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In Italy hitchhiking is a bit less common than in France or Germany but it's very well possible and doable.
You can get a free map of a whole Italy at almost every petrol station (autogrill). This map has all petrol stations marked in the map.
Roads are often not laid out for bicyclists and pedestrians which makes it harder to walk towards or find good spots. Always make sure to stay safe, and do some research before heading out to hitch.
Even though most Italians do not speak English (or at least there is such a common assumption) they seem to understand a lot of it. Same goes for Spanish.
"Hitchhiking" is autostop in Italian. Just say autostop and the name of your your destination or show your thumb, otherwise Italians would think you are asking the directions as Italy has a lot of tourists. For detailed information on speaking italian check the Italian phrasebook on hitchwiki.
To avoid misunderstandings for both of the above, it's a very good idea to write a sign.
Also, try writing the name of a sensibly chosen city some 2-300km in the right direction. For example, if you're heading from Milano to Napoli, few people will be going that far in one stretch. So try writing first Firenze, then Roma and finally Napoli. You might get there in just those three stops.
The northern part of Italy is quite safe but take care in the south of Italy. When pitching a tent in the wild make very sure to stay out of sight.
Hitchhiking (Il)legal? - Hitchhiking on the autostrada is not legal (there are big signs saying no autostop at motorway on-ramps) but it is unclear even to Italians whether this extends to petrol stations (area servizio) on the autostrada. Most likely, this sign originally was meant to stop people from walking on motorways. An American that encountered police (polizia who drives light blue cars) at an area servizio on the motorway was simply warned not to walk on the autostrada and to stay at the station until finding a ride. Once you are on the motorway, don't put your thumb out, not even at the exits of service stations - then the police will warn you. Try rather asking drivers while they refill their cars.
If you're on a petrol station it's a good idea to stay on friendly terms with the staff. When starting, it's probably a good idea to find a spot before drivers encounter the no autostop sign; once you have passage onto the autostrada it is fairly simple to skip from one service area to the next until you arrive at your destination. It's less likely that you will encounter problems if you're not Italian -- and, if you speak Italian, don't reveal this to police (or the armed forces carabinieri).
Hitching in Italy
Take the motorway A23 (in the eastern part of Italy) to Austria (don't try to hitchhike through Switzerland, it's very difficult). Follow the A23 to Villach and Salzburg to get through the Alps very easy. On that way, you will also find a lot of people heading to Hungary, Slovakia and Slovenia. You can also try to hitch A22 to Bozen, Innsbruck over the Brennero but it's quite difficult to find a hitch from A4 to the A22 except when it is holiday time. Also, don't go via Milano, it's really difficult to get out of the ring because almost everybody drives into Milano and very few stop at service areas located nearby.
There are a lot of tourists from Austria and Germany, especially in summertime. The new European car plates start with a letter on the left side of the plate, representing the country. Most Austrian (A on a plate) and German (D on a plate) are on the way to the sea or on their way back from holidays, so if you want to go North or South, try to find Germans or Austrians (usually, they speak better English than the Italians, too). wikipedia:Italy trash:Italy
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