|Motorways:||A1, A4, A7, A8, A9|
The Milano metropolitan area is very large and the road network complex. If you are dropped at a petrol station on the outskirts of Milano, it will probably prove faster to take public transportation across the city and hitchhike from the other side, than to try to get a lift around the city.
From the city center, take metro 2 (the green line) towards Cologno or Gessate. Get out at Gobba.
East towards Verona
If you want to go east towards Verona on the (A4), try the following. At the end of the platform of Gobba, right where you get out of the train, there begins a bridge over the motorway leading to an extra train which only goes to a hospital. It costs 1.20€. After you get out at the hospital, follow the stream of people and go up the first steps you see (round ones). Look for a high place – from there you can see a petrol station. It is best is to ask someone to show you the best way down to the petrol station.
An alternative and easier option is to take metro 2 (the green line) to Cologno Nord. It doesn't really matter which exit you leave the station by, as long as you are walking north. Follow the road for about 5 or 10 minutes until you get to the beginning of the bridge over the motorway. Rather than actually crossing the bridge, you turn right, off the road, and walk along the raised grassy area beside the motorway. After 4 or 5 minutes you will have reached a gas station. Now (feb.2014) there is a fence but if you walk towards the electric tower you'll find a broken part of the fence where you can pass to the other side and reach the gas station.
Southeast towards Bologna
Walk for around 10 minutes from Porto di Mare metro station to the petrol station (also Agip) on the other side of the motorway. Look on the city map in metro stations how to walk there exactly - very simple.
Option 2 : Another easier option to reach Bologna and South Italy is to take the Green Line to Cascina Gobba, after that get out from the station and you should see many orange buses( Atm), so go left and you will find a gate, go in and walk until you will arrive to a roundabout and from there you can see the gas station in the highway which you reach easily in two minutes. The advantages of this spot compared to the "Porto di Mare" spot is that this is on the highway, Porto di Mare it's not. So it should work fine! Update 8/2014 They are renovating the gas station! Probably it will be opened in spring 2015 on time for the Expo!
South towards Genova
Take the metro to the station Famagosta. When you exit to the street, to the east you will see a bridge. This is the A7 motorway. You then have to walk a couple of minutes north parallel with the bridge to where the motorway begins. There is a traffic light and a petrol station. It is best to stand a couple of meters north of the traffic light, next to the petrol station entrance, with a sign. Cars are going slowly (or stopping at the traffic light) and there is enough room for a car to stop easily.
West towards Torino
At the end of Via Antonio Sant'Ellia (metro station QT8 on the red line) close to the park Monte Stella, there is a big slipway to the full motorway interchange between A8 and A4. So it is possible to hitch to west, north and east from there. Stand on the curb before the slipway splits with a sign. There is a street lamp nearby, so it is possible to hitch at night. N.B. occassionally there is street prostitution on the other side of the road close to stadium San Carlo.
Another good place where you can catch more westwards traffic is at metro stop Molino Dorino. There is a roundabout which splits the ramps and car park driveways. Stand at the traffic light close to Via Fratelli Rizardi with a sign. Because of the traffic light, cars need stop longer before ramping onto the motorway tangenziale ovest A50, so you have more chance to be seen and longer time for the driver to think.
There is a petrol station on the A8, before the junction where the A9 branches off, leading towards Switzerland. You can reach it by taking a local train to the community of Rho (S5 or S6 should go there, 5 stops, 2-3 Euros but there are no barriers et5) and then taking a bus towards Lainate. Just ask around at the bar in the Rho train station, they should be able to tell you what bus to take (a blue one, not the orange ones!) The bus should cost around 1,55 Euros. Get off at the stop Via Pagliera or Via Alessandro Manzoni, and walk towards the little roundabout between Via Giacomo Puccini, Via Scarlati and Via Gaetano Donizetti. This is an industrial area, just walk to the end of Via Gaetano Donizetti, you will reach the petrol station, southwards (there is a turnstile in the fence). On the petrol station, find the sottopassagio/underground walkway which will take you to the other side. From there, it should be easy to get a hitch on the A8 or A9 northwards, towards Lago Maggiore, Lago di Como, Switzerland.
The hospitality exchange community is one of the biggest in Italy, you should not have problems finding a host on Couchsurfing etc.
If you hitch at Monte Stella, there are plenty of long benches in the park and a public water tap nearby. It's a good place to stay on a summer night.
Parco Nord (tramway 31 or 4, taking from yellow subway zara or maciachini) can be a nice spot to camp. Big enough to hide, lots of tap water. Parco Lambro may also be a good place for free camping. However, there is risk of theft in either park. All other parks inside the city (Giardini di Porta Venezia, Parco Sempione, Parco Solari) are closed during the night.
Eating in Milano
The are two places Milano where you can have free food. Both give food for homeless, poor people and are called "Pane Quotidiano" (It means "daily bread") They usually give some bread, pasta, vegetables and sweets every day without asking you money or papers from 7:00 to 11:00. One is located in Viale Monza 335 you can arrive easily there with the Red Metro Line in Villa San Giovanni the other one is located in Viale Toscana 28 you can arrive there with the bus 90. You can recognize it easily because you can see lots of people waiting there. (Note: Do not abuse these places, they are for those who really need it! Prinoblog, talk 13:16, 2 June 2014 (CEST))
Busking in Milano
Milan has a very welcoming policy for street performances. They may now perform in the designated squares and streets every day of the week from 09.00 to midnight. There is an official website "Strada Aperta" where you can book the place where you would like to perform, usually you can find many performers in the centre from Corso Vittorio Emanuele to Piazza Castello.