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You can sleep in Barcola - a big park on the coast about 5 km far from city center. You can reach Barcola with a bus C from the railway station or with a tram from Obedram (tram station not far from center). You can also sleep in a tent there: in the morning there are many people coming to swim, but nobody pays attention to the tent.
If it's getting late and you didn't find a place for the night, the train station is also a good option. Just find a quiet spot, between the others that already did, and you'll get a rather quiet sleep for the night; Until 6:20, when the guard came and woke everybody up, I wasn't bothered at all.
WARNING: DO NOT SLEEP AT BARCOLA! OR IF YOU REALLY HAVE TO: DO NOT PUT A TENT THERE!
The wild camping is strictly prohibited in Italy. The penalty for that is 200EUR and Barcola is patrolled by Carabinieri every morning. One I had to sleep there (it was too late to get anywhere else). Although I didn't put a tent and made my place look like early beachgoer, in the morning I was woken up by the police. Fortunately, managed to get only with admonishment, mainly because I didn't have a tent.
If you want to sleep near the see, go near to Miamare castle. There are some flat concrete spots, where you can safely sleep. Keep close to the road so you won't be visible from the road. And be warned: the Carabinieri outpost right above you! Thus I would not recommend putting a tent, but I found it quite comfortable to sleep just on the inflated mattress there it during the summer.
The other option are hills above Trieste. Take the bus 2 and go near to Obelisco on the top. You can also take a bus 38, but you'll have to walk a little up from the last stop. There is a tap with drinkable water near the Obelisco. Go to the Obelisco, you can put a tent behind trees near the Obelisco. Also you may take dirt road that does not go up and you will find some places near the road (with nice view on the bay).
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