Pornographic material of any kind is considered immoral (therefore, illegal) by Cuban authorities and will be confiscated immediately at the border. This rule comes from pre-internet time, so it was aimed at detecting printed magazines and VHS cassettes in travelers’ luggage. Standard airport screenings can’t detect digital content of this kind, but if for any reason your laptop or other devices are inspected and contain porn, you’ll be in for a long, awkward interrogation.
Cuban law makes every effort to protect you from libelous criticism of the Revolution (in Cuba, “Revolution” refers to the current system and/or government), and Customs officers will help you to dispose of any unreliable books and magazines you may have brought to the country. It’s unlikely that Customs officers will spend time scrutinizing English-language books; these controls normally target Spanish-language books with titles and covers are easily identifiable as “contrary to national interests,” generally written by dissident authors who are already on the government’s blacklist. In other words, no one will care about something esoteric like Milton Friedman’s Capitalism and Freedom, but beware of negative titles including “Cuba” or “Revolution.” If a book has a potentially suspicious or controversial cover, wrap it in newspaper or magazine sheets to disguise it and make it look like something of little value.
Wireless technology is not welcome. Don’t try to bring hardware to set up any kind of network, including routers and switchers. Also prohibited are wireless microphones, any kind of radio equipment (radars, walkie-talkies, etc.), and equipment for satellite communication.
Although no one is going to examine if a smartphone’s location feature is activated and communicating with a satellite, that’s all the GPS Customs will tolerate. Professional GPSs (Global Positioning Systems) cannot be imported into the country without a permit from Cuba’s National Office for Hydrography and Geodesics). This regulation comes from a pre-smartphone era, when commercial use of GPS was not as extended, but the prohibition remains in place for dedicated devices and modules.
In an austere country like Cuba, the convergence of more than one of the same item may be disconcerting and, sometimes, costly or illegal. For instance, bringing a single laptop as a personal item is free, but a second one requires paying an import fee for a second one ($250, or $100 for a mini-laptop). Similar limitations apply to other devices. By law, bring with no more than:
A copy of the regulation (Resolution No. 30 of 2014) and a longer list of maximum amounts is available in Spanish here.