How To Travel To Cuba With An American Passport!

May 16, 2016

DSC09257 DSC09364

Unless you’ve been living under a rock somewhere, you already know that travel to Cuba just got a little bit easier! That being said, fifty shades of grey has nothing on the cloud of mystery weighing over the ‘how to’ of traveling to Cuba as an American. It seems as though no amount of Googling will provide a stitch of lucidity to this topic. I’m not one for breaking domestic or international laws (my mama might be reading this) so trust me when I say, I searched. So prompted by various smoke screens, I decided to go out and do it myself! This is in NO WAY a bonafide expert guide, but it’s definitely how I traveled to Cuba with an American passport.


Step 1. Choose your travel category. As an American, vacationing and touring in Cuba is still not permitted. However, you can now go to Cuba legally without a license or paperwork as long as your purpose of travel fits under one of these U.S. government approved categories. It seems to operate on an honor system but I officially chose journalistic activities. The only time I was asked about this category or why I was visiting Cuba, was when an immigration officer in the José Martí (HAV) airport took a special interest in me and my friend Lo. This was not a big deal, she seemed a little more interested in what we were wearing than asking us official questions!


Step 2. Choose your departure city. I live in New York City, so this one was a pretty easy decision for me. Obviously, your departure city will dictate the expense of your flight. For example, as of today, flying out of Boston is cheaper than flying out of New York City. Flying out of Los Angeles and Miami seem to be more economically friendly as well. And as for flying out of Canada? With those price tags? That’ll be a solid nope from me.


Step 3. Choose an itinerary. Read carefully because some of these itineraries have rather long layovers. Copa Airlines and AeroMexico are two airlines that can be used to get to Cuba via other countries. I wanted to optimize my time, so I booked a flight to Cancún, Mexico then a separate flight on Interjet Airlines to Havana, Cuba. THIS IS NOT ILLEGAL! However, my first experience with Interjet was a bit of a nightmare. Let’s just say all the reviews that can be read on the innanets are true!


Step 4. Buy your ticket. YES, YOU CAN BUY YOUR OWN TICKET! Apparently, in the past, this was not always the case. Travel search engines such as Google Flights, Kayak, SkyScanner and the like allow you to buy flights with layovers in other countries. All DIRECT charter flights from the U.S., mostly from Miami and New York City,  are to be purchased through an agency. Fingers crossed, direct commercial flights are to become available later this year.


Step 5. Get on your flight. I passed through TSA without any issue. No one flinched or batted an eyelash when I was asked about my final destination. I wasn’t given any trouble in Cancún either. Everyone must purchase a Cuban Visa at your departure airport. I paid $20 U.S. dollars in Cancún for one. Half of it was taken when I arrived in Havana and the other half I handed over upon departure.


So there you have it folks, in a nutshell, how I traveled to Cuba with an American passport! If you have any specific questions, please leave a comment below and I will do my best to answer to the best of my knowledge. Other than that, I’ll be rolling out posts on WHY you should put this amazing country on your radar!

Where: Havana, Cuba

Dress: Zara

Shoes: Asos

Bag: J. Crew


  • Bianca @itsallbee

    You look super cute! I love the pictures. I cant wait to visit Cuba. Hopefully I can make it there end of the year.

    • admin

      Thanks Bianca! I hope all this info helps you get there faster!

  • Maurice @Itz_Jmirr

    I just wanted to ask, what all did the itinerary you guys came up with consist of? And what would you suggest the itinerary for someone going under the general license of educational or support for the cuban people consist of? Also, did you guys catch any heat on the return trip? Like when coming back through U.S. customs? I tried asking Lo yesterday but I think she was done answering questions for people lol

    • admin

      Hello! Out itinerary consisted of a lot of things but mainly the four day music festival, Musicabana. Under a general license, there are many activities in to participate in within the city i.e. dance classes, artist talks, musical performances. These all apply. We were both perfectly fine on the return trip. Hope this helps!

  • Leila

    Your post was so helpful!! I’m currently planning my trip for mid-June and reading your information definitely helped reassure me that I’m on the right track! The pictures look amazing! Love all your outfits! Did you visit Varadero (resort, beach area)?

    • admin

      Hello Leila! Thanks so much! I’m so glad I was able to help you. I will be putting up another post really soon about things you should know once you’re on the ground, so stay tuned! I skipped over Varadero because Playa Santa María is gorgeous and just a 20 minute ride from downtown Havana!

  • Rae

    Hi Modupe! I am absolutely loving your blog! This post is every thing for me because I’ve been so lost in how exactly I should plan for Cuba. I plan on going in August. I have a question, do you think the journalistic opportunity reason would work for someone like myself who isn’t a blogger? I loved how easy going the agent was who interviewed you but I’m a little scared on what to expect. Looking forward to hearing back from you

    • admin

      Thanks so much for your feedback Rae! I chose that category because I am indeed writing and blogging about Cuba. Really not sure if the category is the most appropriate one for you. Did you read the other categories? Can any of those apply?

  • Cynthia

    Your post has been very helpful as I am currently planning to go in July. Question, were there any restrictions when you went to the beach?

    • admin

      Hi Cynthia! There are general restrictions for Americans because tourism and vacationing in Cuba is still not permitted. That being said, no one is checking for you nor is anyone aware that you’re American. Hope this helps!

  • Pearl B

    Hi Modupe,
    Thanks for sharing. Can you share tips on accomodation? I’m heading to cuba next month and have been exploring Airbnb and hotels. Most hotels are not available on my dates.

    Where did you stay and would you recommend it?



    • admin

      Hey B! With regards to accommodations, I stayed at an Airbnb (Villa Sofia) and wouldn’t have had it any other way.I would definitely recommend that you look into grabbing an Airbnb. Hope this helps!

  • Pearl B

    Thanks so much Modupe! Really appreciate you responding and sharing. I have reached out to Villa Sofia.. 🙂

    God bless and looking forward to your next adventure.



  • Ajana

    Thank you so much for your blog! I love sharing in your adventures. Your photography- fantastic. Egypt looks amazing, so I’ve re-added to my must visit list. Cuba is of most interest to me today because I am trying to plan my trip there to see our friends get married there this summer, on top of the fact that it’s already been on my list for years. I’m so glad there’s been a slight shift in US/Cuba relations. Thanks so much for the info on HOW to get there (passport, visas, air), but I’d love to know where you stayed or if you had any recommendations on where to look. Thanks. I’d love to hear from you soon!


    • admin

      Ah! So glad this was helpful. I hope it helps you get to Cuba for the wedding. As far as where I stayed and all that good jazz, that will be coming in a later post. Definitely this month!

  • Rae

    This is really, really helpful. I don’t think I’ll be able to travel to Cuba this year due to trips that I’ve already planned, but this is great information for future reference. I’m starting to incorporate a travel segment to my blog so I think I’d probably fall under the journalistic category as well. I’m sure things will change from now and until the time I will most likely travel. Hopefully that would me I can get a shorter flight from New Orleans to Cuba.

    • admin

      YESSSSSSS! So glad this was helpful to you. I hope you do make it to Cuba next year!

  • Ajana

    I’ve been trying to find Villia Sofia through AirBNB but can’t find her. Do you have more information to locate her? I am trying to go at the beginning of August. Thanks!

  • Monet

    Hi Modupe!!

    Thanks so much for this, I have been searching for a guide on Cuba and this is by far the best! I know these questions are hard to answer but figured I’d throw it out there. I would really like to visit Cuba with my family, including my two young daughters. I have my own blog , writing specifically about traveling with children so I would choose the journalistic category but do you think I would have an issue with customs because of the kids? Any insight you have would be great!

  • Joy

    Thank you for this post.! Just to be clear, you didn’t need to get a visa prior to leaving the US?

    • admin

      Hi Joy! I went through Mexico and obtained it there. Hope this helps!

  • Pips

    This is great, Modupe. I want to plan a trip but really want to make it a solo trip. Would you advice against that since I don’t speak Spanish?

    • admin

      Hello! Definitely take a translation book with you, to get a few words in. I know a lot of people who don’t speak Spanish and had a wonderful time. Let me know if you make it there!

Leave a Comment

All Content © 2014 Let's Go Yesterday. All Rights Reserved.