Our Italian Holiday Itinerary!

It’s been MONTHS since we returned from our once-in-a-lifetime family holiday to Italy. I have been meaning to blog about it since July 2019 and it’s now March 2020!

I think the reason for the delay was that I returned with almost 4 000 photos of our trip and I needed to make my way through all of them, then edit, resize, export, upload and allocate to all the various destinations I want to write about. There are A LOT!

Unfortunately, now that a few months have passed, I may not have all the details, but ultimately I want to post the pics of each place we visited plus some of the story of our journey for my own records – and if it helps you to plan your own trip to Italy then that would be awesome!!

So, let’s begin!

Our journey to Italy began 9 months before we stepped on a plane, when one spontaneous Saturday evening we booked ourselves flights! I can’t quite recall what happened. There may have been some wine involved, but although it was super spontaneous for us, it wasn’t really. We have been talking about a trip to visit friends of our who have a home in Italy for YEARS. I was lucky enough to visit these friends back in 2009 when I was pregnant with our second, but my husband had not had the opportunity and for years I had said to him I want to take him there and experience everything with him. Once our second baby was born and the expenses of kids mounted, the dream died… or took a back seat for a very long time![/caption]

Each year we would see these friends on their annual visit to Cape Town and promise that we would visit in the future… as South Africans it felt a very long way off!

Finally, fueled by the fact that these friends would be living at their Italian home permanently for a year before deciding whether to sell or not, we decided to finally take advantage of our Vitality flight discount on Emirates and press BOOK. A few moments after we did we both looked at each other in disbelief. This type of reckless behaviour was very out of character for us, but now there was no turning back!!!

I can honestly say booking those tickets was the best thing for us in many ways. A few months afterwards I was offered a short term contract with a set salary and it was the most obvious answer to our concerns about covering all the costs. So I took the job. 18 months later I’m still at the same company, loving working with a great team, learning a lot and making money that has gone beyond paying for our Italian holiday and now covers High School expenses, a new (second hand) car and much more! I’m so grateful! I wonder if we hadn’t had the Italian holiday looming whether I would have said yes?

Once we had a flight booked we started saving in earnest. Other people might be more motivated to save BEFORE booking a trip. I learnt that I’m not like that. I’m far more motivated when there is actually a flight number and accommodation booking to pay for! This meant we were much more disciplined than usual when it came to eating out, entertainment, Christmas presents and extras. We were all very focussed on having enough rands to get at least a few euros. Our kids also became very focussed on saving their pocket money to be able to spend it in Italy rather.

Having a holiday to look forward to also really lifted our spirits and helped us to get through some really long, hard months. We booked our flights in September to fly out a few days before the June/ July holidays started. It was 9 months of excitement and planning that I loved! I actually find the pre-holiday planning one of my favourite aspects of a trip and I loved that ours was quite extended. It also meant that not going away during the Dec or April school holidays was made easier knowing we had something really great to look forward to!

This trip was also the very first time both our kids joined us on an international trip and seeing their excitement at applying for passports and visas and anticipating their first international flight was really lovely! I SO enjoyed seeing them reading up about Italy, practicing the language on the Duolingo app and watching videos about what to expect. I love travelling, but I adore it even more when seeing the experience through the eyes of my kids. They LOVED the process – from planning to flying to arriving to exploring. It was all magical for me – and for them! In fact, the travel bug definitely bit during this trip and I’m so thrilled to take them adventuring again in the future. They both lapped up every opportunity, meeting locals, taking in the scenery, understanding the culture and eating ALL the Italian food. It’s basically heaven for a family of foodies like us!

On a cold, wet Wednesday we finally found ourselves at the airport with all our luggage! Excitement levels were super high… until we realised that we didn’t have our kids birth certificates with us! An hour of sheer panic ensued as we frantically tried to solve this. A few panicked prayers and a couple of guardian angels and we finally found ourselves through passport control and ready to take flight on the first leg of our flight.

Emirates makes flying with kids a breeze and ours LOVED their own entertainment screen and the free reign and zero time restriction we permitted during the flight! They were also gifted a great activity pack which helped to pass the time. As I mentioned this was their first time on an international flight and they were a breeze! I can honestly recommend waiting to take kids overseas until they are a manageable age. Ours were 9 and 12. Aside from some frustrations with learning how to sleep while sitting upright, we didn’t have any problems.

After our 9 hour direct flight from Cape Town, we landed in Dubai International Airport at 6am which was 4am for our body clocks! Not ideal when trying to get kids to manoeuver through a huge airport with their respective bags, fortunately the excitement of the experience fuelled them on and they were rewarded with their first experience of a first world train (to be honest it was probably their first experience of a train!)

I recall flying through Dubai airport on my previous trip to Italy and I found it vastly overwhelming as a newly pregnant woman on my own. Emblazoned in my mind was the sheer variety of shops and people from all over the world. It was mind-blowing for me and I was so excited to share that with my family this time around. We only had four hours in transit before our next flight so we weren’t able to exit the airport and explore the city of Dubai (maybe next time!) but we made up for that by finding ourselves some seats where at least 2 of us could put our feet up and keep an eye on the luggage while 2 of us would go wandering and window shopping! Let’s just say our SA budget didn’t stretch very far here!

Finally, after another 6 hour flight, we touched down on European soil. We flew into Milan Malpensa airport (there are 3 in Milan alone!) as this was the cheapest route for us from Dubai and then made our way to luggage collection (my kids realising the value of the British passport when I was able to walk straight through the automatic gates and they were left in a very long line with their dad!)

A while later we finally found our way to the shuttle collection point for our car hire company, B-rent. After some confusion and a phone call we confirmed we were in the right place and waited for the shuttle along with a few other travellers.

On arrival at their tiny little prefab office in a parking lot on the outskirts of the airport industrial area I was a bit dubious, but they were organised and efficient, we just had to wait a while for everyone else who had arrived on our shuttle to get their bookings processed. By this stage the 28 hours of travel was affecting some in our party!

What I can say about renting a car in Italy is to be aware of the extra car insurance that these car rental companies often try to trick you into! We were a bit thrown initially when they asked to hold R8 000 on our credit card until I did some quick Googling and realised that our initial online booking already had sufficient cover for our needs and we didn’t need to take out any further cover.

During our planning we weighed up whether it would be worth having a car hire for the whole trip or just a portion. We knew we definitely needed it when coming and going from our “home” base with our friends as their place is up in the mountains so we opted to hire a 4 seat vehicle with a decent boot for the entire duration of our trip. (NB boot space is important especially on your trip to and from the airport. Ours was quite tight with a few bags being placed on laps!) Looking at the costs of the train tickets and adding in the stress of getting our luggage on and off PLUS figuring out the schedules etc we thought it would be easier to have our own vehicle. Ultimately it was the best decision for us despite some frustrations, let’s just say driving on the motorways in Italy is interesting!

Firstly you have to be fairly confident driving on the opposite side of the road, then there is usually no shoulder on the road with the left hand lane up against a mountain and the right hand lane a sheer drop off or a tunnel wall. Add in an endless stream of huge trucks that drive over the speed limit right next to you and you have got a recipe for stress. We promised each other that anything said in the car would be forgotten as soon as we stepped out! Other things to take note when driving in Italy is that it’s best to book your city parking in advance or at least plan where you want to park in advance. Driving in the cities is stressful enough! In Florence we found a parking area to park in where we wanted to explore from and paid by the hour but then when we wanted to find somewhere to park overnight it became more complicated and expensive! There are also many roads that are part of the Zona a traffico limitato (ZTL) which is a restricted traffic area. There are 200 schemes in various big cities that are enforced with cameras. The idea of these zones is that they help protect historic city centres from excessive traffic, which would otherwise make the city less attractive. We got caught out once when we drove down one road with the sign, fortunately we made a quick exit! Find out more here: Urban Access Regulations

In Rome the driving was intense! We relied heavily on Google Maps and would have never managed without it, but the roads were still stressful. Very congested with lots of scooters and many one ways! Fortunately our Airbnb came with free parking which I can HIGHLY recommend as something to factor in when booking accommodation in any big Italian city. Our Airbnb in Trastevere was fairly central and we could walk almost everywhere so that meant we could park our car and leave it there for the entire duration of our stay. The only other time we needed to find parking was on our way out of the city when we visited the Vatican and I managed to find a parking garage nearby where we could book in advance and pay by the hour. When we headed to the Cinque Terre we didn’t take our hire car and rather had our friends drop us off at their local train station where we caught the train and avoided the parking costs. In Venice we parked at the main parking garage which I also booked online in advance and it was really easy and uncomplicated as the only road into Venice leads you straight there!



Over the next few weeks I hope to be sharing a blog post about each destination… but this might take a while! In the meantime here is our itinerary that you can use to plan your own trip. As I add in blog posts I’ll link to them from here too so you can easily access info about the destination you are most keen to explore on your own Italian holiday!


Our Italian Holiday Itinerary

Day 1 – Fly CT – DBX – MLP

Day 2 – Arrive Milan Malpensa Airport and drive to Cisigliana village

Day 3 – Unwind at Podero dell’Angelo in Cisigliana

Day 4 – Explore Pisa, Lucca and visit local winery

Day 5 – Visit local villages including Fivizzano and Lerici for a swim in the Med

Day 6 – Firenze!

Day 7 – Quick visit to the Superdry outlet at Barberino Designer Outlet Village followed by a visit to Querceto di Castellina winery in Chianti, Tuscany

Day 8 – Explore the towns of Tuscany – San Gimignano, Montalcino, Montepulciano, Pienza including a visit to Castello Tricerchi

Day 9 – Roma: Trastevere and the historical centre

Day 10 – Roma: Colosseum and Forum

Day 11 – Roma: The Vatican plus road trip back to Cisigliana with stop off at a local winery.

Day 12 – Relax at the pool!

Day 13 – Explore local villages – Fosdinova and Sarzana

Day 14 – Arrive in the Cinque Terre

Day 15 – Monterosso Al Mare: Beach and Wine

Day 16 – Riomaggiore and Manarola

Day 17 – Rest and relax at Cisigliana with a quick visit to Castel del Piano winery

Day 18 – Drive to Venice from Cisigliana. Stop off to visit Coffele Winery.

Day 19 – Explore the islands of Venice – Murano, Burano, Lido

Day 20 – Enjoy a walking tour of Venice with The Roman Guy

Day 21 – Drive from Venice to Milan Malpensa airport and fly home!

Kathryn Rossiter

Kathryn is a South African lifestyle blogger and mom of 2 who has been blogging daily for over 9 years! She writes about travel, health, beauty, fashion, decor and family... but not food (unless it's food she's eaten made by someone else) as she is a hopeless cook. She only wakes up early for 2 things... a red-eye flight to somewhere exotic and early morning game drives. She has just finished an extensive home renovation and would prefer to never see another box again. She's never met a chocolate or glass of bubbles that she didn't like!

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