We Are Travel Girls may collect a share of sales or other compensation from the links on this page.
“Havana oh na na na.” Definitely a place to leave your heart, and it will take everything to not caption your Instagram photos with this song. A country that has remained elusive, mysterious, and exotic to Americans for decades, Cuba has become accessible in the past few years.
Despite the opening of its doors, Cuba still isn’t the kind of place you just hop on a plane and go to, even though a flight from NYC is literally three hours. Traveling to Cuba as an American can definitely feel like a process due to the ever-changing rules and sanctions. Having now gone through the experience, I can drop some knowledge on what to plan in advance and what to expect when going through customs when visiting Cuba!
BRIEF HISTORY OF U.S. CUBA RELATIONS
In 2014, Obama began to normalize relations between the U.S and Cuba and created a list of categories that would make traveling to Cuba legal for Americans. One of these categories, People to People interaction, became the easiest and best way for Americans to qualify for a visit. It enabled Americans to travel freely in Cuba without a set itinerary or tour group. Unfortunately, in 2016, when Trump became president, things got a bit trickier.
Trump placed stricter restrictions on Cuba travel by eliminating the People to People category. This left me (and probably a lot of other Americans) kicking myself for not going sooner. The changes did, however, make me jump into action in fear of travel to Cuba for under any reason becoming closed off again.
After doing some research, I learned the next best way to legally travel to Cuba is under the Support of the Cuban People category. My first question with this was “wait, does this mean I have to go with a tour group?” As someone who prefers to travel independently, this made me a cringe a bit. Digging a bit deeper, it turns out ‘Support of the Cuban People’ doesn’t necessarily mean a tour group, just a jam-packed itinerary that shows you are in fact, doing activities that support the Cuban people.
CREATE AN ITINERARY
In order to create this itinerary, I used ViaHero, a service that connects you with a native Cuban who customizes a plan for you based on what you want to do and see in Cuba. Your plan for each day is then placed into an official-looking document in case anyone asks. My “hero”, Elvy, was great at setting up tours, arranging transportation to and from the airport, and making restaurant and casa particular (basically like a Cuban version of a bread and breakfast) recommendations, and he even partied with me one night!
Elvy would send suggestions for experiences that encompass all aspects of Cuban history and culture and then would let me pick and choose what I thought sounded the most interesting. This was a great alternative for anyone who doesn’t want to be part of an official tour group. Remember to allow enough time for communication with your “hero” as internet in Cuba can be spotty at best, which you’ll learn all about when you get there.
Another important thing to note is that Trump created a list of places in Cuba that are government-run and, therefore, illegal for Americans to do business with. A lot of places on this list are hotels and restaurants. Booking accommodation through Airbnb or booking a casa particular are great ways to avoid potentially staying at a government-controlled place. All the restaurants Elvy recommended to us were deemed safe. I started planning my itinerary in early August to get ready for a late October trip.
FLIGHTS TO CUBA FROM AMERICA
Being from NYC, I had many options when it came to direct flights into Havana and decided to fly JetBlue. In the weeks preceding my trip, I received a couple of slightly scary-sounding emails from the airline regarding the travel sanctions. These emails made me a little nervous, however, there turned out to be more bark than bite. You might have heard of needing to purchase health insurance when traveling to Cuba. JetBlue includes this with the purchase of your ticket.
AT THE AIRPORT
I was told to arrive at the airport at least three hours early (which was not fun for a 9:30 AM flight) and to go to a special counter for Cuba travel. I took the three hours in advance thing a little too seriously and was at the airport at around 6 AM- so there was no line. Was I the only one stressed about this?
Approaching the gate agent, I was ready to pull out my itinerary to prove my support of the Cuban people, however, it was never requested. All she asked was which category I was going under so it could be entered into the computer. This is also where you purchase your pink tourist visa for $50. The process was much easier than anticipated and I was left with three hours to kill at JFK at 6:30 AM (I know the airport can be a lawless place but it felt a little too early to go for the wine).
IMMIGRATION IN CUBA
On the plane, two immigration forms are passed around. One is the standard declaration form making sure you are not bringing anything crazy into the country like, you know, live animals (I left my alpaca at home). The form does have a couple of interesting categories that I haven’t seen on other declaration forms. One asks about electronics and another asks about satellite equipment. Just leave both blank as phones, laptops, iPads etc, don’t count, and they mean things like microwaves, blenders, and larger appliances.
The second form is about public health, making sure you aren’t bringing any diseases into Cuba. One question on this form asks your reason for travel. It lists tourism, business, events, and other. Don’t be that American that puts “tourism.” Check off “other” as you are traveling under one of the categories and are not there for purely tourist purposes. Hold on to these forms because you’ll need them when you get off the plane.
The first stop when you arrive in Havana is immigration. Once again, I felt myself getting nervous and had no idea what to expect. The stone-faced look on the immigration officer’s face didn’t help. When it is your turn to approach the desk you hand them your passport and pink tourist visa. The officer asked me no questions about the reason for my visit. They just took my picture, stamped my passport, took half of my visa, and let me through.
Right behind the immigration desk is a group of pretty much all girls working the security scanners you have to put your bags through. Side note here – these girls were rocking tight, short skirts (yup, their uniform) that surprised me a bit as I was expecting Cuba to be more on the old school, conservative side. Maybe this thought stemmed from the abundance of old stuff Cuba is known for. The forms from the plane are then collected and you’re sent on your way.
RETURNING TO AMERICA
Coming home was just as simple. At the airport in Havana, the process at immigration was the same as entering – you approach the officer, get your picture taken, and they take the other half of your visa. Getting to the airport early here will actually be beneficial as there are less gate agents and officers working so things move more slowly.
Upon landing in the U.S, the thought definitely crossed my mind: “what if I get detained?” As my turn came to approach the desk, my heart was definitely fluttering. The officer asked me where I was returning from, I said “Havana.” He scanned my Mobile Pass form, looked at my Passport, and looked at me. After a brief moment of silence, he said: “Welcome home.” So that was that. No other questions asked. That was just my experience, though, as you know every immigration officer is different.
Overall, the experience of traveling to Cuba was relatively easy. Even though I ended up not needing to show my itinerary, it was still important to have. If you are an American who wants to travel to Cuba but is having qualms, just make sure you check all the boxes and have everything in line so that you are traveling legally.
Disclaimer: Please familiarize yourself with the current rules and restrictions on visiting Cuba before booking your own trip. The rules are constantly changing and We Are Travel Girls cannot be held liable for any information used to book a trip found on our website.
Have you ever been to Cuba? If you have any additional tips for our readers or questions please leave these in the comments below.
To receive our articles and reviews straight to your inbox Subscribe Here.
Our Top Places To Stay In Havana, Cuba
- Hotel Nacional de Cuba
- Revolution Boutique Hotel
- Mercure Sevilla La Habana
- Find the best price on hotels in Havana, Cuba
- Sign up to AirBnB with this link and receive a US $35 off your first booking
Read More About Caribbean
- 10 Instagrammable Spots In Havana, Cuba
- 12 Things Not To Miss In Grand Cayman
- A Quick Guide To St John & The Virgin Islands
- Vinales: Suba’s Most Underrated City
We Are Travel Girls Contributor Kim Fenster
Connect With Kim on Instagram
Pin For Later
This website is a free resource and to keep it free for our readers we may use affiliate links in our articles. If you make a purchase via the links on our site you will pay the same price, but we may receive a small percentage which helps us to keep bringing you new and informative travel content every day! Any products we endorse we personally use and love. Please see our Disclosures for more information.