Of all the queries I receive about Cuba, one of the most frequently asked questions is: "How can I motorcycle through Cuba?" Well, there's good news and bad news. First the bad news. It's none too easy. There are no motorbike rental agencies (although you can rent poorly maintained Yamaha and Suzuki scooters from agencies in most major beach resorts). Nor are motorcycles available for sale. Unless you bring your own motorcycle (I'll get to that in a second), your only option is to negotiate with a Cuban for use of his untrustworthy Ural or MZ or even a venerable pre-revolutionary Harley!
As to shipping your own two wheels to Cuba, good luck!
In addition to the travel restrictions that apply to U.S. citizens and residents, no aircraft or seagoing vessel may visit Cuba without a relevant license from Uncle Sam. That includes private vessels too following onerous new restrictions imposed by the Bush administration. Sure, in 1996 I shipped my BMW GS100 to Cuba board a private vessel. But that was then. Things have changed. Uncle Sam has tightened the rules since I made my own motorcycle journey to research the first edition of Moon Cuba .
True, you may be able to secure passage to Cuba aboard a commercial aircraft (typical prices are $3 per pound, crated) or cargo ship departing Canada or Mexico or elsewhere beyond U.S. shores. And Europeans can do the same on vessels originating in Hamburg and elsewhere in Europe. But anyone under U.S. law should be aware that a motorcycle manufactured, registered, or otherwise originating in the U.S. is considered an "export" with regard to passage to Cuba, requiring a separate export license from the Commerce Department . Hopefully things will soon ease up under Obama, but current law means that you could pay an unbearable price for "trading with the enemy" if caught shipping "exportable items" in addition to merely transaction travel arrangements.
If you do get your bike to Cuba, things have also tightened up there, as Cuban authorities now require an international carnet or import tax equal to the value of the vehicle. Paying the tax in cash is asking for trouble when it comes to "payback" time (no other country in the world is so adept at not giving refunds). Corruption is rife. One friend (a U.S. citizen who shall remain nameless) who recently shipped his motorcycle to Cuba from The Bahamas had his machine confiscated by corrupt Cuban Customs officials.
Fortunately you can read all about my 7,009-mile sojourn in my award-winning literary travelog, Mi Moto Fidel: Motorcycling Through Castro's Cuba .
Oh, and to my knowledge the only foreign tour company currently operating motorcycle tours to Cuba is the Danish company, Moto Mundo .