Cuba has the lowest crime rate in the Western Hemisphere. Even in neighborhoods that you would avoid in other major cities (such as much of Centro Havana) you are unlikely to suffer any incidents of violent crime. Incidents, which do happen, are generally tied into a more personal encounter with ‘dubious characters’.
Petty crime is more of a concern and a bag left unattended in a major city may well be swiped. Pick-pocketing does happen in certain locations, especially in certain busy discothèques or in public artcraft markets, even on busy streets, although it is relatively rare and should be preventable with a certain degree of caution and lack of ostentation. Take care of items such as handbags, cameras, neck chains and other items that can be snatched away.
General hassling is pretty prevalent at least in Havana and Santiago de Cuba in major tourism spots. Hustlers are called jiniteros/as literally jockeys and while they can be an annoyance are generally pretty good natured and non-threatening once you accept their existence and learn to politely but firmly decline their offers of cigars/’friends’/special paladares etc.
Begging does exist in certain spots but again is pretty minimal and non-invasive.
This really is a question of your own attitude. Some woman are OK with the flattery and the attention, which is omnipresent, others find it threatening and unpleasant. You need to bear in mind that a Cuban guy is simply programmed to whistle and shout compliments at a pretty woman walking down the street. Anything else would be considered an insult.
Having said that as in any country, especially in major cities you need to use your female instinct. Don’t go down dark streets at night, the same streets you wouldn’t go in your own hometown. Take a taxi when you go out at night and ask the taxi driver to wait until you close the door of your home behind you. Smaller towns like Trinidad or Vinales are safe at night time for female travelers.
Cuba is normally safe as long as you are reasonably careful about what you eat and drink. The common travel-related diseases, such as dysentery and hepatitis, are acquired by the consumption of contaminated food and water. While Cuba has a relatively low incidence of HIV any visitors should take obvious precautions if engaging in intimate relations on the island.
Mosquito born illnesses are not a significant concern on most of Cuba although you should be aware when there is a periodic outbreak of dengue. Sand flies can be a serious irritant on certain beaches but this is to be expected as the price of paradise!
Tap water in Cuba is not considered as reasonably safe to drink. Most Cuban households will boil water before drinking and foreigners should follow this procedure unless you have good quality purification filters.
Since May 2010, Cuba has made it obligatory for all foreign visitors to show proof of their medical insurance when entering the country. Basically all foreign policies are accepted and any review is cursory if any at all. As when traveling in any country having valid travel insurance is a sensible and important step.
Cuba has its own state owned insurance company (ASISTUR), which will (if you prefer) provide travel insurance for around US$ 2.50 per day for non-Americans (US$ 8 per day for Americans).
In the event that you need medical treatment you will need to pay following your treatment and make a claim back from your insurance company. ASISTUR is the entity, which will deal with the paperwork. Typically treatment is relatively cheap (a simple consultation and prescription is likely to be under US$ 50), although prolonged hospitalization will obviously increase costs exponentially (a week treatment in intensive care with all of the associated care, tests might run to US$ 5,000).
The Cuban government has established a for-profit medical system for foreigners called SERVIMED, which is entirely separate from the free, not-for-profit system that takes care of Cuban citizens. There are more than 40 SERVIMED facilities throughout the country including in all of the major tourism centers. The major clinic for foreigners in Havana is the Cira Garcia one in Miramar.
In the event of an accident or other emergency foreigners may be taken to the nearest accident and emergency center, which may be at a Cuban state hospital. Conditions here at least aesthetically are likely to be below expectations for many foreigners although the standard of care is typically very good from the doctors. Once a foreign patient can be moved typically he will be transferred to a SERVIMED clinic such as Cira Garcia in Havana, which is set up to deal with foreigners.
There are special pharmacies for foreigners also run by the SERVIMED system. These have limited supplies however and should not be relied on especially outside of Havana for specialist medicines or prescription medicines (although typically they will have alternatives). As in many countries a fully stocked medical kit should be packed as part of your travel luggage.
Regular tourists who plan to spend up to two months in Cuba do not need visas. Instead you get a tarjeta de turista (tourist card) valid for 30 days, which is possible to extend for another 30 days once you are in Cuba. Canadians get a special deal and can stay for up to 90 days.
Tourist cards for travelers arriving from the Americas can typically be purchased at the airport of departure although will generally be provided or sold ahead of time by the travel agency or airline office for US$ 15-20). For travelers from Europe typically departure airports are not allowed to sell tourist card and you must have a valid tourist card before arriving at the airport. These are available at the relevant Cuban consulate although again for a small additional fee can generally be ordered from travel agencies.
Once in Cuba tourist card extensions or replacements can be arranged at the relevant immigration office for US$ 25. This process can be something of an ordeal if you dislike bureaucracy but is relatively straightforward (if time consuming).
You cannot leave Cuba without your tourist card so should take not to lose it. If you overstay your visa this will present a serious issue when leaving the country and care should be taken not to do so.
On your tourist card you need to fill in where you are staying. If you are staying in multiple locations you need simply put the first one. Cuban unwritten rules say you have to book a hotel for the first night. This is not an actual regulation and it is legal to stay in a licensed casa particular. Many people just find it simply to put the name of Hotel down. It is rare that immigration officials will ask for evidence of a confirmed/paid for reservation although it makes sense to have a print out of any confirmation that you have even if this is only a non-confirmed, non-paid for quotation.
Travelers are allowed to bring in personal belongings including personal jewellery, camera and video camera a mobile telephone, one personal computer, sporting equipment, wheel chair for the disabled, personal portable devices that allow to extract or introduce information into personal computers, such as flash memory, MP3, MP4, IPOD, electronic book, and the like.
It is prohibited to bring in global positioning systems, satellite telephones or other communications equipment such as listening devices. Electrical items (including toasters/irons etc.) are also not permitted.
Fresh food is not allowed although enforcement is somewhat sporadic on this.
Other items on the no-no list include narcotics, pornography, explosives etc.
NO NEED TO FILL OUT THE CUSTOMS DECLARATION FOR PASSENGERS if they just bring with them those items considered to be personal belongings or an amount of cash not exceeding $ 5000, 00 USD or its equivalent in other currencies; or other appliances.
Strictly speaking the maximum value of any gifts brought to Cuba must be less than US$ 50. The key to this is not to overtly flout the rule bringing in say 50 baseball caps or expensive electronic equipment. Items that are classified as gifts (over US$) will be subject to a 100% tax on their cost price.
For details, refer to the FAQ page of the Cuban Customs www.aduana.co.cu, which clarifies the details.
Internet access in Cuba is notoriously expensive and slow although has improved recently as ETECSA has set up an increasing number of Telepuntos that offers reasonable internet access for CUC$ 6 per hour. The national system requires that you buy a scratch card with user name / password which you then enter into the terminal. The national nature of the system means that you can use any unused part of the time as any other telepunto location.
In Havana a number of the more upmarket hotels offer Wi-Fi access for CUC$ 6-8 per hour. This is an incredibly popular service since it allows you to use your Blackberry / IPAD / lap top and not be restricted to a telepunto computer. The quality of service varies and will almost be slower than you expect. The best hotels for this are the Parque Central and Panorama.
Outside Havana options are more limited and even though most major hotels will have their own internet cafes the speed of access is often enough to make you dream of your old dial up connection back home!
ETECSA, the national phone company, has roaming agreements with most major international carriers (excluding US carriers) so theoretically your phone should work in Cuba. It is worth checking rates before you go since horror stories abound of people who have used their cell phones to access data packages as well as voice and received huge roaming bills back home! As a general rule roaming is great for texts, extremely expensive for voice calls and variable for data access.
Letters and postcards have a funny way of arriving from Cuba at unexpected moments and are worth sending just for the surprise when the day comes that it arrives. This may be in a few weeks or a few months but typically will make it. Notionally regular mail should take a month to Europe or North America. Stamps are available both in local currency and in convertible currency. Given that the postcards are only US 65c to all countries it is worth spending the extra cash for the boost in reliability. For important documents you should use the DHL office which has branches in all the major cities.
Skype does work in Cuba from one of limited number of locations, which offer wi-fi service. Periodically attempts have been made to block this however it does seem to function reasonably well from hotel lobbies such as the Parque Central or the Panorama in Havana.
The big advantage of a Cuban cell phone is that making calls within Cuba is much cheaper than with a roaming international phone. Bear in mind this still does not mean that it is cheap (see below)! You are able to rent a Cubacel SIM card from many of the major airports in Cuba, which have an ETECSA office. Alternatively you should look for the nearest ETECSA office in the city. You will need to show your passport and you will need to pay CUC 3 per day for this service. In order for your phone to be able to use the Cubacel SIM card it will need to be unlocked and to operate on the 900mhz frequency. You will need to simply top up your phone through purchasing pay as you go Cuban phone cards which generally retail at CUC 10 or CUC 20 per card.
*Cubacel is the cuban mobile phone division of ETECSA (the national Cuban state owned telecoms company)