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Violent crime is extremely rare, but vehicle break-ins and pickpocketing are not uncommon. Key West is home to a large homeless population. Use the same level of common sense you would use elsewhere in the USA Pay attention to the weather.
The Keys are a narrow band of islands that offer little protection from tropical storms. In the past storms have generated waves with enough strength to demolish bridges and topple freight trains and engines sitting on tracks. The locals seem immune to these dangers: If it is suggested you go back to the mainland, do so immediately. There is only one highway out and it can become clogged quickly.
The Overseas Highway can and will be closed for a period should a car or truck accident occur.
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