Transport of marijuana in states where it is legal to islands located within the state is complicated by the fact that transportation by air generally violates federal law. Rule 91.19 of the Federal Aviation Regulations (14 CFR 91.19) generally prohibits civil aircraft from knowingly transporting marijuana and other types of illicit drugs within the US. The prohibition initially applied to flights between US and Mexico but was subsequently amended to include flights solely within the US. However, the rule contains an exception for the transport of drugs "authorized by or under any Federal or State statute or by any Federal or State agency" and, as was recently reported by The Boston Globe (State Eyes Flight Rule to Ship Marijuana to Islands), the chairman of Massachusetts' Cannabis Control Commission is looking at the exception as a means to potentially permit air transport of marijuana to Martha's Vineyard and Nantucket.
A former Federal Aviation Administration ("FAA") lawyer quoted in the Globe piece raises the question of whether the exemption applies if use of the drug is authorized by the state or whether the transport of the drug must be expressly authorized by the state. The wording of the regulation does appear ambiguous in this respect and the FAA has not provided any guidance on the topic.
There are also published accounts (Weed On A Plane: How Alaska Businesses Get Pounds Of Pot On Board, With Police Blessing) of marijuana businesses in Alaska making use of the provisions of the regulation that the carrier only violates the rule if it knowingly transports the drug. The businesses inform the airport police and TSA that they are transporting marijuana and provide documentation of their authorization to do so. Neither the business nor the police informs the airline so it is unaware that it is transporting marijuana. In the end, with cooperative police, the more viable alternative may prove to be "don't ask don't tell" provided that the marijuana is packaged so as to disguise the smell.
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