The Ultimate Guide to Travelling to Cuba for the Habanos Festival

Planning your journey to the renowned Habanos Festival in Cuba requires a bit of preparation, particularly when it comes to navigating travel logistics. Whether you're flying from the United States or another country, understanding the rules, paperwork, and restrictions will make your trip smoother and more enjoyable. Here’s everything you need to know to make sure your travels are hassle-free.

For American citizens, traveling to Cuba is more straightforward than many people realize. While travel to Cuba from the U.S. is subject to the ongoing embargo, there are easily-accessible legal pathways available under specific categories, of which one one is “Support for the Cuban People.” This means that American travelers can visit Cuba without any formal Government visa or travel permission, provided they self-declare their purpose when booking flights and upon arrival at the airport. The required Cuba Travel Visas are purchased electronically (more details below). 

Both United Airlines and American Airlines offer daily flights to Havana from several U.S. cities, including Miami, New York, and Houston. The process of booking a flight to Cuba is just like booking any other international trip, but remember that you will need to declare your travel under the “Support for the Cuban People” category when purchasing your ticket. No formal “proof” is required and neither the Airline at check-in or U.S. Customs will ask for any documentation related to the category you select.

Due to the U.S. embargo, American travelers face some restrictions on where they can stay. Technically, U.S. citizens are prohibited from booking at any hotel in which the government of Cuba has an ownership interest (which is basically all hotels). However, larger hotels often have subsidiaries in Europe, allowing U.S. travelers to make reservations online. However, booking private accommodations listed on platforms like Airbnb is permitted under the “Support for the Cuban People” exemption. If you need help booking accommodations, please reach out to our Cigar-Keep Cuban Concierge via email at [email protected]. Alex is available to help coordinate every aspect of your next trip to Cuba. 

American travelers should also note that they are limited to one checked luggage piece for economy tickets and two pieces for business class. These restrictions apply to travelers flying with U.S. carriers, and it’s important to keep in mind when packing.

Americans now have the option to apply for their Cuban travel visa electronically, which makes the process much easier. (Previously, Travel Visas were purchased at the gate prior to departure to Havana). We recommend doing this no later than 48 hours before your flight to ensure everything is processed in time. Once your electronic Cuba Travel Visa is confirmed, you will receive an “Electronic Visa Number” that you will then need to to complete the online Cuban Travel Declaration Form, which will be required by the airline to check into your flight. 

To apply for the Cuba Travel Visa, visit Cuba Travel Services. Once you’ve received your visa number, complete the Cuban “Advanced Travel Declaration” online at https://www.dviajeros.mitrans.gob.cu/inicio (note that language can be changed in the top-right corner of the website). This form is free (do not fall for any scams that charge to complete the form for you) and must be completed prior to check-in. You can either print or save a screenshot of the QR code on your phone to show both your airline agent and Cuban customs upon arrival. 

U.S. Citizens travelling to Cuba cannot check-in online and should allow for extra time at the airport. When checking in, the airline agent will ask to see your completed Cuban “Advanced Travel Declaration,” will ask for the reason you are traveling to Cuba (“support for the Cuban people”), and for the address of where you are staying. As long as you have these pieces of information handy, checking should be easy and painless. 

U.S. Citizen Travel Checklist: 

• Apply for your electronic Cuba Travel Visa
• Complete your Cuban “Advanced Travel Declaration”. 
• Print the address of your hotel in Cuba to show to your airline check-in agent.

For travelers from countries other than the U.S., the process of traveling to Cuba is much simpler. Cuba typically does not require travel visas in advance for most countries, although some countries may have specific travel restrictions. To determine specific travel requirements, we recommend visiting https://apply.joinsherpa.com/travel-restrictions. Sherpa catalogs travel requirements specific to your country of citizenship and travel destination. 

However, there are important things to consider for travelers who may be transiting through the United States or who frequently travel under the U.S. ESTA visa waiver program.

If you are not a U.S. Citizen or do not hold a permanent U.S. Visa and are planning to transit the United States on your way to Cuba, it's crucial to understand that the U.S. government’s designation of Cuba as a “State Sponsor of Terrorism” (I know, absurd) carries serious implications for travelers. First, transiting the United States on your way to Cuba is strictly prohibited, even if you are simply “connecting” through a U.S. Airport. Second, travel to Cuba will invalidate your ESTA (Electronic System for Travel Authorization) visa waiver will be automatically canceled. This means that unless you have a valid U.S. visa, you cannot transit through the United States on your way to Cuba.

Even if an airline allows you to book a flight with a U.S. layover, your ticket may be canceled, sometimes even as late as 24 hours before your departure. Be sure to book your flight with no U.S. connections to avoid this issue.

Additionally, if you travel to Cuba, you will be permanently disqualified from using the ESTA program for future U.S. travel. You will need to apply for a full visa through the U.S. embassy, a process that can take several months, so it’s important to plan ahead if you anticipate traveling to the U.S. in the future.

However, if you have a valid U.S. visa (non-ESTA), you may transit through the U.S. on your way to Cuba. Always check with your airline for confirmation, as even they might not be fully familiar with these restrictions.

Once you’ve secured your flight and accommodation, there are a few more things to keep in mind as you prepare for your trip.

Luggage and Prohibited Items

Cuban security services are highly thorough when it comes to screening luggage. All bags entering or leaving Cuba are scrutinized carefully, and prohibited items are confiscated. To avoid complications, make sure not to pack anything that might be restricted or prohibited. Common items that fall under this category include illegal drugs, drones, and wireless microphones.

It's always best to pack light and smart, focusing on the essentials.

Health and Safety Requirements

Before entering Cuba, you will need to complete a Cuban health declaration form, which is a requirement due to the ongoing global health situation. This form can be filled out online at https://www.dviajeros.mitrans.gob.cu/inicio. Once completed, you will receive a QR code, which you will need to present upon arrival in Cuba.

By understanding the travel logistics, visa requirements, and restrictions, your journey to the Habanos Festival will be far less stressful. With a little preparation, you can avoid any surprises and focus on enjoying the incredible experience that the Habanos Festival has to offer.

Stay tuned for the next part of our guide, where we’ll dive into the best places to stay, eat, and shop while attending the festival.

Links to Useful Resources:

• Cuba Travel Services
• Cuban Advanced Travel Declaration
• Travel Sherpa