My $27 Flight to Havana



Permitted travel to Cuba

Strictly going to Cuba for tourism is still forbidden without a special permission from the US government. There are currently 12 reasons that will not require this special permission.

  1. Family visits
  2. Official business of the U.S. government, foreign governments, and certain intergovernmental organizations
  3. Journalistic activity—-Hola
  4. Professional research and professional meetings
  5. Educational activities
  6. Religious activities
  7. Public performances, clinics, workshops, athletic and other competitions, and exhibitions
  8. Support for the Cuban people
  9. Humanitarian projects
  10. Activities of private foundations or research or educational institutes
  11. Exportation, importation, or transmission of information or information materials
  12. Certain export transactions that may be considered for authorization under existing regulations and guidelines.

If you do not qualify for one of these and are caught traveling to Cuba, you can face fines or even prison.




I recently received Mosaic status from JetBlue which gives a few perks like boarding first, free alcohol on the flight, having your checked bag put on the plane last so that it arrives first, and 15,000 bonus miles upon achieving Mosaic. I reached this level by signing up for both the personal and business credit cards that they offer. These also get you 50% off food purchases in-flight among other benefits. The flight that I booked ended up costing 12,100 points plus 2,000 for Even More Space seats on all of my routes for a total of 14,100 plus $77.66 for taxes and fees. I received a points rebate of 2,602, and since my flight from Fort Lauderdale to Havana was delayed, a $50 travel credit. This made my total cost 11,498 points and $27.66.


No Mobile Check-In

When leaving Pittsburgh, I was not able to check in with my phone or with a kiosk, so make sure that you leave yourself enough time to wait in line to see a gate agent.


When you are leaving Havana, three hours ahead of time may not be enough!! There were two flights leaving within 20 minutes of each other and the line was out the door. Make sure you arrive at the airport with plenty of time to spare!


Health Insurance, Travel Visa, Immigration Forms

Cuba requires you to have health insurance while you are in the country. The price of this was covered with my ticket from JetBlue.


You will need to purchase a travel visa before you arrive in Cuba. There was a kiosk near the gate in Fort Lauderdale that will assist you with this. The cost was $50 which is cheaper than other airlines. You can get them for a little cheaper online if you plan ahead.


You are required to fill out both a declarations form and an illness form. When you arrive, you will first go through an immigration station, go through a metal detector, retrieve your bags, and then head to customs. I would highly recommend not checking a bag; it took about an hour for it to arrive. Customs was a breeze since I had nothing to declare. I walked down a hall, handed the agent my form, and was through.


Exchanging Currency

You will need to exchange USD for CUC to use taxis, eat, buy things, etc. There is a 10% tax on USD plus an exchange fee. You will receive about 87 CUC for 100 USD. If you are able to take Euros, Canadian Dollars, or British Pounds, you will be able to avoid the 10% tax.


There are two places to exchange currency in the airport. The station on the ground floor was a two-hour wait. The station on the second floor of the airport was a 5-minute wait. GO UPSTAIRS!



I was able to get a taxi right away, but I am pretty sure that I was slightly fleeced. The cost was about 40 CUC, but this should have been closer to 30 which is what my return taxi cost. Some taxis will have a sticker in the window that states the flat fees for airport transportation.



I was able to book an Airbnb for $35 a night. The house was great, the people were very friendly, and the rate is hard to beat. I was staying the heart of Chinatown so I got to see how the Cuban people really live day to day. This was a great experience in my opinion. I felt safe while I was walking throughout the day. Since I was alone, I did not stray too far at night, but never felt like I was in any real danger except for a few middle schoolers who I am pretty sure were making fun of me. I was approached with offers of taxis, cigars, souvenirs constantly, but a simple smile and no thank you was enough for them to move on.


You may need to bring an outlet adapter since their outlets have different voltages which may fry your batteries if it is too powerful. I was able to get by only charging my phone once since I was not using it throughout the day.


Only drink bottled water, and remember this while you are brushing your teeth.



The only place that I was able to get Wi-Fi was in the larger hotels. I avoided conducting any business or sending any sensitive information while I was there since the government supposedly monitors the internet. Even if your Airbnb host says that they have Wi-Fi, it is not going to be what you are used to. I also arrived at a hotel 7 am and was told that the internet in the country was not on yet.


Since you will not be able to use Google Maps, I would advise printing out points of interest and bringing a paper map. At the time, I was not able to download the area in the Google Maps app on my phone for offline use either.



You will need to know some to a lot of Spanish depending on the area that you are in. I was able to get by with recalling what I had learned in college, but would definitely practice a lot more if I were to go back. Playing charades may also be of some benefit.



Almost every person that I ran into was interested in selling me Cuban cigars since they had an inside connection. These are almost guaranteed to be fake and there are multiple articles online that will help you distinguish between real and fake cigars. La Casa del Habano is a government approved store in the Miramar district of Havana. If you are really interested in getting cigars I would suggest heading there. You will also get to see the part of the city that the foreign dignitaries chose to live.



As I said previously, make sure that you give yourself plenty of time to check in at the airport. Once you make it through the line and receive your boarding pass, you will have to go through customs and security as well. Customs and security did not take as long as I thought they would, but I would error on the side of caution.


Once you are through, there is a duty-free shop that accepts USD. There are no Cuba-specific dollar limits anymore, but you will have to pay duty if you bring back more than what is allowed by US law. If you have a connecting flight in the US, you will need to go through security again once stateside. For you to be able to bring liquids through security, you will need a receipt in every duty-free bag and the date has to be on the receipt. I had to go back and check a bag since I did not meet both of these requirements.



Although I was only on the ground for about 45 hours, I am glad that I made the trip. It was definitely an eye-opening experience to see real Cuban life. If my journalistic activity services are required, I would be happy to make another trip.


Thanks for your time,









Bulldog Advisors LLC is a registered investment advisor.  Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies.  Investments involve risk and unless otherwise stated, are not guaranteed.  Be sure to first consult with a qualified financial advisor and/or tax professional before implementing any strategy discussed herein. Past performance is not indicative of future performance.

Leave a Reply

Your email address will not be published. Required fields are marked *