Find that toilet!
Kuressaare is lovely place but it get's it share of tourists who drink too much beer and decide to relieve themself somewhere outside. If you are caught doing that you will spend a night in jail and pay significant fines for your stupidity.
(disclaimer: this hasn't happened to me!)
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Nap in the middle of the street
This is quite peaceful town, although I happened to see one real "strange" person. Kuressaare does not have traffic lights, instead there are plenty of pedestrian crossings. One sunny day on the busy street - right in the middle - one man in his 30s or 40s perhaps thought that street is a perfect place to lie down and take a nap little bit, ignoring all the traffic.
You may though that this person in my picture is knocked down by car. Wrong! He is just sleeping. 8-/
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