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Usually, the most any traveler in Havana will have to worry about is pickpockets. Always have your hand on your bags, latches secured and keep only small amounts of money handy. The majority of the city's residents are very poor, and if you are clearly a tourist or are conspicuously displaying watches or jewelry, you are tempting a crime. If a thief confronts you directly, do not resist, as they may have a concealed weapon or partners standing nearby. If your passport is stolen, you must notify local police as well as the government in your home country. There are few situations where you will need a passport and it is better to leave it in a secure location. Just carry a copy
Due to the nature of Cuba’s government, there are a few more ominous safety issues that travelers should be aware of. Boating accidents among tourists are common, because the waters near Havana are choppy and tricky to maneuver through, and it is very difficult to get proper boat repairs in Cuba. Another serious warning: in 2003, three Cubans were executed by the government on charges of attempting to hijack airplanes and boats and use them to escape from Cuba. Such an event is certainly uncommon, but it would not be impossible for tourists to be put in danger by an attempted hijacking. Consider this risk before deciding to travel in Havana.
It is against the law in Cuba to take photographs of military, police, airport or other transportation facilities, although enforcement of this law is understandably erratic. If you do not wish to draw unpleasant government attention to yourself, avoid taking photographs in any of these locations!
Cuba generally has the reputation as a safe location for tourists and there are usually police on every block. However. in the past several years, increasing economic and social hardships on the Cuban people have made it more dangerous to walk the streets late at night so it is advised that you not walk alone and know exactly where you are going. Be aware of crowds as violence can erupt very quickly and the police may respond immediately or they may not -- motives in Cuba vary sitiuation to situation especially since pay for government jobs is dropping.
Any discussion of safety in Cuba should also include the safety of Cubans that you meet. Increased sanctions and a campaign against prostitution have contributed to greater vigilance from police for Cubans fraternizing with tourists. Tourists have less to be concerned about than Cubans and sometimes you will read that tourists are "teflon" or something similar -- this is true. However police will often detain or even arrest Cubans who are consorting with tourists on the street or in cafes especially around Malecon. Understand that the police in Havana are not from Havana and do not live in the city, so they have very different motivations than the Habeneros. If you care about the fate of the people you meet:
Getting arrested in Cuba is no trivial matter and the fines for Cubans might amount to 2-6 months pay for an infraction - or jail.