Check departure times of flights from Cancun or Mexico City to Cuba. The two principal airlines that fly this route are Mexicana and Cubana. Both have regular scheduled flights that you can check the times of online. (see Resources)
Book a plane ticket to either Cancun or Mexico City. Arrange to arrive two hours before a scheduled flight to Cuba.
Book a connecting flight from Cancun or Mexico City to Cuba.
There are three ways to do this.
Purchase your ticket at the airport in either Cancun or Mexico City, using cash. This is the easiest and most reliable method.
Book using a travel agency not based in the U.S. According to Andrew Cohen of Travel and Leisure, almost any travel agent outside the U.S. will sell you a ticket to Cuba. Cuba Linda is one such travel agent you can access online. (see Resources)
Book directly with either Mexicana or Cubana airlines. You can do this online.(see Resources)
Purchase a Cuban Tourist Visa Card. You will need one of these to enter Cuba. They are good for 30 days and available from the airport desk in Cancun or Mexico City.
Purchase health insurance upon arrival in Cuba. This can be done at the airport and is necessary for entry into Cuba. You can, of course, purchase your health insurance before you fly, but it cannot be from a U.S. insurance company.