. Every corner looks exactly what you’d see on a postcard in the best way possible.
During my first visit, I remember staying in a hostel somewhere in the city center. It was okay. But as a solo traveler, I didn’t mind. All I need is a roof over my head and I’m all good! But now that I’m traveling with my partner, I can’t settle for the bare minimum anymore. I want her to be comfortable.
To stay in Venice proper is a lot more expensive these days, especially during peak season like summer; however, we were able to find a decent hotel/hostel in Mestre, the city just a 10 minute train ride away to Venice.
Where we stayed:
Meninger Venezia Mestre
This is a hotel/hostel that was very clean and a 5-minute walk to the Mestre train station. You can purchase a one-way ticket to Santa Lucia for €1.50 and be in front of the Grand Canal in 15 minutes.
What we loved:
Getting gloriously lost in the narrow alleyways
St. Mark’s Square at golden hour
Day trip to the islands of Murano and Burano
Aperol spritzes and pizza by the canal pretending we’re locals
Vibe
Romantic, surreal, and slightly chaotic — but in a charming way. It was summertime, so we anticipated it to be crowded; however, if you really want to get away from the crowds. Visit Murano or Burano around mid-afternoon. Nicole and I were able to enjoy the sunset with very few people around.
Two nights felt perfect here. Venice is compact, so you can see a lot without rushing.
📍 Stop 2: Lake Como – Bellagio
July 12 – July 14 (2 nights)
We hopped on an early-morning train from Venice and headed north to Lake Como. We had a short transfer in Milan, but once we got there…wow… just wow! This was our first time in Lake Como and it blew us away. We bought a last-minute ticket for a ferry from Como to Bellagio, which took about 2 hours, but it’s actually a great way to survey all of the cute, little villages all along the lake. Ah! Just writing about it just makes me want to go back so bad! We took a day trip to Varenna, which also took our breath away! I think WHEN we go back, we would probably like to stay there to change it up, but I recommend staying in Bellagio. It’s such a beautiful town!
Where we stayed:
Apartments by Wonderful Italy
We rented a full apartment in Bellagio from Wonderful Italy (I recommend them) and had a wonderful view of the lake and a 5-minute walk to town.
Highlights
Ferry hopping between Como, Bellagio, and Varenna
Sitting by the water doing absolutely nothing, but admiring the mountains, crystal clear water and colorful lakeside towns
Eating pizza while staring at mansions and yachts we can’t afford.
What we’d do next time:
- Stay in Varenna (just to change it up)
- Visit Villa del Balbianello this is where Anakin and Padmé were married in Star Wars Episode II: Attack of the Clones
- Explore more of the small little towns along the lake.
Vibe
Calm, luxurious, and unreal views at every turn.
Short stay, but it was the perfect reset before heading south.
📍 Stop 3: Amalfi Coast
July 14 – July 18 (4 nights) | Base: Piano di Sorrento
We based ourselves in Piano di Sorrento at a beautiful and boutique bed and breakfast: Secret Garden Relais. Piano di Sorrento is a lot cheaper and quieter than Sorrento, Positano or Amalfi — and honestly, after visiting those places, it was a smart move. Piano di Sorrento has some restaurants and beautiful views of the ocean (since it sits on top of a cliff), but it’s a great place to set up a home base while you travel around the Amalfi coast. From there, we did day trips to some of the popular spots along the coast.
Where we stayed:
Secret Garden Relais
This is probably Piano di Sorrento’s best kept secret! We found this colorful 18th-century villa turned charming bed-and-breakfast on Booking.com! It’s about a 6-minute walk from Piano di Sorrento train station, which made day trips very easy! What we loved the best was that how tucked away the property was and that you had to walk through a beautiful garden to get to the entrance. We also enjoyed that breakfast was included and served on a beautiful and quaint terrace.
The Day Trips…
🍋 Sorrento
This was easy to get to by the circumvesuviana train. It’s €1 and like a 4-5 minute ride. There’s a lot more to do in Sorrento. A lot of shops, restaurants, markets, cute shops and beautiful ocean views!
🍕Naples
My friend Claudia and her family were in Naples during the time we were visiting. So we went and visited them. We also took a trip to Sorbillos, THE BEST Neapolitan Pizza you will eat. Claudia introduced me to them the first time I visited in 2013. I was so glad they were still around and even better that Nicole got to try it. Otherwise, there are some great attractions in Naples if you’re into history.
🌊 Amalfi & Positano
Nicole and I booked a day trip tour to both Amalfi and Positano. It was more of a combo boat ticket that gave you a few hours in each city before moving on, which was more than enough time. Both Amalfi & Positano are magnificently beautiful towns with scenic photo opportunities everywhere you go. The only draw back was that they were outrageously, obnoxiously crowded! However, perhaps next time we would like to stay at either one and maybe go even further south.
🏛 Pompeii
Walking through an ENTIRE city frozen in time was wild. I had visited once before, but in a span of 10 years of course they’d uncover more. I explored it on my own the first time, but we had a guided tour this time around and I 10/10 recommend a guided tour so you actually understand what you’re seeing and know the countless stories behind the ruins.
📍 Stop 4: Florence
July 18 – July 25 (7 nights)
Alright let me tell you guys something, out of all of the places I visited in Italy, Florence had stolen my heart this first time. So many stories from the time I was there, I KNEW that Nicole would love this place and I knew there would be so much to do and see. So Florence became our home base for a whole week, and it was perfect, I mean perfect.
Where we stayed:
Residenza Ponte Vecchio Firenze
We stayed near Ponte Vecchio in an apartment, which made wandering around insanely easy!
Check it out on Booking.com!
What we did in Florence:
Duomo of Santa Maria di Fiore and many other cathedral views every day
Sunset at Piazzale Michelangelo several times
Uffizi Museum and the Leonardo Da Vinci museum
Walking tours throughout the city.
A pasta cooking class at a private villa and vineyard
Eat at a restaurant for lunch and dinner every day
Our Day Trips from Florence…
Siena & San Gimignano
We spent a day taking a train and bus to these small towns in the middle of the Tuscan countryside. Medieval vibes, rolling hills, and towers everywhere. Nicole and I were able to get away from the crowds and take some amazing photos.
Cinque Terre
We took a train and spent a full day in Cinque Terre. We considered staying a night in one of the towns and if we did, I would have chosen Varnazza. You can actually hike to each village, which I heard can be very strenuous, but a lot of the trails were closed, so we decided we’d do it the next time. We took the short Cinque Terre express to each of the five colorful cliffside villages. We did a bit of hiking, some swimming, and took a LOT of photos.
Pisa
This is a half – if anything, a quarter of a day trip. We just went to take our cheesy photos. “Ha Ha look at me I’m holding it up with my hand” and were back in Florence before dinner.
Tuscan Cooking Class
We booked our cooking class through Walkabout Tours and were blessed with Luca and Lucia. If you can get them to do the class, you will not be disappointed. Luca made the class so entertaining. One of our favorite experiences that included:
- Local wine
- Eating what we cooked like proud Italians
- Cooking homemade pasta and tiramisu at a private villa and vineyard with a beautiful view of the Tuscan countryside.
Vibe
Art, wine, history, and slow evenings wandering cobblestone streets.
📍 Stop 5: Rome
July 25 – July 29 (4 nights)
Final stop: We finished our Italian trip in the eternal city, Rome — loud, historic, and absolutely epic. The last time I visited Rome, I spent a whole week there and I got to know the city very well. There’s a lot to see and do, though not as nice as the other cities since it’s a capital metropolis and all. In 4 days, we managed to see all of the top attractions! We even spent a day with my mother who worked on a flight over to Rome.
Call it what you want, but the first time I was in Rome, I did throw the 2 coins in the fountain. Legend says if you throw 1, you’ll return to Rome, if you throw 2, then you’ll return with your true love…
Where we stayed:
Apartment in Rome
We stayed in an apartment near St. Peter’s Square and the Vatican.
Must Dos:
Colosseum
Stepping inside the Colosseum feels like time traveling straight to Ancient Rome. It’s hard to believe gladiators once fought there in front of tens of thousands of spectators. It’s also amazing to think that after all of these centuries, it has remained standing!
Book a skip-the-line ticket or guided tour if you can — it adds so much context and saves you from melting in the summer heat.
Roman Forum & Palatine Hill
Right next to the Colosseum is the Roman Forum & Palatine Hill. This is where ancient Rome actually lived. Travel through time by wandering the ruins of temples and government buildings. After a day of walking, you’ll feel the scale of how massive the Roman Empire was.
Wear good shoes and take your time — this area is enormous and full of hidden corners that most people rush past.
Vatican City & Museum
Vatican City holds the title of “smallest country on earth” as it covers less than half a square mile but holds some of the greatest artistic treasures on Earth. The Vatican Museums stretch over more than four miles of galleries and house thousands of works collected by the Catholic Church over centuries. Walking through them feels endless in the best way, eventually leading to the famous Sistine Chapel, where Michelangelo spent four years painting the famous ceiling with over 300 figures. Just outside the museums, St. Peter’s Basilica stands as the largest church in the world and one of the most impressive architectural achievements in history. Its massive dome dominates Rome’s skyline and offers breathtaking panoramic views if you climb to the top.
Pantheon
The Pantheon is one of the best-preserved ancient buildings in the world, standing strong for nearly 2,000 years. Its massive concrete dome and open oculus allow sunlight to stream inside, creating a dramatic and peaceful atmosphere. What makes it even more special is that it still functions as an active church today.
Spanish Steps
The Spanish Steps are one of Rome’s most iconic meeting points and a great place to pause and soak in the energy of the city. Standing at the top and people-watching during sundown was one of our favorite simple moments.
Pro tip: Eating on the steps is no longer allowed, so enjoy your snack nearby and save yourself a fine!
Trevi Fountain
The Trevi Fountain is even more stunning in person than in photos. Like I mentioned before (if you read my entire post 😉), tradition states that if you toss a coin over your right shoulder to ensure a return trip to Rome — we didn’t question the tradition, we just went with it. Visit early morning or late at night if you want to avoid the shoulder-to-shoulder crowds.
Vibe
Controlled chaos, but in the best way. You’ll walk 20k steps guaranteed and still feel like you didn’t see everything. There’s literally some significant monument or artifact on every corner in Rome.
Final Thoughts
This itinerary was an “Italian Antipasto”. It gave us:
✅ Big cities
✅ Relaxing coastal towns
✅ Day trips
✅ Food experiences
✅ Culture overload (the good kind)
If I had to do it again?
I wouldn’t change much at all other than staying longer in Como or Amalfi or maybe visiting some other cities like Matera or even visiting the island of Capri.
I feel that this itinerary is a great way to see most of the iconic cities of Italy in 3 weeks. Even if you have 2 weeks, you can scale this itinerary to see Venice, Amalfi, Florence and Rome and still have a remarkable experience.
