Your guide to seeing the best of Italy! Sites, landmarks, routes, prices, travel tips, and more! 

Venice

Pisa

Naples

Milan

Genoa

Rome

Amalfi Coast

Florence

Ultimate Italy 3 Week Itinerary: Italian dream summer 

If you’ve ever wanted to explore Italy, this guide is for you! I took this route a couple of years ago on my second time in Europe, and it was one of my favorite trips to date! I started at the north end of Italy and took trains to get from each city; I used the train line website and it was a super easy journey the whole way! I booked two one way flights (one from Venice and one from Naples) so that I could easily start in one end of the country and end in the other end of the country.

The one thing I loved about Italy compared to any other country I’ve visited is that every city feel so unique that it could be its own country; and although everything looked so different, together it all made up Italy and I find it beautiful that it makes the country so diverse, unique, and beautiful at the same time.

Before I get into the itinerary, I’m gong to get into a few logistics that will make everything run smoothly for your journey.

I flew into Venice, and then took trains to each subsequent city. I eventually flew home from Naples; I did this by booking two separate one way flights. To buy my train tickets, I would either buy them the night before via trainline though either the website or the app, or I would get to the train stations a few minutes early and purchase them there. You can check train timings from trainline; I would ultimately recommend you buy your tickets at least one day in advance, as they tend to be cheaper 1-2 days before departure, sometimes by up to 50%. I typically only bought my tickets at the station if I wasn’t entirely sure what time I wanted to train to the next destination.

You can honestly stay in any type of accommodation whether it be a hostel, airbnb, or hotel. When I went I stayed in hotels, and just booked many different reservations.

You could definitely play it by ear if you wanted to and book you accommodation either a few days or the night before, but I personally planned it all out ahead of time. I wanted to have the clarity of when I would be in each city ad I also liked the idea of knowing for sure that I always had somewhere booked to stay the night, just in case for some reason places filled up. I would recommend researching each destination before you go and figure out exactly what you want to see, so that you can estimate how much time you’ll want in each place

I flew into Venice because it was the most northeastern part of Italy that I wanted to visit. I arrived into the city of Venice by taking a bus from the airport and then a water taxi into the city; they’re pretty cool as they look like subways or boats such as they have stops all along the way.

From Venice, I took trains to each subsequent city that I visited. I stayed in Venice for one day, and I found it to be more than enough to explore the city and take in the rustic most unique streets. I suggested visiting Venice for 2 days here, solely depending on the type of traveler you are; if you like to take a slower approach and visit lots of shops along the way and the smaller details of a city, stay for at least two days. If you’re like me and just love to see the city and take in the atmosphere, one day will be more than enough for you as well.

Compared to the other cities, Venice is probably he one that I find the most unique. It is really small and perfect to aimlessly wander around, as you will likely cover the whole city in a day without even realizing. It gives off this really relaxing and happy vibe which is the perfect start to your upcoming journey!

Milan is a very elegant city, and almost gives off the bible that it has a hint of Paris. It’s definitely one of the bigger cities in Italy, and is definitely worth checking out.

The first thing you should do is check out the Duomo cathedral, it is located in the north central part of the city, and is absolutely breathtaking; it is one of the biggest cathedrals I’ve seen and is so stunning to look at. I would also recommend waking up super early to see it before the crowds emerge and crowd the area. If you would like to go inside, the interior is stunning and definitely worth a visit. What’s cool about this particular duomo as well is that you can go upstairs to the roof, where you get the most spectacular aerial views of Milan. The architecture on the roof is also amazing and makes for great pictures!

If you like Starbucks, the Starbucks reserve is definitely also worth checking out. It is one of the few Starbucks reserves in the whole world, and is absolutely massive. It has a selection of exclusive food and drinks you can get at other starbucks, as well as an exclusive set of merchandise. It also has a massive coffee grinder and roaster that stretches two stories up and is a sight in itself!

Another cute place in Milan to check out is Navigli, the canal of Milan. It stretches along the east coast of the city, and is lined with little boats and colorful buildings. There are also many little vendors along the sides, and restaurants/cafes where you can sit and have a drink!

In the evening, I would also recommend checking out the aperol spritz bar; it looks over the duomo and has gorgeous views of the square below. Aperol spritzes are such a classic Italian drink, and I personally think this bar is one of the most touristy things you can experience.

Another experience you can do while in Milan is visit lake como for the day. It is about a 40 minute train ride, and only costs €2.50! It is very easy to get to as you just take the milan centrale station, which brings you right into the heart of lake como. From the lake, you can take a boat and tour around, or walk around, and stop at one of the Italian restaurants or cafes along the way! Lake Como is stunning and honestly looks like it was straight out of a fairy tale.

Recommended stay: 2 days, or 3 if visiting Lake Como

Genoa is not that well heard of, but I would definitely recommend giving it a visit as well. I stayed here for two nights, and it was a great choice! There is not as much to see in Genoa as Milan, so it is a nice place to visit to give yourself a bit fo a rest in between visiting big cities. If you walk along the coast, there is a line of colorful houses that lines the shore, thatvlooks alot similar to the famous CinqueTerre. The beach is really nice and not as busy as other popular Italian beaches, which makes a perfect beach day! Along the main road near the beach, it is lined with palm trees and fancy tiling that completely will make you feel like you’re in Monte Carlo! There are also so many Gelato shop that are perfect for hot sunny days.

I’m sure you’ve heard of Florence, as it is one of the most famous cities in Italy, located in the heart of Tuscany! I stated in Florence for three nights, which gave me four days in this city; I found it to be plenty of time and would have been happy with one or two days here, however, I know so many people who love florence and could spend weeks here, so the timing is really up to you!

I found that the whole city felt like you were in a castle, as the narrow streets were lined with cobblestone and the walls of the buildings on each side were tall and appeared to have tops like a castle. There were also so many horse pulled carriages, that really added to the medieval vibes. I definitely also would not recommend trying to drive here or even number, because the roads were so small and there were so many people around, making it nearly impossible and taking so long to get even the shortest distance by car.

The train station is very close to the city centre, and you can easily find a place to stay that is a 5-10 minute walk; in terms of luggage, there were not that many stairs here, making it easy to wheel a suitcase.

The city is built along a river, with lots of bridges along the way, connecting the city to the other side. On the north side of the river, there si a massive set of stairs that leads to the top of a hill, where you can find the Michaelangelo Lookout point; I found this point to be my favorite part of Florence, because the view is absolutely stunning; especially if you go in the evening where the city is lit up by the glowing sun.

When I stayed in Florence, I spent one of the days and took a day trip to Pisa, to see the leaning tower of Pisa, and be a tourist of course. Once in Pisa, there was not much else to see, so I would say it is perfect for a 4-5 hour activity.

Rome is next up on our adventure, and is a great city to mark the halfway point! We are also going to take a train here (surprise!) and we will be arriving right in the heart of the city. I think Rome was my favorite Italian city, because of the architecture and all the famous landmarks to see while there.

I was the most excited to visit this fountain, mainly because of the turquoise blue waters I had seen in photos. The fountain in person did not disappoint at all, and definitely exceeded my expectations. There are normally ques that can be quite long if you want to go right to the foot of the fountain, so it is a good idea to visit the fountain early in the morning to beat the crowds and the heat. And don’t forget to make a wish while you’re there!

This is of course one of the things that absolutely screams Rome; I’m sure most people around the world associate it with the entirety of Italy, as it is so massive and so famous and just iconic all around. If you want,  you can go inside the colosseum and really get a taste of history; just like the trevi fountain, I would definitely recommend going super early as I went mid day and the line had a wait of over 3 hours.

The spanish steps are just around the trevi fountain  and also worth checking out! You can climb to the top and get great views of the city, and they’re just really pretty in general. Careful not to sit down though, as security will soon have you off the steps!

Ultimate Italy 3 Week Itinerary: Italian dream summer

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