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Traveling to Cuba can be one of those life transforming  experiences.  Here we present some practical information to help make that a  reality.  If you are not subject to US law, skip this next  section.
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For US Citizens or Residents - US Law

To go down legally, even if you are not a US citizen but a resident, however temporary, you need a Treasury license, which you obtain from OFAC, Treasury's Office of Foreign Assets Control.  

If you are  Cuban-American or married to one, you can go down once a year under a "general  license" for humanitarian reasons (grave illness in the family, etc) and you  only need to notify them via a form, but you do not need to get a license from  them before leaving.  If you are a "U.S. and foreign government official traveling on official business, including a representative of international  organizations of which the U.S. is a member; or a journalist regularly employed by a news reporting organization," you also qualify for this "general license."  

Otherwise you need to get a license from OFAC to avoid being at risk for large  fines.  Check out http://travel.state.gov/cuba.html

There is a surprising number of categories which qualify for a treasury license: full time students, musicians, dancers, anyone going down for  professional reasons, journalists, and so on. Treasury tends to encourage group travel and frowns on individual researchers, which makes you wonder who is the collectivist here....

In all the years of the travel restrictions, very  few people have been prosecuted. The Office of
Foreign Assets Control in the  Treasury Department recently said there have been only 16 criminal prosecutions for nine violations since 1983. Nine of the cases have been in the past three  years.

Many folks have gone down openly without a license. The penalties  on record are stiff: $750,000 fine and up to 10 years in the pen, but until failry recently fines have been minimal.

There has been a recent disturbing trend in '97 and continuing into '98: high fines for persons unfortunate enough to be caught without a  license, typically when they go through customs with Cuban products they are  bringing back, but sometimes through more mysterious means.   Fines, which in '97 averaged around $1,000, are now going up to $6,000 and $7,000 and in one case to $30,000!  Traveler, beware!  The situation has gotten to the point where people are getting together to create a legal defense  organization to defend the right to travel.

Note that Cuban Americans and Americans who are married to Cubans  have a general humanitarian license to go down once a year in case of a grave  problem such as a serious illness in the family. This license, unlike other  licenses, is not one the recipient actually needs to apply for and have physically in hand, though they are responsible for notifying Treasury of their  departure through a Treasury form.

Others who apply for a license they need to receive in their hands are subject to resource scarcities within Treasury, the body that grants  licenses. Be warned that licenses may not come or may come too late for travel  if you don't give yourself plenty of lead time and put in for a date ahead of the one you need.  

Also note a recent disturbing trend of denying more of these  licenses than has been the case in the past, possibly due to pressure from the  Miami Cubans, who are incensed when Americans travel to Cuba.

We do not recommend going through the Bahamas. US Customs there  have been known to confiscate religious objects. When you travel via Cancun, you pass customs in the US. Via Canada, you pass US customs in Canada, but they are  more civilized. 

Do not bring cigars back, they are very illegal... and if you've been bad and have asked the Cubans and the Mexicans not to stamp your passport (bribing the Mexicans $20), then be sure to tell the truth if the customs agent asks you where you've been. It is a worse sin (a felony) to lie to a federal officer than to go to Cuba without a licence.

Excess baggage: the  regulations on this vary from airline to airline. Generally, anything over 44 pounds (20 kg) is considered excess.  Cubana is among the strictest, and will  even refuse to take on excess bags or charge $7 a pound.  Mexicana is among the most generous, charging only $1 a pound.

Cuban Law, Cuban Visas, & Security

Tourist visas for anyone, American or not, as long as you were not born in Cuba, are easy to obtain and come as a part of your travel package when you buy your ticket.   Visas for journalists and researchers declared as such are a separate matter and require an application to the Cuban Consulate in your  country (Washington, DC for the US).   Cuban Americans born in Cuba also need to  get special permission as they are viewed with somewhat more suspicion.

Be sure to understand some essentials of Cuban law.  You will need to have a hotel room arranged in Cuba before you get there, or at least have one to declare to Imigracion when you arrive. You can stay at a friend's house or a licensed private boarding house, but we suggest you do that only if they have  cleared the way for it. 

Cuban citizens can be fined $1,000 (a fortune in Cuba)  for having a foreigner as an overnight guest if they themselves don't 1) get permission from Imigracion or 2) pay $100/month or more for a license. This fine  can be doubled if not paid in 30 days, after which they go to jail at the rate  of $1/day.   Cubans can get permission to have a foreign friend stay at their  house, but this requires that they go and declare you with Imigracion and you  will need to go and show your passport. 

Note for Americans: in order to stay at a friend's house in Cuba, you may  officially need, in addition to your visa, a special A2 permit which can only be  obtained in advance from the Cuban Consulate in Washington,  DC, though it remains unclear if this is really true, or if it is, how widely the law is understood even by authorities in Cuba.  

This visa is de facto only available to those traveling with a valid Treasury license since anyone  contacting the Cuban Consulate will be logged in by the US.  Cuban officials  explain that this is because they are in a virtual state of war with the US and need to maintain their vigilance.  

If as an American, you do not obtain this permit and stay in a private Cuban house, you may be exposing that person to  fines.  

This law is not always strictly enforced, especially in Havana, but the  risk of penalties are there.  Update (3/99): more officials in Cuba seem to be  saying that, even as an American,  you can get permission to stay in a private  home down there, though that varies, as some will say that it only applies to blood relatives, except in the case of a licensed boarding house.

Once in Cuba, be aware that some Cubans are eager to hustle you and that this  can be severely punished - prostitution can get the woman 5 years in jail and, under the new laws, 20 years for the pimp.  

There is a crackdown under way and  all kinds of informal street vending are being punished by fines and jail time.   Ordinary Cubans walking the streets with foreigners are automatically subject to  a check on ID papers to the point where many Cubans refuse to walk with  foreigners as they could be fined if their papers are not in order.  For the current state of the streets, check out the Chismes sections.

In general, Cuban police lean over backwards not to molest tourists since  they are dependent on tourism for income.

Personal security on the island  is in general quite good.  Until recently, crime was little known.  That is changing with the continued economic hard times and we have seen a rise in crime which reached dangerous levels in certain areas such as Old Havana (Habana Vieja) and parts of Santiago, where purse snatchings and muggings have been  common.   

Because of this, there is now extra vigilance by the police who have  taken to asking  for IDs a lot more frequently and crime has gone down.  Such ID  checks are common in tourist and high visibility areas such as the Malecon along the Havana shore.  It is less common in non-tourist areas.  

There are recent changes in the penal code  which drastically increase prison sentences, though  prisoners are eligible for parole after serving half of their sentences unlike say in the US where parole is increasingly not part of the picture.  

Already a Cuban can get a jail sentence of up to 70 years for fighting with or attacking a  tourist. Even so, best to consult local Cubans on what are the safe areas and what aren't.  However, with the recent crackdown, folks report that foreigners feel they can walk the streets again...

The level of crime even in the worst places is probably not even comparable  to US levels, though hard numbers are hard to come by.  Many Cubans are in fact  supportive of the current crackdown as there is a tremendous personal fear  triggered by a few murders.   They have nothing to compare this to, and are  unaware that their murder rate is far, far less than what can be experienced in any major US city.

Money

Credit cards, including Visa/MasterCard, and travelers' checks are recognized  in Cuba so long as they are not from a US bank.  This is not Cuban law, but  American!    The US dollar is recognized everywhere and travellers need not change into pesos.

Travelers coming from the USA will typically have to pay hotel bill in $US cash, since no US based travelers’ checks or credit cards can be accepted.   However, if you travel through a third country, you can buy travelers' checks there before getting into Cuba, such as Thomas Cook checks, and they will be recognized in Cuba.

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