How to plan an Italian trip

Planning an Italian trip was more difficult than any of my other trips and much worse than I expected. And although I don’t normally use travel agents, this was one occasion where I thought that it would have saved me a lot of stress to use one. I had to draw up a to-do list, divide it into sub-lists and then work on the details. To be honest, it began feeling more like a chore and at some point I even wondered if it was worth the hassle.

Venice How to plan an Italian trip


This is what I had to do:

  1. Decide on the dates. We were going on a Mediterranean cruise leaving from Venice. These dates were fixed therefore the rest of the itinerary had to fit around that – and my children’s school holidays.
  2. Book flights –this was the easy part. Once we had decided on our dates, I did a search on Travelstart and found that Emirates had the best deal as they were having a sale. We then proceeded to book the flights although we did have to adjust the return date by a day or two in order to get a better deal.
  3. Work out a broad itinerary. Italy has tons to offer and with the limited number of days we had available, we had to decide which cities we would be including in our trip. We decided to stay in Rome, Venice and Florence and included Pisa as a day trip from Florence.
    Leaning Tower of Pisa

    Leaning Tower of Pisa

  4. Book hotels in each city. This was the worst part because I had to take several factors into account such as child-friendliness, proximity to transport hubs and attractions, price, cancellation options as well as TripAdvisor reviews. My timing appeared to coincide with a busy tourist season as the weather was great, so availability was limited especially in Venice and Florence. The hotels my friends recommended were full. kept on sending me messages to say that the cities I was travelling to were 60% (increased to 70% then 80%) booked on my dates. While there were still hotels to choose from, when you have to multiply the Euro prices by 15 and still find something decent, it doesn’t leave one with that many options. And although I normally prefer 4 or 5 stars, the prices were around R3000 a night for a 3-star hotel in Italy. In South Africa, comparable hotels would be around R1200. In the end, I had to make some decisions. I booked a night at the Rome Airport Hilton and the rest on and – and they didn’t turn out too bad.
  5. Apply for Schengen visas. One would think that it would make more sense to have ones visas approved then book accommodation but in order to apply for a Schengen visa, one had to have confirmed accommodation first. At least our travel insurance was covered by this. Read about the convoluted Schengen visa process here.
  6. Ascertain the best way to travel between the cities and book the transport connections. We decided to book the first two legs then buy the rest of the train tickets at the railway stations on the day we were travelling – as we wouldn’t have saved by buying them earlier.
  7. Work out the finer details of the itinerary. I used TripAdvisor to research the top activities and attractions in each city as well as the best method of booking for them. Then I had to book the ones that were necessary to book beforehand – such as Galleria degli Uffizi in Florence and the Vatican.
Rome How to plan an Italian trip


Other things I had to do

  • Inform the bank that we would be travelling and using our bank cards overseas so that they didn’t suspect fraud and put a stop on them.
  • Put my newspaper subscription on hold
  • Change the contact numbers on my home security company’s account.
  • Pack for 4 people for 3 weeks in the smallest amount of luggage possible

So, planning my Italian trip was a long and time-consuming process but in retrospect it was worth it as we came back with a treasure trove of memories. Although, it would have been wonderful to have a little more free time to unwind in between a jam-packed schedule. Then, we wouldn’t have been so exhausted by the end of our trip. For more about my Italian trip, click here.

For cheap flights to Italy, click here.






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Zaakira Asvat

Slmz, hope you’re well.

My husband and I have booked to go to Italy in March, and since I’m not a well travelled person, I don’t know where to start planning. We aren’t doing it through an agent either. Would it be possible for you to send me some rough guidelines of your itinerary, as we are doing Rome, Florence,Pisa & Venice? Thank you


    Wslm. Sure, I will email you.

      Zaakira Asvat

      Thank you so much for your willingness to help me. I really appreciate it. 🙂


We leaving for Italy on Friday,thanks to your articles I feel a bit at ease especially with traveling with a 7 year old and 3 year old.


    I’m glad you find them helpful Sumayyah. Let me know if you need any information that I haven’t covered. And have a wonderful holiday!

Razena |

I read this before I started making arrangements for my trip later this year in shaa Allah. I really appreciated the advice.


    Thanks Razena. I hope it helps. If you need more advice/information, feel free to email me or inbox me.


love your blog. Can’t wait to read more


    Thank you so much Fadeela. I am glad you’re enjoying it. Happy travelling!

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