Visa: travelling from Italy to Cuba through Russia
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Assuming you’re transiting Russia from Italy, you need a transit visa http://www.russianconsulate.info/transit_visas.html and a tourist visa for Cuba. The latter are not available on entry, are valid for 30 days for a single entry, and can be extended for a further month. Some airlines include the Cuba visa when you book, or you can obtain one via a travel agency or the local Cuban consulate https://www.worldtravelguide.net/guides/caribbean/cuba/passport-visa/ On entry in Cuba you must be able to show proof of confirmed return flight and booked accommodation (note: it is illegal to stay in an unregistered casa), and you should have adequate travel insurance.
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Source: stackoverflow.com
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