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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) or here. This map has all petrol stations marked in the map. It is generally fairly easy to get rides on petrol stations, especially if it is a guy and a girl.
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. Italians do not generally stop on the road.
As in any foreign country, learning some of language is recommended, aside from Italian and local dialects, French is spoken in some areas of Piedmont and Aosta, German in South Tyrol. A handful of words from a local dialect may make drivers loosen up. Spanish is easy for Italians to understand.
"Hitchhiking" is autostop or passaggio in Italian. Just say faccio autostop or cerco un passaggio 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. In areas like Puglia people are so friendly that you can just basically ask if you could crash at their place if you need a place to sleep.
Hitchhiking (Il)legal? - Hitchhiking on the autostrada is not legal (there are big signs saying no autostop at motorway on-ramps) and it extends to petrol stations (area servizio) on the autostrada. Fine is 21 euro (so you need to find excuse for not having that money, poor traveler, somebody stole it etc.). Most of the times police just ignores you or say that you must go further from exit. If you happen to gt kicked out of a petrol station by the police they'll tell you to go to the nearest train station and take the train. If there's no way around it you can simply dodge the fare as the Italians themselves say that "nobody gives a shit about the law in Italy." The conductors usually can't articulate anything beyond "Money" and "Ticket" in English, so just tell them "No money, no ticket" and they'll let you be.
Easier it is just to ask from people while they refill their cars. Hitching on the petrol stations is generally fairly easy. If petrol stations has exit to normal road, then police asks you to leave. And when it happens that you are on the motorway, don't put your thumb out.
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, but it is still possible hitchhike while you have no autostop behind you; 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).
Strada Statale(national road) - Because of petrol station problem in Italy (see above), you can try hitchhiking on Strada Statale - SS. It takes little bit more time, but you meet more local people and you can see beautiful nature, they can drive you extra kilometers, so you could arrive to destination or invite you to have a lunch with their family.
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 Bolzano, 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).
Another option is stay on the A4 and ask trucks on the petrol stations. Many trucks go to Austria, Slovakia, Poland and more north through Slovenia to tank diesel there because there is cheaper diesel and on the roads there aren't so many hills so it saves fuel.
Ferries between Italy - Greece
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