I have learned that my favorite way to travel these days…is slowly. I used to hop around Europe staying in a different city every two days (and sometimes I still do), but my new travel style is so much more relaxing. I often get asked for travel itinerary suggestions, so I’m sharing the itinerary I created for my month-long stay in Italy in September 2022. If you’re taking a shorter trip, this 4 week Italy itinerary can be adapted to fit your needs and schedule.
Itinerary Overview
Total: 27 nights
Desenzano Del Garda
Why I Chose This Location
I visited Lago di Garda in 2016 and spent 2 nights in Sirmione. It’s a lake halfway between Milan and Venice. When I first arrived at the train station in Desenzano, I fell in love with this adorable little town on the water, specifically the small boats in the middle of town surrounded by restaurants. The area was absolutely beautiful and, surprisingly, not crawling with American tourists like Lake Como. I knew I wanted to eventually come back and see more.
On this trip, I wanted to make it as easy as possible to get to where I was staying, so Desenzano was an obvious choice for me. From the train station, it’s about a 15 minute walk downhill to the city center, which is right on the water.
How I Got Here
- I landed at the Milan Malpensa airport and took a train from the airport (Malpensa Aeroporto T1) to Milano Centrale (54 minutes), and then Milano Centrale to Desenzano del Garde/Sirmione (1 hour and 23 minutes). Total time with connection: 2 hours and 35 minutes
- Timing details: My flight was scheduled to arrive at 9:30 am, but we were delayed and arrived at 9:50 am. I had my bags by 10:30 am and took my time as I waited for my train into the city at 12:13 pm, arriving at Milano Centrale at 1:07 pm. I had 18 minutes between trains and my train to Desenzano left at 1:25 pm, arriving at Desenzano del Garda/Sirmione at 2:48 pm.
- ***I bought my train ticket on the Trainline app the night before while I was at the airport waiting to depart***
Where I Stayed
- Attic Airbnb in the center of town
What I Did
- Vintage driving tour around the lake in an Alfa Romeo Spider convertible
- Sunset sail on Lago di Garda
Florence
Why I Chose This Location
You’re probably going to ask me, “Terry, why would you spend 2 weeks in Florence?!” Yes, I admit it’s a long time, and this was my fourth visit. However, my first two visits to Florence were insanely short (1 night and 2 nights). When I visited in 2021, I fell in love with the city and stayed for a week, which ended up still not feeling like enough time for me.
I originally had wanted to spend one of the weeks taking Italian language classes, which I did the previous year, but ultimately decided not to. I wanted to have plenty of time to explore the city, book experiences, and also not have every day jam-packed to the point where I would feel exhausted.
I planned so many activities that I ended up feeling like two weeks was a perfect amount of time for me. It’s also a great place to use as a base if you’re looking to explore other areas of Tuscany. If you’ve never been to Florence, I would absolutely consider allocating more time here than you might have planned. I did SO much in the time I was there, and I’ve listed it all below.
How I Got Here
- I booked a train from Desenzano del Garda/Sirmione to Firenze Santa Maria Novella with a stop in Verona Porta Nuova to change trains. My first train ended up being delayed so much that I was going to miss my connection in Verona. I ended up paying over 100 euro for a taxi to the Verona airport. It ended up being easier for me to do this quickly than to figure out the next train option and be late to meet my Airbnb host. I was able to make it to Verona in time for the second train. Had the original plan worked out, it would have been 28 minutes from Desenzano to Verona and then 1 hour and 47 minutes from Verona to Firenze.
- Timing details: My train was supposed to leave Desenzano at 8:49 am and arrive in Verona at 9:17 am. There was a 20 minute connection, then the next train left Verona at 9:37 am and arrived in Florence at 11:24 am.
- ***I bought my train ticket on the Trainline app 3 days before***
Where I Stayed
- 2 bedroom apartment in Santa Croce
What I Did
- Bistecca Experience
- Organic Cooking Class in the Tuscan Hills
- Bike Tour in Lucca (day trip)
- Cooking Class at Pasta Class Florence
- Truffle Hunting
- Cooking Class in the countryside with Luca and Lorenzo
- Sidecar Tour and wine tasting in Chianti
Sorrento
Why I Chose This Location
I stayed in Sorrento in 2021 and fell in LOVE with it. The first time I arrived here, I just felt this inexplicable connection to the city along with immediate relaxation.
Sorrento is a great spot to have as a home base as you explore the peninsula and Amalfi Coast. It’s usually less expensive, doesn’t require you to hike 1,000 steps to your hotel or Airbnb, and has more shopping and dining. You can easily take a ferry or private boat on a day trip to Positano, Amalfi, or Capri. You can also take a day trip to Pompeii, which is easily accessible by train.
How I Got Here
- I booked a fast train from Firenze Santa Maria Novella to Napoli Centrale (2 hours and 59 minutes). From there, I would change trains to the Campania Express from Napoli Garibaldi to Sorrento. Unfortunately, my first train was severely delayed due to weather, so I missed my train to Sorrento and ended up getting a ride to Sorrento from Naples with an American couple I met on the train.
- Timing details: My train left Firenze Santa Maria Novella at 11:14 am and was supposed to arrive at Napoli Centrale at 2:13 pm. It actually arrived at 4:13 pm. I arrived by car in Sorrento around 5:30 pm. The Campania Express that I had planned to take would have left Napoli Garibaldi at 3:37 pm and arrive in Sorrento at 4:46 pm.
- ***I bought my ticket to Naples on the Trainline app a week before. The Campania Express ticket can be bought here.***
Where I Stayed
- Corso38 - a boutique B&B
- Sorrento Flats - - a boutique B&B
What I Did
Amalfi
Why I Chose This Location
I briefly visited Amalfi one afternoon in 2021 when I was staying in Sorrento and had wanted to go back. It’s such a cute, picturesque town on the water and I managed to find an incredible Airbnb with a view. I decided it would be the perfect location for two nights on the Amalfi Coast.
How I Got Here
- I was originally going to take the ferry from Sorrento to Amalfi, but the weather was looking a little bad. Apparently, if the water is rough, the ferries can cancel at any time, so I didn’t want to rely on that. I was not willing to take the bus (I get nauseous easily) and I also had trouble finding a private driver. Luckily, my B&B host, Luigi, found a friend of his who wasn’t working and was willing to drive me.
- Timing details: The ride took an hour and a half from Sorrento to Amalfi. We left at 8:30 am and arrived at 10:00 am.
- ***A typical ride from Sorrento to Amalfi will cost 150€***
- When I left Amalfi, I took a fast ferry to Salerno (20 minutes), where I got a fast train to Rome (3 hours). I booked the ferry the night before (you must buy your ticket at the ferry office in Amalfi) and bought the train ticket on the Trainline app while waiting for the ferry. There were very few tickets left, so I recommend booking a little more in advance if you can.
Where I Stayed
- Private room at an Airbnb with an amazing view of the marina
What I Did
While most people will likely not have an entire month to spend in Italy, or will want to see as many places in the time that they have, this itinerary can still be used for ideas on what to do in each of the places I stayed.
If you do happen to have more time on your travels, I highly suggest spending more time than you might have planned in some of the destinations you want to visit. This allows you the ability to rest, see more of the details of the city, and connect with the locals, especially those in the neighborhood where you’re staying. Get a cappuccino in the morning from the same cafe and you’ll feel like you’re part of the community; this is one of my favorite things to do.
I always love hearing from those of you who end up taking my suggestions, so if you book any of the experiences or locations above, feel free to send me a message on Instagram or an email and tell me how you enjoyed it.
If you’re looking for help with planning your next trip, I offer consulting, so feel free to reach out to me. Have an incredible trip!! You’re going to love Italy.
