Legal Travel to Cuba for Americans and Why NOW is the Time to Go!

Legal Travel to Cuba for Americans

Cuba is slowly opening up to Americans. Contrary to popular belief, Americans can go to Cuba and do so legally. I’ve asked fellow blogger and Cheesehead Heidi Siefkas to give an overview for how Americans can travel to Cuba and why they may want to consider doing so now.

When I told my friends and family that I travel to Cuba, I receive many questions, all with puzzled looks. Many ask if it is legal. Others ask if it is safe. Others wonder why travel to Cuba at all. Having five trips under my belt this year alone as a tour director and four more trips this fall, I have fallen in love with Cuba, its people, and cultural richness. Although Cuba is not on the traditional traveler’s radar, I would like to share with you how you too can travel to Cuba. So here’s the skinny on legal travel to Cuba, how it’s done, and why you should travel to Cuba and NOW.

How can Americans travel legally to Cuba?

Legal Travel to Cuba for Americans

First, let’s get the truth out there. Cuba doesn’t prohibit Americans from traveling to Cuba. It is the U.S. government that limits travel to Cuba. Per the Treasury Department, Americans can travel to Cuba with a license from its Office of Foreign Asset Control.

So if you want to travel to Cuba, how do you get one of these precious licenses to travel to the forbidden fruit of the Caribbean? There are three legal ways to travel to Cuba. Since many of the readers here will not fit into the fairly limited categories of journalist, full-time academic or research professional, or a person on official governmental business, I’ll skip to the way most Americans who want to experience traveling to Cuba can choose.

The most common legal travel option for Americans is through the “People to People” programs.

President Obama recently opened the “People to People” travel option for Americans who don’t qualify for independent licensing explained below and wish to visit Cuba on an educational tour. The tour operator is responsible for leading a tour that meets the “People to People” itinerary, which is very interactive and educational in nature. The tour operator is the entity that holds the license and adds the passengers to that license for a particular range of dates. This license is given to all participants and must be carried with the group for passing through customs.

The itinerary has a full-time schedule of three or more “People to People” interactions a day over the traditional nine-day tour. The activities touch on a wide range of topics from Cuban cooking to a political discussion with a former Cuban diplomat as well as musical performances including classical, jazz, and contemporary music. Yes, there are many activities a day, but there is plenty of time to enjoy Cuban rum, cigars, and even free evenings to enjoy private restaurants, jazz clubs, and the like. To see examples of tours to Cuba as well as prices, check out Road Scholar and Insight Cuba.

The flights to Cuba with these “People to People” tours are direct from the U.S. Most fly out of Miami or Fort Lauderdale into various cities in Cuba. My experience is with flights into Cienfuegos, Santa Clara, and Havana. In little under an hour, the “People to People” travelers have crossed the 90+ miles and will have time-traveled over 50 years without the help of the Back to the Future DeLorean.

Other ways to travel to Cuba legally, but with strict categories:

Legal Travel to Cuba for Americans
  • If you are a professional journalist/photographer on assignment, a full-time academic/research professional conducting a study or attending a conference, or a person on official government business a general license may be granted to you from the Office of Foreign Asset Control after meeting its requirements. You must apply, providing ample detail of your goal(s), itinerary with activity descriptions, organization/news source, and duration of trip. As each of these categories requires different information and specific guidelines, please review the requirements with the Office of Foreign Asset Control (Recommended 45 days prior).
  • If you are a person visiting immediate family, a full-time graduate student conducting academic research to be counted toward a graduate degree, an undergraduate or graduate student participating in a study aboard program of at least 10 weeks in length, a professor/teacher employed at a U.S. institution traveling to Cuba to teach, a person engaging in religious activities, humanitarian projects, non-profit cultural exhibitions, or a freelance journalist, you will need to apply for a specific license with the OFAC well in advance of your travel (Recommended 45 days prior).

These options would allow for you to travel without a group. However, the planning is up to you. I would suggest looking into a Miami and Los Angeles based company Cuba Travel Services that assists travelers with the application process for licenses, visas, flights, and arrangements in Cuba such as accommodations, tours, and more.

So, Why Should You Travel to Cuba and NOW?

As I alluded to, a trip to Cuba is like traveling back in time. The mixture of a simple pace and lifestyle with the colorful 1950’s cars parked in front of colonial and neoclassical architecture is just the beginning. Traveling to Cuba is an experience of sensory overload with smells and tastes of the true melting pot of Caribbean. Plus, the creativity of Cuba is abound; everyone is an artist whether a musician, dancer, painter, or poet.

With changes in the government and Raul Castro’s appointment in 2006, the country is progressing rapidly. Only a few years ago, Cubans were allowed to have cell phones. Granted they aren’t Smartphones, but it is common to have a landline and cellular. Likewise, the Internet is becoming a bit easier to find, mostly in offices and hotels. Over my last trips, I’ve noticed changes such as the opening of direct mail from Cuba to U.S. without a stop in a third country as well as a change away from the array of different colored license plates signifying governmentally owned cars vs. privately owned cars. I can attest that the entrepreneurial spirit is evident through the growth of paladares (private restaurants), private movie theaters, invite-only house parties in private homes, and private tour guides.

Of course there are rumors that someday cruises will come to Havana’s port; thus, the transition of the industrial parts of the port are underway and moving to a nearby town, Mariel. Before cruises come to Cuba as well as more open travel from the U.S., you must visit. Discover some of the unforgettable parts of Cuba from my last trips:


Legal Travel to Cuba for Americans

All I can say is that one cannot or at least should not go to Cuba without taking a ride in one of these splendid 1950’s cars. With a bouquet of vibrant colors from purple to pink and metallic, these cars are a wonder, a wonder as to how they are still running. With the shortage of parts to repair these cars, most owners are very good mechanics taking parts from Russian cars or other makes to jerry-rig the cars to continue to drive them. It is a running joke in Cuba that the other name for a Cuban mechanic is a magician. I have seen firsthand that when you have a car that doesn’t have a speedometer that works or a gas gauge well you have to improvise. I guess it changes the “if it ain’t broken, don’t fix it” into “if it’s broke, but you can still drive on without it; go for it. It’s not that bad.”


Legal Travel to Cuba for Americans

The Cuban cuisine is a mixture from all of its influences from Spanish and the colonial times to the African slave influence. The most traditional meal that is made for birthdays and of course the number one national holiday on New Year’s Eve to celebrate the triumph of the Revolution would be a roasted pig. The roasted pork in Cuba is fall off the bone, juicy, and certainly not spicy. Although many think that Cuban cuisine would be spicy, there are very natural flavors used throughout to enhance, but not overpower. You will see a lot of lime, salt, some garlic, and a concoction that uses them all called mojo. A typical side dish to accompany the roasted pig is a rice and bean dish that is called Moros y Cristianos (the Moors and Christians) to signify the colors of the rice and beans.

¡Qué rico!


Legal Travel to Cuba for Americans

When in Cuba, do as the Cubans do, which means rum. The mojito is the most traditional with mint, sugar, soda water, lime, and rum. However, a good blend of America and Cuba is the Cubalibre that was developed when the U.S. Marines were in Cuba at the turn of the 20th made with rum, lime, and coke, but in Cuba that wouldn’t be Coca-Cola, but Tu Kola, similar in taste, perhaps sweeter. Another libation that most don’t know about is the canchánchara, which is the typical drink of the city and region of century. The drink is refreshing and sweet Trinidad. The rum, honey, lime, and soda water cocktail is served in a regional clay cup with a stirring stick for the honey. It’s sweet, but it has a kick.

For those that want to try Cuban beers, there are two front-runners: Crystal and Bucanero. Crystal is a lighter, traditional beer; whereas, Bucanero is a stronger, darker beer, but certainly not as heavy as other ales. The saying goes that Crystal is more suited for women and Bucanero for men, but I’ve pushed the gender limits and tried both ¡Salud!


Although Cuban music probably grew in fame tremendously after the release of Buena Vista Social Club, the country is full of musicians, dancers, artists, and just plain creativity on overdrive. There are some of the best jazz musicians that I have heard in Havana. I highly recommend the Gato Tuerto (one-eyed cat), which is located near the Hotel Nacional with a restaurant upstairs and jazz club below. It doesn’t get going until 10pm, but the music and vocals are right up this jazz cat’s alley. Also, if you want another option for an instrumental jazz location, I would suggest the La Zorra y El Cuervo (the fox and the crow). You can’t miss the door, which is marked by a traditional English telephone booth. Lastly, I would say that the Taberna Café in Havana Vieja has a good Buena Vista Social Club interactive show. It is a bit touristy, but they serve up some sharp musical chops along with three drinks during the show for the patrons. Let the mojitos, Crystal, or other flow.


Legal Travel to Cuba for Americans

Cuba is known as a photographer’s paradise, mostly because of the vibrant contrasts. With its architecture, it is no different. Throughout the country whether in the city of Trinidad, which has remained in the times of the sugar barons, to Havana, which struts the era of opalescence and recently restored buildings along side others in ruins, it’s a visual surprise around each corner. As an amateur photographer, I hope my pictures of the architecture, cars, food, and drink do justice to Cuba. If not, I challenge you to take a trip to Cuba and see for yourself.

If you have any questions about travel to Cuba, recommendations, and/or comments about your travels, please fill free to contact me on my blog or on Twitter @HeidiSiefkas

Heidi Heidi Siefkas is a freelance writer with a passion for adventure and cultural travel appropriately nicknamed Ms. Traveling Pants.

25 thoughts on “Legal Travel to Cuba for Americans and Why NOW is the Time to Go!”

  1. sounds crazy to some but to way sane just makes me me nuts that cuba is closer to me than Atlanta lol been there don that if you get this sos minus the vodka bottle lol non Russian clue me live in norh east cool village gay community.. so ready for change I was one of those hide under ypur school desk kids oops was that the bay of pigs????? Moscow /Havana/paris/la/jax/ oops stick to the subject HAVANA really want to get therer fast gay marriage is great change is in my blood ……. save cuba is or should me a montra not a southbeach suburb,, long live CUBA daddy castro we love your paradise hopefully native Floridians will with all due respect your homelad and its rightfull position as the aqua marine jewel filled with the love and kindness my grandmother shared with me following her well earned vacations to what she passed to me as her days in paridise… my typing sucks BUT to me that shall all ways be cuba my soon hopefully to be homeland proudly so might I add

  2. I want to go to Cuba to visit some friends is it possible. I am a bilingual teacher and I would like to know about their education.

  3. With the latest info that I have been hearing in the news, Please confirm if it is safe to travel from the US to Cuba. I have clients that wants to vacation in Cuba.

  4. Um there alot. May go rent for awhile.
    Any info about phoning there, anyone i can call wpupd be teriffic
    Sometimes i feel islated about k owing these kind. Thgs.
    I now havre “family” there
    If YOud like info pls feel free to contact me
    Here niw

  5. Great information! As a Cuban born I can fly to Cuba with a visa and take my family with me. We visited two years ago and it’s definitely worth the trip. The people are very friendly and go out of their way to make your stay welcoming. The only way for Americans to travel is either going thru a different country (as long as you’re not from Cuba) they will probably let you in. Or booking a tour that is educational, religious etc. These are quite expensive for the average person. I have a trip plan for March to go back.

  6. Thank you for all the information! My family’s looking at going to Cuba in May/June, so this was very interesting to read.
    Is it just the US government who places limits on travel to Cuba or do other countries as well? And if you aren’t from the US, but would be flying from the US, would this place a limit on the travel also?
    Looks like we have plenty more research to do, but judging from the photos of the cars/architecture/cocktails it definitely seems worth it!

  7. I have heard that Cuba is changing almost daily. I think that it will inevitably be open before long. Great tips here.

  8. Love to see Cuba getting some more recognition. It’s a fantastic place, and a bit misunderstood and under-appreciated here in the US.

  9. I would love to visit Cuba. The Cubans I have met have all been very friendly and the food is great. They are letting ne cars in now, so I need to hurry up if I want to see those old classics

  10. As a Canadian, my fellow citizens (and soon, me!) have enjoyed unfettered access to this unique country … it truly is an intriguing place in its current state, but it won’t last since the embargo is beginning to thaw.

    Go now, my American friends!

  11. Cuba is fantastic. Now is the time to go before it truly opens up and becomes like everywhere else in the world. Right now, visiting Havana is unique experience you’ll never forget!

  12. Cuba looks and sounds awesome! I have just added it to my travel wish list! I have to go and see for myself! Thanks for sharing, and love your photos.

  13. Actually when visiting Cancun a few years back, I met many Americans who travelled to Cuba legally with their US passport. The way to do it, they told me, was to get the Cuban stamp placed on a piece of paper that was stapled into the passport. After returning to Mexico, they simply ripped the paper out and the US government never knew they actually went…

    I would imagine it still works this way, especially because, as you mentioned before, Cuba itself has no restrictions for US citizens…

  14. Awesome post! I for sure want to go to Cuba, but I worry about the cost for these programs. I think it is probably a bit more expensive because its a more guided tour. People to People tours may be a much more intimate, personal experience, too, which may make it worth the cost. Usually I couchsurf to get the opportunity to engage in the local customs and learn more about the country, but I doubt that is possible with the visa regulations in the US for Americans traveling to Cuba!

    Thanks for the great post!

  15. A really interesting article. I didn’t think Americans could go to Cuba. All I knew is that as an Australian I couldn’t get to Cuba from the US – or I didn’t think I could! My Aussie friends went last year and loved it. It looks like a great place. Good article.

  16. Still waiting for someone to explain to me why it’s ok for Americans to travel to Iran, but not Cuba. I guess it will be that way as long as Florida has electoral college votes.

  17. Cuba is indeed a trip back in time… and if it opens up more to the rest of the World, I’m afraid the hidden gem might get ruined.

  18. A small correction to a very useful introductory post. There is some confusion between specific license and general licenses. Specific licenses are those that are applied for, including for people to people groups. General licenses require no application, e.g. for Cuban Americans, university faculty led programs for credit (one or more weeks), and religious organizations.

    Our goal should be to obtain general licenses for all purposeful travelers so everyone has the option of group tours or going on their own as Dave suggests,but legally. More here

    Quickroute and others with Irish roots might consider this unique window:

    John McAuliff
    Fund for Reconciliation and Development

  19. I couldn’t agree more, go go go, soon! I just returned from a two-week tour of Cuba. I chose an organized tour but if your Spanish is very good you would manage. However, the people to people experiences gave me an understanding of the people, culture and ideology of Cuba that traveling independently would not have done. Cuba deserves an in-depth exploration.

  20. I am a US Citizen and traveled to Cuba via the Bahamas back in 1998. I am a Irish citizen by birth so used my Irish passport just in case on arrival. Definitely a trip back in time so do go now before the gates open up and it just becomes another tacky commercial beach resort with all the frills

  21. All the people to people tours I’ve seen are very expensive, at least $2,000 and often more. That makes them accessible to a small percent of Americans.

    All the Americans I know who have gone go through the back door via flights from Cancun. That’d be my approach too.

    Tomorrow on my blog, I’m publishing a guest post from a backpacker who said he visited on a budget of about $35 a day.

  22. It has been almost two years since I traveled to Cuba with a small group of Americans. I highly recommend going! I wrote several articles about our time there on my blog for anyone interested in seeing more pictures and a suggested itinerary. Go, go soon. You won’t be disappointed.

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