Annemasse LFLI to Venice Lido LIPZ VFR

Wow, unless you are willing to fly a huge detour, this is a challenging flight. Keep slightly north and you will be in the mountains all the time, keep slightly south and you will be in an airspace mess (Milan class A TMA and various airport CTRs) all the time. If you are good mountain pilot and if the weather is excellent, you could fly (approximately):

Annemasse, Montreux, Martigny, Sion, Raron, Simplon Pass, Domodossola, Locarno, Belaggio, Lovere, ELTAR, PIRWO, Padova, Porto di Malamicco, Lido

If that is too challenging for you, then consider going all the way south and fly:

Annemasse, Grenoble, Gap, Cannes, Genova, Parma, Porto di Malamocco, Lido.

You did not mention what you intend to fly.
Annemasse Raron Locarno Vicenza/VOR Padova
(a few VRPs) Lido.
That’s how i would fly it and normally do it across the Alps. In a TB20 (ceiling 18000ft).
Needs a good engine / sufficient ceiling, oxygene and some radio work. Never been a problem, so far.
In CH just stay out of Zurich airspace and thinks are straightforward. Locarno can be overly precise, but manageable.

I’ve done as Bos said, with minor detours (Matterhorn, that sort of stuff) Great trip. Provided you’re well ahead of the aeroplane it’s not particularly challenging as long as you have great weather. That’s the biggie. It’s a morning gig for sure. And defo psz3. The view is sensational.

I should add I did it with my son who’s also a pilot which made life much simpler.

@DC10, I had a quick look as well since this route would be going thru my playground
And I came up with about the same route Boscomantico is suggesting, see below. It’s all out of CAS and the highest col is the Simplon with 6’578ft.
As you can see, there are some TMZs and flying below the CTR of Venice approaching destination. One could fly the route talking only to the departure/destination fields, but I would recommend calling Venice approaching their airspace. One Italian specialty is asking for your intended route and estimates. And one of the SD strength is the Pilot Log page giving one all the needed info

I would go to Albertville and then follow the valley until Gap, passing by Grenoble. From Gap the is a valley rising up to VEVAR, which you have to cross at FL100 at least, and from then, suddenly, everything is flat (almost) until Venezia, routing via ASTOR – ULCOR – IBLUN – SUXIL – NISIL and them the VRP for LIPV (Chioggia and Porto di Malamocco) I’ve done this Gap-Venezia route a few times, VFR, flying high (natural air con for summer), and in radio contact always. It keeps you out of the Milan class A TMA. This routing is similar to the one proposed by Boscomantico, but saves some miles since your cross the Alps instead of going south up to the Mediterranean. The trickiest leg could be Gap – VEVAR, since you follow the valley (it’s wide) to much higher ground and you need a minimum ceiling, but in good weather (morning if summer) it should pose no problem

Flying in Italy expect to be requested frequently to report your next waypoints and ETA/ETE to at least the next one. Apart from that, very standard.

I would advise going south by Cannes and then Genova, as you will be able to do it high but below FL100. If you go through the Alps, apart from going to the simplon pass, there will be low ground clearance and you will then have to descend below the italian A-Class that lies ove the north part. That’s a detour for sure.
Otherwise, you can reach Gap LFNA then go north through the valley of Durance to Briancon, then the col de Montgenevre to Italy via val di Susa. That’s a “below FL100” route with some ground clearance, but:

• in Summer time, this is a “convective wind place” so check the wind, and avoid if predominant is 20+kn. anyway it may be bumpy, except if flown before 10am.
• Once reaching Torino, you will have to fly around cities and airports and 1000ft agl. until Periggia/Brescia (I din’t remeber exactely where the east border of the A class is).