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Legally Speaking: Update on Cuba Travel

Most of the time my legal training is not exactly relevant to the work I do in travel, but occasionally the realms of law and travel collide. Recently, this collision has happened in the balmy Caribbean breezes over Cuba.

When the Obama administration relaxed Cuban travel restrictions just over a year ago, I went straight to the source – the official Treasury Department regulations – to understand the rules. And I’ll be doing that again when the Treasury Department (which oversees all things Cuba-sanctions-related) issues new regulations in the coming months.

If you had hoped and dreamed of traveling to Cuba, hadn’t gotten around to it yet, and are now worried that you missed your chance – fret not. You can still go to Cuba.

Americans could actually go to Cuba prior to Obama’s diplomatic opening, and we’ll still be able to go after the new restrictions are in place, albeit with some extra hoops to jump through. So if Cuba is on your mind, here’s what you need to know:

  • If you’ve already booked a trip to Cuba, you’ll be “grandfathered in” and able to travel as planned.

  • Until new regulations are issued (which could take a few months), the current rules remain in effect. These rules allow you to travel on your own to Cuba, but it’s not unfettered. You must follow a full schedule of educational, “people-to-people” activities that bring you into contact with local people and introduce you to the culture. You should keep a daily journal of your activities and you need to hold onto your records for 5 years. It’s likely that even before the new rules go into effect, the Treasury Department will be auditing more travelers regarding their visits to Cuba – so don’t let these things slide.

  • After the new regulations are issued, you won’t be able to travel on your own to Cuba, but you will be able to visit as part of a group tour with a licensed tour operator. These are the types of trips that were available to Americans pre-Obama. As a big fan of group tours in general (obviously), I encourage you not to be turned off by this. There are many excellent tour companies that offer tours of Cuba, which will allow you to discover and explore the country without hassle and a minimum of hoop-jumping.

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