Å tip is probably one of the safest cities in Macedonia, and definitely much safer than all the major cities in the western and central part. Violent crime and murders are almost non-existent, and property crimes are very rare. Foreigners are welcomed and looked upon as a curiosity as Å tip is not advertised or developed as a tourist destination, despite having a lot to offer.
There are several night clubs in Å tip, and they are all much safer than any western counterpart no metal detectors anywhere. Keeping a low profile is recommended as not to tempt the local macho mentality. Aggressive courting of girls is not recommended as this can be seen as encroachment and cause physical conflict.
The Roma Gypsy population of Å tip is mostly living far bellow the overall poverty level, and although their shanty towns spread around several areas of the city, mostly in the north are very picturesque and exotic for the tourist to behold, avoid giving them gifts or money, as that will make you a target for more panhandling and possibly a non-violent property crime. Do not be fooled by the looks of the Roma children beggars, for most of them that is their full-time job, and no one is dying of hunger or cold in Å tip.
The police is sometimes helpful if approached politely, but beware that the socialist heritage where the police was very brutal and was mostly used to keep an eye on the population, instead of maintaining law and order, is still very much alive. Ask a younger person for directions, as most youngster speak passable English, and only deal with the police when you have to, taking good care not to offend them in any way.
As pretty much anywhere else, do not accept offers from strangers; do not enter in business deals with unknown people, even if the offer is most tempting; do not go to secluded or dark places at night or abandoned places during the day, and exercise good judgement that you would in other poor countries like Mexico or Central America.
Do not be alarmed if glasses are shattered by being slammed on the ground as this is a cultural thing, especially when one male individual is intoxicated and there is live music. This practice is quite common for males of all ages, and is the same in all the surrounding countries like Greece, Bulgaria, Serbia and Albania.
Don't carry too much cash on you and do not flash/show it there is no need, there are plenty of 24/7 ATMs around the city. Try to dress like the locals. Too much differentiation might attract unwanted attention, which, while usually harmless, can be very annoying at the end. Lock your valuable in the hotel safe or hide them well. Keep your electronics and cameras in bags for most of the time while taking picture/videos around.
At the end, exercise a common sense that you would exercise in rural Alabama or West Virginia, for example, and you will be fine and have a great time!
