Everything You Need To Know Before Traveling To Cuba (Especially For Americans)

12 mins read


John and Sly similing at each other at the waterfront in Havana, Cuba
12 mins read

Cuba is truly unique. It is like nothing you have ever seen and nothing you are likely to see anywhere else in the world. This makes it a truly bucket-list worthy destination. Isolated by much of the world since the late 1950’s, the country seems frozen in time; the cars, buildings and infrastructure remain unchanged since the Cuban Revolution that ended in 1959.

Colonized by the Spanish in the 15th century, the island has heavy Spanish influences in language, dance, architecture, art and religion. The introduction of Caribbean and African slaves starting in the 17th century brought with it another dimension to its culture. You can see this mix in the music, dance, food and art. Today Cuba is a kaleidoscope of different cultures and colors that blend beautifully to form what is a uniquely Cuban melting pot. Couple this with amazing coast lines and fertile landscapes filled with all sorts of greenery, it is simply amazing.


Enjoying the amazing scenery on our way to the tobacco farms (Viñales). Selfie by John N. Njoroge.


The short answer is yes! But it is a little more complicated than simply buying your ticket and packing a bag. Recent years have seen a sharp increase in American tourists going to Cuba mostly due to the easing of sanctions by the US government during the Obama era. President Obama even become the first sitting president to visit Cuba since 1928. Unfortunately, this easing of sanctions did not last long once Obama left office. The new regime has made it more difficult to travel, but not impossible. According to the treasury department, for an American to travel to Cuba, they will need to fit in to one of these 12 categories

  •  Family visits;
  • Official business of the U.S. government, foreign governments, and certain intergovernmental organizations;
  • Journalistic activity;
  • Professional research and professional meetings;
  • Educational activities;
  • Religious activities;
  • Public performances, clinics, workshops, athletic and other competitions, and  exhibitions;
  • Support for the Cuban people; (This is the way to go, I will explain)
  • Humanitarian projects;
  • Activities of private foundations or research or educational institutes;
  • Exportation, importation, or transmission of information or informational materials;
  • Certain export transactions that may be considered for authorization under existing Department of Commerce regulations and guidelines with respect to Cuba or engaged in by U.S.-owned or -controlled foreign firms.

Anyone who travelled to Cuba pre-November 2017 is probably aware of a category not listed above known as “people to people” travel. That was an option that was available in the Obama days that allowed for Individual Americans to travel to Cuba. That option is no longer available. So, technically, it is illegal to travel to Cuba as an individual tourist. So how do you legally travel to Cuba? “Support for the Cuban people” in the above list is the way to go. Any other option may require you to obtain a license from OFAC (Office of Foreign Assets Control) and that can be a lengthy process. So here is how “support of the Cuban people” works: Only group tours arranged by an American based tour company are permitted. While in Cuba, you are required to;

“…engage in a full-time schedule of activities that enhance contact with the Cuban people, support civil society in Cuba, or promote the Cuban people’s independence from Cuban authorities and that result in meaningful interactions with individuals in Cuba.” – (treasury.gov).

If you meet this criteria, you qualify for a general license and do not need to apply for further authorization. Don’t worry, It isn’t as complicated as it sounds. You just need to have your entire trip planned through a US based tour operator and you are good to go. However, booking a trip through a US based tour company in order to meet the above requirements can add considerable cost to your budget, but there is a relatively inexpensive way to meet this requirement. By using a website called ViaHero.com you can meet this requirement for a fraction of the cost. The website qualifies as the US based tour company and plans out your “group” tour for you for as little as $25/day. You book your airline and accommodation, and they arrange your day to day activities. Viahero tour guides are aware of the new requirements and will tailor your itinerary to ensures that you have met the required “meaningful interactions” but also, and more importantly, they will help you avoid doing business with “the restricted list” which is a list of business that you should have no direct financial transactions with. We actually printed out the list (about 12 pages) and travelled with it. Not only for reference while we were there, but also to show the customs official upon our return that we were fully aware and compliant with the embargo. You will also need to have your itinerary with you when returning as you may be asked to show it at your entry port back into the US. The ViaHero website requires a minimum of 7 days for your tour guide to plan your trip so plan ahead. We booked our tickets rather last minute and only had 3 days to get our itinerary sorted. After frantically reaching out to ViaHero for help, they reiterated that seven days was needed for the process. Lucky we had reached out to individual tour guides on the site and one of them promptly wrote us back and said he could do it. Not only did Hugo (thats was our heros name) put together an amazing itinerary, but also did it in less than 24 hours. Hugo is based in the UK but has extensive knowledge of Cuba so you are not losing out by getting a non-cuban to put your trip together (all other Cuban experts on the site are based in Cuba). In fact there was an advantage to using Hugo, he was very responsive. Probably because of superior internet access where he is based out of unlike his Cuban counterparts that may not have such ready access. Keep in mind that wifi in Cuba is scarce (more on that later) so your Cuban based expert may take a day or two to reply so the more time you can give this process the better. Please note that ViaHero.com does not provide visa services.

A lot of Americans travel via an intermediate country like Mexico or Panama so as not to have to comply with the above requirements. This is a myth. The requirements for Americans traveling to Cuba even via  intermediate countries are the same as traveling directly according to the treasury website. Save yourself the hustle and money of having to connect via Mexico and just fulfill the requirements. As we were leaving Cuba we noticed the check in line to Aero Mexico, the Mexican carrier, to be at least 2 hours long by our estimation. Its not worth the hustle.


The Havana port is situated right in the city, ideal for a day of sightseeing. Pic by John N. Njoroge.

ALL SET TO GO? Here are some things you should know.

Buying your airline ticket:

Some popular flight search engines will not display flight options to Cuba but American carriers do fly directly to Cuba. Airlines including American, Delta, Southwest, JetBlue and United offer US to Cuba services. You can also purchase a cruise through; Carnival, Norwegian, Royal Caribbean and a few other companies departing from Miami.

You will need a Visa to enter Cuba if you are American and most other countries as well. The visa costs $50 each for Americans plus a processing fee that is charged by the vendor (depending on who is selling the ticket). For non-American travelers, click here  for visa requirements. All the airlines I mentioned above can assist you in getting a visa. The procedures and fees are ever changing so I will not list them here. But, when considering an airline, also consider what their Visa procedure and cost is. Alternatively, you can buy your visa online at cubavisaservices.com for a $35 processing fee and shipping or cubavisa.net for our European travelers.


You will need to carry your entire budget in cash (don’t worry, Cuba is pretty safe). ATM cards and credit cards do not work in Cuba. Remember the embargo? Well, trying to use your card or even accessing your account online while in Cuba is a sure way to get your account frozen by your bank. Banks are restricted from conducting business in Cuba. Avoid taking US dollars to Cuba because there is an up-charge when converting them. I would suggest exchanging your money in the US for Mexican pesos or Euros before you travel as this currencies are exchanged in Cuba without penalty.

There are two currencies in Cuba; the Cuban peso used by Locals (CUP) and the Convertible peso (CUC) for tourists. When you exchange your money at the airport, you will get CUCs and will trade in CUCs for your entire stay. Most, if not all items for sale are listed in CUC including menus at restaurants so you will not need to do any converting. The CUC is usually pegged to the US dollar or the Euro on a 1:1 exchange rate based on whichever is stronger. When we travelled it was pegged to the Euro which is currently exchanging at 1:1.24 to the dollar (which means $1 is about .80 euro) so for every dollar, we got .80 CUC and thus lost some purchasing power in the exchange. Factor this when doing your budget. The Cuban peso is worthless to you so be very cognizant of the change you receive as locals have been known to slip in some CUPs among the CUCs. Your notes will always say “peso convertibles” on them. Being short changed is also common, so always count your change. Quick side note on exchanging money at the airport; the lines can be very long. Once you go through Cuban passport control, split up and have one person wait for the luggage at baggage claim while the other lines up to exchange the money. Both this processes can take a long time so doing them concurrently will save you a lot of time


There are no Uber-like services in Cuba. Your options from least to most expensive are: local buses; we did not try this option but if you are on a shoestring budget, you will need to figure out the routes and times. If using a bus service for inter-province travel, arrive early to the bus station.Taxi collectivo; These are older classic cars that travel on a set route and are shared along the route. You simply flag one down along the route, hop on and state your exit point (in Spanish) and you are set for about a CUP. Older taxis: (Usually smaller Russian made cars called LADA) You can rent these out by negotiating a set amount for a set destination. Always bargain when negotiating a fare. Yellow taxis; These are metered and expensive.


Russian made LADAs, mostly used as taxis. Pic by John N. Njoroge

Havana is very walkable, so with good planning, you can minimize the use of taxis. Side note: Everywhere you go you will find people asking you if you need a taxi. Most of these people don’t actually drive a taxi but get a kick back from the taxi driver. Avoid unsolicited offers for a taxi. Actually, avoid any unsolicited offers period! (More on this later). When booking a place to stay, ask your host if they can arrange transport from and to the airport. It is very convenient to have this prearranged.


Use AirBnB to book a casa particular (apartment) or a room in a house. Do not book a hotel room because are they not only ridiculously expensive but also some are on the restricted list. Do your homework and research the ideal area to book for your trips needs. We rented an apartment in the Vedado neighborhood which is close to El Malecón (the ocean front walkway) and close to old and new Havana for $44/night. Our host even provided us with a phone to use while in Cuba which was very helpful. If you do stay at this apartment, do not buy anything at the liquor store that is across from the Cohiba Hotel (which is close by)! They sell liquor that has been diluted with god knows what and their water bottles are not sealed.


Locals hanging out along Avenida de Maceo (Malecón) on a Saturday night. Pic by: John N. Njoroge

Couch surfing is illegal, all occupants have to be registered. Your host will need your passport information to register you as occupants. This is a legal requirement.


Your ViaHero tour guide will have listed a bunch of restaurants that he/she would recommend based on the area of town you will be visiting on a particular day or your host will most likely have a list of restaurants they will recommend. Use these recommendations. It will help you avoid restricted list businesses and will also guide you to the best restaurants. If venturing out, try and stick to restaurants with a listed menu and pricing to avoid being ripped-off. Again, avoid unsolicited offers to direct you to a good restaurant. Tip the wait staff and bartenders. 5% percent is standard, +1-5% if you want to be generous.

I have heard people say that they did not like the food in Cuba, I guess this is a matter of taste. We thoroughly enjoyed the food. The fresh pressed juice served everywhere is heavenly. The food is all organic and tastes true even with minimal seasoning (seasoning is scarce). Chicken tastes like chicken, not bbq sauce or whatever marinade has been put on it. I have always found the meat in the US rather tasteless unless heavily seasoned, this is not the case here.

Do not drink the tap water. We did not even use it to brush our teeth! Carry anti-diarrhea pills, travel diarrhea is common.

Internet and Phone:

Do not expect to have unlimited access to internet while in Cuba. In fact, expect to have very little access if any. There are WiFi hot spots around the city, just look for ETECSA kiosks. Here you can buy a card that will give you a password to access the surrounding Wifi. It costs a CUC per hour and the signal is not strong.  The WiFi is only available within a 100 meters or so of the kiosk. Alternatively, you could go to a hotel and use their internet cafes for a fee. These usually have a considerable wait time.

Your phone carrier may offer voice and text service in Cuba (verizon does) but this is usually at a premium. You can buy a SIM card at the airport and switch it with your current SIM if your phone is “unlocked”. Thankfully, our host provided a phone for us while we were there so we didn’t need to do this. Check with your host before traveling for assistance.

With little to no access to technology, it is imperative that you be proactive. Print all documents before traveling. Print everything from boarding passes to reservation confirmations. Download offline maps to use while in Cuba. We downloaded the Havana map on the google maps app and it proved invaluable while navigating the Havana streets.

Other helpful apps to use are language translation apps that you can use offline like Itranslate.


Ask your ViaHero guide to help plan any tours you are interested in. Arranging tours ahead of time will save you a lot of headaches. We booked a vintage car day-tour to the Vinales (tobacco farms) for $130 and an extra $30 for an English speaking guide through cubawithyanara.com (with help from our ViaHero guide). I highly recommend you include the English speaking tour guide when booking these tours. Our guide’s name was David Padilla, request for him by name when booking your tour. You will be glad you did, he is superb. Word of caution; the restaurant that they stop at for lunch will over serve you on food and over-price the bill.


We ordered two food items, got 10 and paid the price.

That was disappointing after such a positive experience. Don’t expect the tours to be like what you would imagine a day tour in the States to be filled with flash and pomp. These are simple people with simple ways.

Hid this government warning when booking your tours.

david and sly

Our Handsome guide David helped us discover the Cuban countryside. Pic by John N. Njoroge


Here is the info for the US embassy in Havana. They do have a travel advisory at this time against traveling to Cuba and also point out that the embassy is being ran by a skeleton crew so help will be rendered only in emergencies.

You will be required to get health insurance while in Cuba which will cover any treatment you may need. Get extra travel insurance.

Avoiding scams:

Do not under any circumstances engage with anybody with whom you did not initiate the conversation. This sounds anti-social but trust me, it is going to save you a lot of money. While in Cuba you will be approached numerous times by people asking if you have eaten or if you need a ride etc. Most of the time they will ask you out right if you need A or B but sometimes the conversation will start off as friendly banter, like asking “where you are from?” and so on but, it always ends up in the same place. They will want to take you to a “locals” spot to experience true Cuba or the cousin is in the Cigar business and will get you the lowest prices on Cigars or there is local cooperative where locals get their cigars for cheap and he can get you in…the list is endless. If you agree to any of these, you are going to be ripped off! Guaranteed! The cigars will most likely be fake and the restaurants over-priced.

As I mentioned earlier, short-changing is pandemic in Cuba. Most of the time it is .50 cuc or so and they know most people won’t fuss about that.

Its sad really how much scamming goes on in Cuba. I understand that poverty necessitates some of these unfortunate actions, but I believe they are scaring off would be and repeat visitors. Can you imagine getting back home only to realize that your prized cigars, the very thing that took you to Cuba, are fake. It is a rather shortsighted approach from people that rely so heavily on tourism. I have Stories for days regarding this but I will leave it at; Do not under any circumstances engage with anybody with whom you did not initiate the conversation.

Customs and the government:

You can bring back up to $100 worth of cigars and rum, up to $400 worth of souvenirs and an unlimited amount of art purchased from locals or unrestricted vendors. Stay within these limits to avoid problems when reentering the country. Also, always ask for receipts for all your transactions while in Cuba. Some places my not have the capability to provide one, but ask anyway and keep track as much as possible. The treasury department requires you to hold on to all your receipts for 5 years after travel for auditing purposes. You do not want to be audited and don’t have those receipts, although audits are rare. As stated earlier, keep the itinerary that you got from your American tour operator with you as they may want to see it when reentering.


All information provided here is not intended to be legal counsel. Always seek professional advise for your travels, we are not professionals. This is merely a product of our meandering research prior to our trip. This information is for entertainment only and subject to change. The publishers will be held harmless by providing this information. Happy travels!

11 Thoughts to "Everything You Need To Know Before Traveling To Cuba (Especially For Americans)"


  1. Maricela on March 3, 2018 at 8:15 pm

    OMG!!! Sylvia THANK YOU!!!
    Thank you for all the research and information. You are absolutely a resource of knowledge. I will follow your advice when I take my son to Cuba. Your husband is so lucky to have you by his side. I think you guys make a beautiful couple.

    • twosidedcoin on March 8, 2018 at 9:24 pm

      Thankyou Maricela for taking the time t read my blog. I am sure you and your son will enjoy Cuba together!♥️

  2. Claudia Obando on March 4, 2018 at 8:39 am

    I enjoyed reading about your traveling adventure to Cuba. Thank you so much for all the info and tips. I can’t wait for your next story.

    • twosidedcoin on March 4, 2018 at 11:10 am

      Thank you Claudia for taking the time to read about my adventures. It means a lot to me. Share the blog with your friends and family that want to travel to Cuba✊🏽

  3. Alex on March 4, 2018 at 10:09 am

    Awesome, nice article good research. What are the places you must visit in Cuba?

  4. Marilen on March 4, 2018 at 12:08 pm

    Wow! Very informative. Thank you!

    • twosidedcoin on March 4, 2018 at 3:47 pm

      Thank you for your continuing support Marilen👍🏽♥️

    • twosidedcoin on March 7, 2018 at 6:14 am

      Thanks for your support and glad you found this piece helpful.

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