The longest and one of the best rides I ever did was across the mountains of Cilento Italy with an English (more or less) speaking, Italian guide named Vincenzo.
It was from village to village, so I couldn't say the actual mileage, but it was literally up and down steep, rocky and beautiful remote areas with wild boar, deer, wolves, wild cattle (territorial and aggressive buggers, especially the bulls).
Fascinating people and really rough riding. I loved it.
Took a bit of getting used to, but that is what travel is all about.
Did you know that the rural Italian culture has absolutely no qualms with drinking anytime of the day? That took some practice and I still can't drink Grappa, but the locals do...for lunch....after all the wine.
There were times, we had to push ol Vincenzo back upright in the saddle once he started getting horizontal on us....fractured refrains of "O solo mio" drifting down the mountainside....you may think I'm kidding....but not...anyway I'm getting off subject.
The horses were local bred Italian horses that were used to the altitude and terrain. Nothing fancy, but good at their jobs.
The tack was a mix of English, Italian and trekking and crap.
Another interesting thing I noticed was that much of their gear is tattered and ancient. Why throw something out if you can use it one more day...or another second....? It just added an extra thrill in the event one of us might fall to our deaths down some rocky craig should a piece of equipment give way....
Look at the halters in the photo as an example. lol!
We were in a small group of 4 with a guide.
Not a great picture, but take a look.
I'm with Vincenzo and you can see the bay of Cilento in the background.
Edit 1 - I understand my first link was dead, so I deleted it.
Edit 2 - Well...despite my best efforts, I can't get the #$!@ picture to up load...sorry folks : /
Edit 3- to BB - Wow, that's some date!