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What is your home city/country? How long is the trip to post from there, with what connections?

D.C., no direct flights, connect through Miami, Charlotte, or Atlanta. - Oct 2, 2017
Western U.S. Due to the charter company layover in Miami, this trip takes longer than it appears on a map. We generally have to sleep in Miami in at least one direction, usually in both directions. This may improve with the anticipated commercial flights, as these should allow you to check your bags at a normal counter on one end of your trip, and retrieve them on the other end, without having to essentially leave the airport and check back in again in Miami. - Jan 2, 2016
Washington, D.C. Theoretically, only a few hours. However, it can take as long as two days to reach any U.S. destination other than Florida because charter flights between Havana and Florida cities (first leg) are infrequent and unpredictable. For example, you may arrive at the aiport in Havana to learn that your 11am flight has been changed to 5 or 8 pm. Since the charter companies are not affiliated with the major airlines in the U.S., some travelers have missed their connecting flights and simply had to buy new tickets. Because the risk is high that you will miss your connecting flight, many simply schedule an overnight in Miami/Tampa and connect the following day. - May 4, 2014
Chicago. About an hour flight to Miami if all goes well. If all goes off the rails you can be stuck in the airport for 6 or more hours. This has happened on numerous occasions between 2012/13 and has affected everyone and including the Chief of Mission. Many people stay overnight in Miami rather than chance missing their connecting flight. Airlines will generally not rebook you for missing a connecting flight as they are not in the same system as the U.S. Treasury Charter Flights. The Tampa flight is more reliable but does not fly as often. - Aug 14, 2013
It's a one-hour flight from Miami. - Jul 9, 2011