Go to U.S. Department of the Treasury website (see Resources) and click "Services." A page with a list of services provided by the Treasury Department subsequently appears. Select "Cuban Travel Licenses." A page showing an application for a travel license subsequently appears. This will allow you to legally travel to Cuba and spend money while you're there.
Scroll down and click the link entitled "Request a Specific License for Travel under the Comprehensive Guidelines for License Applications." Fill-out the displayed Web page to apply for your travel license. After completing the application process, wait for confirmation from the Treasury Department that your travel license application has been approved. After approval, you may now proceed to plan your trip to Cuba.
Book a flight to a foreign nation that allows travel to Cuba. Though you have a travel license, the United States doesn't allow American-based flights to enter the nation of Cuba. The best way to see if the nation you wish to go to allows travel to Cuba is to determine whether its national airline provides flights to Cuba. For example, if you want to travel via France, check AirFrance's list of available flights. Many countries allow travel to Cuba, including Canada, Mexico, the United Kingdom, and South American and Central America countries.
Book a flight from the foreign nation to Cuba. Make sure to separate your arrival and departure times by at least two hours for baggage to be transferred between flights.