3 Tips for Traveling to Cuba

How to get there and back without getting fined.


I fell in love with Cuba when I was a teenager. Before I moved to New York City, I went on many trips to Havana with my family. It was one of the few cities that I never got bored visiting. The people are so friendly, the customs are fascinating, the ballet is almost free, and everywhere you look you are overwhelmed by the beauty that surrounds you. I always wanted to go back. But since I’ve been living in NYC (and married to a New Yorker), it’s been impossible. Now, though Cuba’s not quite “vacation-ready” for Americans, we may be heading in that direction.

3 Tips for Traveling to Cuba

Chatting with a local in Havana

3 Tips for Traveling to Cuba

A photo I took of a local entrepreneur and her cat

Since President Obama announced a move to restore diplomatic relations with Cuba and to alleviate certain travel restrictions, American travelers have been anxiously awaiting the opportunity to pay Cuba a visit. This will mark the first time in more than 50 years that Americans have been allowed to travel within the Cuban borders without having permission from the U.S. Treasury’s office. And though many restrictions remain in place, the move still represents a landmark moment for those who want to visit family or who are simply curious about our island neighbor to the south.

3 Tips for Traveling to Cuba

Shopping for art in the square (although Havana has incredible, and inexpensive, galleries)

That said, we’re still swimming in new waters, so prospective travelers need to educate themselves as much as possible before booking that plane ticket. If you’re considering a trip yourself, here are just few tips to help you stay safe and stay legal when planning a trip to Cuba.

Pages: 1 2 3 4

Avatar of Hilary Rowland

A writer, artist, and designer since she was young enough to put pencil to paper, Hilary taught herself code and created Urbanette when she was a teenager. Currently, she lives in Monte Carlo, but spent the past decade living in NYC, still considers herself a New Yorker, and visits regularly. She's always traveling, looking for hot new topics, destinations, and life hacks to bring to Urbanette readers.

Reader Discussion: 110 Comments

  1. Avatar of Jamie Nash

    Will definitely visit Cuba sometime this year. Simply because of the old cars. I’m a huge car junky and really love the classics. Such elegance and slick designs. It’s like a shiny bucket of death. We all know the safety standards of old cars right?

  2. Avatar of Lynn Hayes

    Lynn Hayes

    Cuba is definitely on my list of places to get to soon and this is such a thorough guide! Lots of things I didn’t know. Thanks for putting it together! I actually had a Cuban sandwich for lunch today in Cambodia of all palces, and it wasn’t that great 😉 lol

  3. Avatar of Roberta Bennett

    Roberta Bennett

    This is a really extensive guide! Fantastic post with great info! Planning our visit at the moment. Cheers!

  4. Avatar of Frances Seifert

    Frances Seifert

    This article is so helpful! We are currently trying to figure out how we will plan our trip. We looked into th people-to-people tours, but they seem to be a bit too organized for our taste. The trampoline method could be the best option, but my husband is a bit nervous that something could happen, and we might have trouble getting out of the country if so. Thanks for putting this together… I am going to be bookmarking it to help with our plans!

  5. Avatar of Amanda Roberts

    Amanda Roberts

    What a comprehensive guide to travelling to Cuba. It’s helpful to see the tricks and catches pointed out to help with the planning. Simple things like slowing down and taking extra care with the forms to avoid duplicated costs and non-US based travel insurance are easy things to miss.

  6. Avatar of Kimberly Thompson

    Kimberly Thompson

    I just returned from Cuba a few weeks ago, it was so amazing! Def stay with a local family in a casa cheaper and great experience.

  7. Avatar of Emma Blackwood

    Emma Blackwood

    Cuba is such an enticing and exciting destination right now. I wanna get the opportunity to experience it before massive tourism takes over.

  8. Avatar of Catherine White

    Catherine White

    Great tips! I hadn’t realized that Cuba would be such a gorgeous country. I would really love to visit Cuba someday. Their history and culture sound quite interesting.. Great tips for those who would like to travel there for the first time.

  9. Avatar of Nicky Bryan

    Nicky Bryan

    Thank you for these tips! Thanks Hilary. I have friends that recently went to Cuba and they spent a fortune. I want to make it on a budget, at least I’ll try!

  10. Avatar of Pearl Nguyen

    Pearl Nguyen

    Thanks for the tips! I did not know it was so expensive to go there. Hopefully, I get to go one day.

Load 10 more comments

Join in the Conversation! Leave a Reply

Your email address will not be published. Required fields are marked *

Urbanette moderates and edits comments for grammar and to facilitate an informed, substantive, civil conversation. Abusive, profane, promotional, misleading, incoherent or off-topic comments will be rejected. Please use your full name. Moderators can only approve comments written in English.

All content is strictly copyright. Contact us for permission.