Which cities Should You Visit in Italy? The Best 10 Day Guide From Milan To Positano

If you’re planning on going to Italy, it’s hard to decide which main cities to visit and in which order. This is the perfect 10 day guide to visit Milan, Lake Como, Florence, Rome, and the Amalfi Coast for first timers. This is an overall guide on how long to stay in each main city when visiting Italy and includes any bordering towns and cities you can see during your stay.

Questions before planning:

Is 10 days enough to see all of Italy?
While it’s not enough time to see all of the cities in Italy, it’s a good amount of time to visit the more popular sites. If you’re wanting to visit more places, consider extending the trip to at least 14 days to add one or two more cities.

What is the best time to visit?
Summer is the most popular time to visit but this comes with lots of tourists, delayed train and ferry schedules and long lines for food reservations. I recommend going off-season which would be between September-November as this is the perfect time to beat the crowds but still enjoy your time by the beach before the weather gets cold.

What is the best form of transportation to get around Italy? Is it accessible with a baby?
The best way to get around is the bus or train. If you’re city hopping, pre-book all your tickets to avoid the lines, booking the wrong times and having to validate your ticket. Be sure to read my list of the most important apps you should download before your trip to Italy or any European country. If you book online, you do NOT have to validate the ticket saving you one extra step. The tram system is not child friendly as all the stations are underground but each city is extremely walkable and you can always call an Uber. At certain times and locations (the streets are very narrow and some are blocked off just for pedestrians), most Ubers don’t come so I recommend standing next to a taxi sign when ordering an Uber in the evening so they can come directly to you.

The Itinerary

Milan and Lake Como

Start with 2 days in Milan or Lake Como. We based our stayin in Milan and took one full day in Lake Como spending the time in Varenna and Bellagio and the next day exploring Milan. Milan is more of a metropolitan city and can be seen in one day so if this is something you aren’t interested in, then spend two days in Lake Como. The Train from Milan to Varenna was the easiest route to take and I booked the tickets through Trainline but you can also take an uber or taxi which will be a bit more pricey. When spending the time in Como, limit it to two towns so you can spend enough time exploring each place. If you plan on visiting any villas, book everything in advance because the lines take too long and you will waste most of the day waiting to get in. The ferry tickets weren’t hard to get either when we were town hopping in lake Como but the last one leaves around 7pm. We did Milan-Varenna-Bellaggio-back to Varenna and back to Milan.
Where to stay in Milan: Torre Galfa Milano Luxury Apartments

Florence

From Milan, make your way to Florence, or Firenze and you can ideally see this in about 1.5 days if you take an early train ride but make it 2 if you’re traveling with children to get a bit of a break. Milan was our favorite city and I would love to go back and explore more of Tuscany alone. This town is small, quiet and extremely walkable. The streets are narrow so if you’re walking with a stroller, you will have to share the streets with the cars but it doesn’t get very busy since most people walk everywhere. The main thing I recommend doing here is making a reservation for a Florentine Steak at Trattoria Dall’Oste.
Where to stay in Florence: Corte Guelfa

Rome and Vatican City

From Florence, take a train to Rome and spend 3 days here. It seems like a lot but compared to Florence, Rome is very big and not as easy to get around since the main attractions are not very close to eachother. If traveling with kids, space each sightseeing place out and don’t try to cram everything into 1-2 days you will not be able to enjoy it. This is one of the most popular cities for tourists so expect lots of crowds. Don’t forget to visit the Vatican and spend one day here but book everything well in advance so you don’t miss out on any of the famous museums.
Where to stay in Rome: Hotel Dorica

Amalfi and Positano

Ending your trip in Positano, I recommend basing your stay in Sorrento for 3 days. I cannot say enough good things about the beautiful town of Sorrento and how it’s the perfect location from Amalfi, Positano, Capri and any other small towns you’d like to visit around the area. The ferry station is walking distance and easy to get to and from but be sure to check the ferry schedule well in advance as they only go out every hour and the last one leaves at 6pm from Positano and Amalfi. If you miss the last one, you will have to come back via Uber or Taxi which can be difficult to find.
Where to stay in Sorrento: Maison Blu