Recently, many people have asked me how I planned my 4 cities in 4 days trip around Northern Italy. I used to be the kind of person who travelled to one city and spent the whole trip in the one city – but lately, my holidays are rarely limited to one city. Thing is, some cities/towns really don’t need more than one day to explore completely, and would be a wasted trip if one stayed there for a number of days.

I do admit, however, that Venice and Florence definitely warrant a return trip for a couple of days! I feel like it was a bit rushed and would love to return for a more relaxed visit.

In this post, i’ll share a few tips for deciding where to go and how to plan a multi-city trip, like mine!

Choose a region that you want to travel to

Stick to a specific area; let’s say, the North of Italy only, or the South of Spain. It just isn’t practical to travel from the North to the South of a country within one trip – you’ll just end up heavily travelling within your travels! I decided to fly to Milan, as it was extremely cheap (£25 return), and then looked at surrounding cities and went forward from there.

Do some research on the proximity of cities/towns in that region

If cities in that region are more than 2 hours away, then consider a different geographical region. You want to be sure to balance travel with sight-seeing and relaxing.

Fly to and from the city that is the cheapest

When you decide which cities you would like to visit, check flights to all of them, and fly to the cheapest one! You also don’t have to fly to and from the same city; if cheaper, you can fly to one city and fly back home from another! It’s possible!

Make sure your hotel is in the middle of the areas you would like to visit

Choose a hotel that is as close to the centre of your travels as possible. Even though we flew into Milan, we decided to stay in Bologna, as it gave us great links to the other locations, and is a great location itself. By doing this, you save travelling time, and tickets would also be cheaper, as the distance is shorter.

Pre-book train/coach tickets online

Prior to flying out, I booked tickets online using TrainLine and GoEuro. Set yourself a rough schedule for which cities you would like to travel to and on what day of your holiday. Pre-booking tickets online is smart for a number of reasons; firstly, it saves time as you already have your printed tickets and all you need to do is print them out and jump on the train on the day! Secondly, it saves you from being overcharged due to communication barriers that you may face at the station ticket office. You also have the option to search for the cheapest price online dependent on time and method of travel.

I found that certain times of travel were cheaper than others; this is something that the person in the ticket office won’t have the time (or patience) to nit-pick over with you. I also found that sometimes, travelling by coach was 1/3 of the price of train travel, but only a tiny but slower (GoEuro is amazing for this comparison). Bologna to Florence by train was 35 mins but by coach it was over 2 hours – so we went for the train option.

Online, you always have the option of selecting English, and it just makes it easier to purchase online than a panicked purchase at the ticket office.

Join walking tours

Try to get to your destination early in the morning, and join a morning walking tours. Considering you don’t have much time in the day, a walking tour can really give you a breadth of information in a short time, and you don’t waste time getting lost. It also helps as you will most likely meet other people (locals/tourists), and can ask for specific locations you may wish to visit.

Join walking tours

Do your research on things to see, and places to visit. Use guide books, travel blogs, YouTube vlogs and ask around! I used a few guide books that helped with highlighting the main attractions that I needed to see, and also gave some other suggestions if time permitted. This was definitely so helpful! I simply starred the locations in Google Maps and went along the path visiting one by one, and bumping into other sights along the way.


Sometimes, the desire to see as much as one can, can take away from the enjoyment and the moment. Be sure to have some moments of slow pace, sit down, take in the environment, grab a gelato and sit on a bench and soak in the scenes. It would be unfortunate to have spent 4 days seeing 4 cities, without even recognising the main sights or smells, or even without talking to a local.

Do you have any other useful tips for city hopping?

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