Generally speaking, Havana is a very safe city. The heavy police presence is there to prevent tourists from being hassled by hustlers and solicited by sex workers, while the thought-police (or Communist Defense League), are the regime’s eyes and ears and are there to ensure that there are no liberal tendencies incubating.
Keep your belongings in sight at all times, but petty theft isn't really a huge issue – just don't be flashy with cash or valuables wherever you go.
The tourist influx has seen a rise in street crime, especially in Old Havana.
Always keep your valuables locked in your room and be mindful of the usual tricks aimed at separating you from your wallet.
Try to avoid taking pictures around uniformed guards or military installations.
Avoid and be firm with hustlers, known locally as jiniteros (jockeys), who will try to lure unassuming tourists into Havana’s seedy underbelly. If you are approached, politely say no and continue walking away. A friendly smile will help let them know you aren't being rude, and will hopefully avoid further confrontation.
Should you fall ill, you could do a lot worse than Havana.
Cuba's medical services are excellent, and most treatment is provided free to foreigners at local clinics, hospitals, and hotels; although getting the drugs you need may be another matter entirely.
Waiting is something that Cubans excel at: waiting for buses that never come, waiting for rations, waiting to see what will happen now that Fidel has finally gone.
Everything from ordering a meal, to waiting in line at a museum, to paying your bill at a hotel, requires patience – in spades. Get used to it, and learn to live the slow life while traveling here.
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