As Bosco suggests it’s easier than it looks at first glance, just like France. Best recommendation is just to plan a flight and go do it to see how it works out. Otherwise it’s a bit of a glass half empty or half full. Sounds like yours is half empty. I concur with most of the other comments.
BTW, I have made quite a lot of trips to Italy since Covid raised its head. Interestingly, Italy relaxed its restrictions quite rapidly and flying there was possible when much of the rest of Europe was still pretty much in lockdown. This past June I did LSZK-LIPB-LIPU-LIKO-LIQS-PG20-LIQQ-LIRJ-LIKO-LIPN-LIPB-LSZK over a 9 day period and it was simply a gas. Weather was mostly good, but the airfields were all easy (except perhaps Siena LIQS which was rather slow on the PPR and cost €180 per aircraft for PPR & the fire truck).
Also, last time I was in Losinj on a weekend, the parking was full to overflowing, about 50:50 Italian reg vs Germany/Austria. The Italians were mostly certified, in the C172/182 and Cirrus category. Croatia is a good destination for Italians, which may be why we don’t see so many out and about nationally. 
Thanks for all the replies everyone. I think for VFR flying anywhere in Europe, you need a native guide sitting in the right seat for the first few hours. After that it seems less terrifying, at least that has been my experience here in France.
Last thing, as soon as you contact Milano Radar after Leaving France, be prepared to be asked for ALL your estimates :lol:.
An American friend of mine was part of a group ferrying some small planes from Scotland to Africa a few years back, all VFR. His tales of interacting with Italian ATC are lengthy and entertaining!
For me, for now anyway – not having a plane to fly – this is just a thought exercise. Scary and fascinating in about equal parts.
Another point, airfields like LIDO Ozzano and LIQQ Serristori are as nice as you’ll find anywhere in Europe. Ozzano has fuel, a restaurant, pool, and no fees. LIQQ Serristori has fuel, a restaurant, a hotel, pool, and also no fees.
@Steve6443 its not just an Italian thing you can train of a non EASA certified in France too.
Don’t get the point why flying VFR in Italy seems to be so difficult… In fact, it isn’t, see also @boscomantico replies.
Personally, I do like flying in Italy. First of all, the country offers a lot from historic and scenic places, up to mountains, coasts and beaches. Second, Italian people are often very friendly and welcoming, even with language barriers. Third, there are many airfields to fly to, including a lot of smaller airfields without landing fees. Fourth, the weather in Italy is often stable for VFR flying. Fifth, Italian ATC is actually pretty straightforward, it’s just FIS that often feels chaotic. There are only two issues that cause me some pain in Italy: Expensive landing and/or handling fees at most of the controlled airports (incl. bureaucratic invoices), and the big and low Alpha airspaces across the country, especially the Milan TMA close to the Alps. But there is also no Italian rule without exception. If you are flying high and already in contact with real ATC (not FIS), they may let you fly VFR through airspace A on some occasions at higher altitudes. I’ve been accepted two times through the Milan class A TMA, but I’ve never been accepted through the class C TMA of Zurich in Switzerland. Makes sense? Not really, but it gives a good idea that habits are different across each country. And this takes me to the final point:
A European pilot should be flexible and be able to quickly adapt to national routines. Never think or expect that everything abroad works out the same way as in your own country. Sometimes, I still hear some German pilots calling non-existing ground stations at unattended/uncontrolled airfields abroad, British pilots still requesting for “basic service” in mainland Europe or even (American) pilots requesting “flight following” in Europe. These pilots seem to be unprepared to fly abroad. But being “flexible” doesn’t mean you need to know everything upfront. In my opinion, it’s just a state of mind. Do a careful preparation with apps like Skydemon, Windy, Rocketroute etc. Read the AIP, listen carefully during the trip how local pilots perform radio calls, talk with locals on-site, and last but not least, read reports from other pilots (like here on EuroGA). The rest comes on its own.
You hit the nail on the head, Frans. Flying abroad VFR is all about that in my experience. Nothing to worry about…
I enjoy your YT-channel very much btw. 
+1
Hi, came across this thread.
I am looking at doing a transit from Locarno (LSZL) to Cannes (LFMD) over easter. Weather permitting, I would love to do that VFR and enjoy some of the views.
Ideally I would like to go pretty much straight south to the coast near Genoa (I flew there IFR in the past) and follow the coast VFR to Cannes (also done that before).
What I find confusing, looking at the map, is to find a route from north/lake Maggiore to Genoa that avoids all the restricted zone (R-101, R-102) and all the airspace. I don’t mind doing zigzag, but somewhat bothered if I have to cross all the north of Italy at 1000’ then zoom up to 5000’ to get over the mountain.
Any thought of the best way to do that? Below seems to more or less work, except for the fact R101 would get be around below 1500’. can you get higher transit on R101 or it’s a no-no?
Is it better to go east and get transit via class D of Turin?
thanks for any advice from the locals…
101 and 102 are not that much of a factor. They start at 1500 AGL, so you can do 2000 MSL (and you can’t do more than 2500 MSL anyway, due to the TMA).
Still, I would rather fly via Lugano and from there to SRN. Much easier, because if you first route down Lake Maggiore that puts Malpensa CTR in your path, as in your routing above, which you then need to circumnavigate carefully.
But yes, either way, you later have to
climb a couple thousand feet to cross the Ligurian Apennine.
Lugano SRN makes a lot of sense!
Will do that (if weather permit)
Thanks a lot!
