Cuba was filled with colors, culture and amazing hospitality! I received a lot of questions regarding what we did and how we traveled there from the States soooo here are all your questions answered!

Traveling to Cuba from the US

Contrary to what people want to make you believe (aka our current President) it is not difficult to travel to Cuba from the U.S. Let me walk you through the steps you need to take to prep for your next visit!

Is it easy to get a plane ticket? Where can I fly from?

Yes! It is easy to get a plane ticket and you can virtually fly from anywhere in the states. Now there are very few direct flights from the US to Cuba, here are the cities that provide them:

  • Houston

  • Newark

  • Fort Lauderdale

  • Tampa

  • Orlando

  • New York (JFK)

  • Miami

  • Atlanta

  • Charlotte

  • Los Angeles

If you are traveling from any other city you will need to take a connecting flight which isn’t out of the ordinary. If you do live in one of these cities a connecting flight (other than from Florida) might be a cheaper option for you!

Visa!? Visa!? Visa!?

Visas….one of the top questions asked! So you do need to purchase a visa to travel to Cuba and you are only allowed to pick from these 12 categories:

  1. Visiting family

  2. Humanitarian projects or to provide support to the Cuban people

  3. Official business of the U.S. government, foreign governments and certain intergovernmental organizations

  4. Journalistic activities

  5. Professional research

  6. Educational activities by persons at academic institutions

  7. People to people travel

  8. Religious activities

  9. Public performance, clinics, workshops, athletic or other competitions and exhibitions

  10. Authorization to provide travel services, carrier services and remittance forwarding services

  11. Activities of private foundations, research or educational institutes

  12. Exportation of certain Internet-based services

Since “technically” you can’t travel to Cuba for a vacation anymore under Trump’s new laws, you must be a bit more creative. For vacationers such as ourselves the best visa category to choose is Support for the Cuban people. The explanation is simple for this visa. As a US citizen you cannot spend money at government owned establishments so it’s easy to follow this category to the tee.

After you purchase your plane ticket you will receive an email from your airline that contains a link to purchase your visa. Depending on the airline the visa prices range from $50 - $100. Some airlines will allow you to order online and have it shipped to your house (Southwest has this option) and some will only have the option to buy it at the airport (JetBlue has this option). Buying it at your connection city before your Havana flight won’t be difficult or cost more than ordering it online.

Getting Through Customs. What do I need?

 After you have your plane ticket & visa there is only one more step….AN ITINERARY! This is a cautionary step but necessary, all the blogs I read stated you needed an itinerary for your plans in Cuba. Traveling to Cuba and going through their customs is pretty simple; all you need is your visa & passport. Coming back to the States there have been incidents where customs will ask for proof on how/where you spent your money, to make sure none went to government owned establishments.

All my friends that traveled to Cuba under the new law had no issues coming back through customs and neither did we. We weren’t asked for our itineraries, but I had it printed and ready because you never know if you are the random person that gets asked.

For me creating the itinerary wasn’t anything out of the ordinary, since I create one for every trip. Lucky for you, all the information you need for your itinerary will be below!

Planning Your Trip 

Airbnb vs. Hotel. Which should I choose?

Airbnb! If you are traveling from the States, Airbnb’s are Casa Particulars (independently owned homes) so it’s a perfect fit! Hotels are government owned and don’t give you the authentic Cuban experience.

With an Airbnb you will be staying at someone’s home, like any other Airbnb butttt it’s a completely different experience. At our Casa we had breakfast cooked for us every morning in our kitchen and was checked on by the family to make sure we had everything we needed. Casa’s are also usually located right in the middle of everything! From the center of the different Plazas in Old Town Havana to the center of all the popular areas in Havana.

Since Airbnbs are very popular you need to book at least 2 months out if not sooner or the best places will be gone. For our May trip I booked the Airbnb in February and at that time our Airbnb was already booked in April.

Our Airbnb: Yohan & Familia 1 (Plaza Vieja)


Where Should I Stay?

Best places to stay in Havana include any of the major Plazas:

  • Plaza Vieja - The Old Square

  • Plaza de la Catedral

  • Plaza de San Francisco

  • Plaza de Armas

What are some other cities in Cuba I should visit other than Havana?


  • Famous for its tobacco farms and beautiful sights of never-ending greenery. Perfect place for hiking, horseback riding, learning about indigenous coffee, fruits and tobacco. It’s about 3 hours away from Havana and a great option for a day trip!

*Shot on Sony a6400

*Shot on Sony a6400



  • This is Cuba’s most famous and beautiful beach! Filled with turquoise colored water and powdery sand, many people make the trip from Havana during their visit. It’s about 2 hours away so a day trip is very doable.

*Rights: Weather2Travel.com

*Rights: Weather2Travel.com



  • Trinidad is in the center of Cuba and about 4 hours away from Havana. This city is known for its colonial town center, many museums and historic buildings. Playa Ancon is the closest beach to Trinidad and is considered one of Cuba’s top beaches.

*Rights: Best Cuba Guide

*Rights: Best Cuba Guide


*Keep in mind how long you are traveling to Cuba for and how much time you have for day trips. Touring Havana itself gets exhausting, so within a 5 day trip you might only be able to do one of the cities above. *

Gelila Kebede