If you haven’t noticed, Cuba is one of the most popular travel destinations for the year. Since taking a Caribbean Music course in college and being a lover of history, I’ve been wanting to visit the island. I’ve asked friends, read several blog posts and even joined Facebook travel groups to be informed of what to do, where to stay and what to eat. Since it’s much easier to travel to Cuba vs years past, here are five tips if you’re planning a trip to go.

Check Entry Requirements

First things first as an American, traveling to Cuba for tourist activities are not allowed. Before planning, check to see if you fit in one of the 12 categories of travel issued by the Department of Treasury’s Office of Foreign Assets Control (OFAC). As a travel writer, I had the ability to select ‘journalistic activity’, but since my cousin was coming with, we chose the “people-to-people” category. In addition to our personal belongings, we brought clothing and household items to give to our hosts and danced salsa with locals in Old Havana. You can view the full list of categories & current facts about visiting Cuba on the Travel.State.Gov website.

As of June 16, 2017, the current US Administration announced individual “People to People travel” would no longer be allowed. Per the Treasury Dept/OFAC, changes will not be effective until it issues new regulations in the coming months. Individual travel under the support for the Cuban people and other categories will still be allowed.

Get a Visa (Tourist Card) & Cuban Health Insurance

After determining you’re eligible to travel to Cuba, you would need a Visa (Tourist Card). This can be purchased at departure airport for $50. When filling out the card make sure to not make any mistakes lest you purchase a new one. Cuban Health Insurance guarantees your visit to a doctor in the event of sickness or injury. For our flight with Delta, there was a stamp on our boarding pass showing proof of the health insurance. Two blank pages are required on your passport for entry/exit stamps.

 The Government of Cuba treats U.S. citizens born in Cuba as Cuban citizens. If you are born in Cuba after January 1, 1971, you must travel with a US passport AND Cuban passport to gain entry.


Bring cash and make sure you know how to budget. Your U.S. credit and/or debit card WILL NOT WORK. Depending on the market, you can exchange your dollars for Euros or CAD (Canadian dollars) to avoid the 10 percent fee for U.S. dollar conversions.

Getting There

Great news! You don’t have to travel to Canada, Mexico or other Caribbean islands to travel to Cuba anymore. If you’re already in these locations, by all means, travel from there, but there are commercial flights with US airlines available. Here’s a list of US Airlines providing services to the island and the destinations:

  • Camaguey – American Airlines, Jet Blue
  • Cayo Coco – American Airlines
  • Cienfuegos – American Airlines
  • Havana – Delta, Alaska Airlines, American Airlines, Southwest, Jet Blue, United
  • Holguin – American Airlines, Jet Blue
  • Santa Clara – American Airlines, Southwest, Jet Blue
  • Varadero – American Airlines, Southwest, United

You can also visit Cuba from the US via cruise. Below are cruise lines leaving from the US to Havana and other ports of call.

WiFi & Phone Calls

If you need to connect to the internet, wifi is available at specific hotspots and hotels. You need to buy wifi cards and they cost between 1.5 and 5 CUC depending on the length of time purchased. Calling home or abroad is very expensive and it is not possible to use Skype or FaceTime. Instead, use Facebook Messenger and Whatsapp. Another popular option is IMO, another messenger service that runs well with the slow connection. Had I traveled to Cuba alone I would’ve purchased a wifi card, but my cousin and I accounted for each other well.

Over the Memorial Day weekend, we stayed a total of 6 days between Havana and Varadero. We faced good and bad experiences, but it was still a memorable trip. Make sure to check back next week as I share more about our visit including lodging and transportation options.

5 Tips for Planning a Trip to Cuba

Have you been to Cuba or are you planning to visit anytime soon?

58 comments on “5 Tips for Planning a Trip to Cuba”

  1. Looks like it could be an interesting trip. Thank you for all of the helpful hints about visas, currency, etc. I’d like to go to Cuba some time. I am a journalist so that could work.

    • No problem. The insurance is usually a stamp on your boarding pass. Just make sure to keep it with you on the duration of your trip, otherwise it’s about 10 CUC a day.

  2. I have heard a lot of mixed reviews about Cuba. I am still definitely interested in going, but I’m wayyy too spontaneous and don’t trust myself yet. If I can get through my next two trips and stick to the itinerary and budget, maybe I’ll allow myself to plan for Cuba. lol

    • I thought I’d be bad with the budget, but with local drinks between 1 and 3 CUC’s plus lodging already paid for, we did pretty good with money. Some tours, transportation and if you want wifi is the big expense imo

  3. A friend of mines is going to Cuba in September and I was really concerned about her going… but she said the same great things you have written and I think I might get me a ticket to go too… Don’t want to miss out on a mission!

  4. You’re right! It looks like Cuba is the travel destination of the year! I have had concerns about visiting, but with your tips and experience I am def willing to reconsider. I think it’s cool that you can now fly from the US instead of having to travel through Mexico (or a Caribbean island) to get there now.

    Thank you for sharing so much helpful information, JoAnne! You’ve covered ALL the bases! Such great tips, love.

  5. Great tips. I see so many people taking trips to Cuba. I hope this tourism increase is beneficial for the regular population.

  6. I hope to visit Cuba to trace my family history. We are from Jamaica but we have ancestors from Cuba. Thanks for the tips.

  7. I keep seeing recaps of Cuba trips and now I want to go. 45 is trying block that so I guess I need to hurry up before it is nolonger a thing. These tips are helpful as I had no idea where to start.

  8. Once the Cuban ban lifted several of my friends have traveled there and loved it. I would love to visit Cuba one day too.

  9. I was just in Cuba for the month of April! I loved it! As an American your tips are very helpful, but I ended up avoiding all of that because I was in Mexico prior to flying to Cuba!

  10. This was so helpful! I’ve been throwing around the idea of going to Cuba for awhile, but haven’t actually looked too much into it. I feel like this is a sign. Thanks for the info!

  11. I would love to eventually travel to Cuba; I have an aunt from there who has always talked about how beautiful it is! Thank you for the compilation of information; definitely saved me a lot of Googling!

  12. Cuba looks amazing! I’ve been wanderlusting after so many gorgeous photos and your post has just added to this. I had no idea it was so hard for an American to get into Cuba and that even your cards won’t work! I wonder if this is the same for other countries.

  13. This is great information! I wasn’t aware of the airlines that went to specific spots. I am planning on visiting Cuba in the future. Thanks for sharing

  14. SO excited it will be easier to get to Cuba next year. I know the tourist visas are still limited, but I can’t wait!

  15. We visited Cuba before the sanctions were lifted. It was a wonderful trip but you really do need to have great tips like these to ensure a good trip. All of your tips are spot on.

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