Trips Travel Agency

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Departures: Getting to Cuba

In our new series Departures, were talking about exciting destinations and how to get there. First up in the series is Cuba!!

For over a year I've been fielding calls and questions on trips to Cuba.

If you haven't heard but getting to Cuba is the newest trend in travel for U. S travelers. Everyone wants to get there before things "change", "before it becomes overrun with tourists" or too "touristy" . All this makes getting to Cuba big business.

There are eager travelers ready to explore a destination that was relatively off limits for them in the past. While getting to Cuba is certainly now more accessible to Americans these days, getting there is not without its challenges. 

First comes the rules for traveling there. 

Once you attempt to purchase a ticket on JetBlue  (using them as an example because they happen to be my favorite airline) they will ask you to select the category under which you are allowed to travel to Cuba.  

1) I am a Cuban National and resident of Cuba
2) Educational activities, including people-to-people exchanges open to everyone
3) Professional research and professional meetings
4) Public performances, clinics, workshops, athletic and other competitions and exhibitions
5) Religious activities
6) Humanitarian projects
7) Journalistic activities
8) Family visits
9) Activities in Cuba by private foundations, or research or educational institutes
10) Support for the Cuban people
11) Exportation, importation, or transmission of information technologies or materials
12) Certain authorized export transactions including agricultural and medical products, and tools, equipment and construction supplies for private use
13) Official business of the US government, foreign governments and certain intergovernmental organizations
14) Specific license

(For more information:

If you dig a little further and go to the U.S. Treasury's page you'll find the following question:

Is travel to Cuba for tourist activities permitted?
No. Consistent with the Trade Sanctions Reform and Export Enhancement Act of 2000 (TSRA), travel-related transactions involving Cuba are only permitted for the 12 categories of activities identified in the CACR. Travel-related transactions for other purposes remain prohibited. 

( For more information:

Hey if you want to get to Cuba it's best to follow the rules.

This may all seem daunting but it's not! There are many ways to experience Cuba and meet the requirements of the U.S. Treasury. Currently the best way to do this is to go on a certified tour. Certified tours have already been through the vetting process of having their programs qualify usually under the people to people exemption. 

This means that your trip to Cuba will usually have an educational or cultural exchange aspect to it. 

Some tour options include jumping on a Fathom cruise.

Fathom is Carnival's newest cruise line sailing from Miami to either Cuba or Dominican Republic. These cruises allow you to take part in service projects, connect with the locals on a deeper level than you might on a regular 7 day cruise to the Caribbean. 

Additionally the cruise moves along to various ports within the country so you're not docked in one area for the entire trip. Your group tours are also small and intimate as opposed to the big bus tours that you would normally take on a cruise. Overall it's an intimate experience, even the ship they use, the  Adonia is a smaller ship making it much more of an intimate experience than your mega ships.  I wouldn't be surprised if you left making some lasting connections with the people on and off the ship.  

Another great way to experience Cuba is through Smithsonian Journeys. Smithsonian Journeys has in-depth tours on many countries. Additionally your hosts are usually experts on that particular country. You can also see their biography online so you can see their background before booking the trip. 

G Adventures is another great tour operator! They usually focus on small intimate groups and is best for the adventurous traveler. Try their Cycle Cuba or their Classic Cuba tour.

Things to Remember:

  • In the past many of the tour operators took care of processing the U.S. Treasury documents for you. Today some still do and some do not so it's always a good idea to ask. 
  • Cash is king here! You're US debit or credit card is not going to work in Cuba, so bring cash instead 
  • Don't forget to get the health insurance. Again some operators will do it for you or it's added onto their pricing others do not so check on it. If you purchase your flight separately ask if they also include it. 
  • Read the fine print! Operators will tell you whether or not this tour is suitable for US citizens.
  • Keep good records of your Cuba related  transactions for 5 years

Who Should Go:

This isn't your typical beach vacation with friends and family.  This is truly an educational experience. Do not expect all inclusive packages with unlimited beverages and all you can eat buffets or just buying a  $99 flight and winging it when you get there.  Costs and tours can vary so take a look around and see what fits your schedule and budget. 

Happy Travels!


    Additional Resources:

    US Embassy in Havana: