176: Travel to Cuba with kids

Vacation Mavens

Nov 3 2020 • 47 mins

Are you intrigued by the music, food, and culture of Cuba? Find out what it is like to travel to Cuba with kids as we speak to Deborah Haile, author of a series of children's books about traveling with kids.


This podcast is sponsored by Moon Travel Guides. Learn more about The Open Road: 50 Best Road Trips in the USA. All opinions are our own.

00:30 - Talking with Kim and Tamara

08:27 - Talking with Deborah

10:07 - Traveling to Cuba

17:28 - When to go

18:45 - How long to stay

23:19 - What to do

32:20 - Jonah’s Global Footprints book series

38:09 - Final Tips

42:11 - Deborah’s favorite travel gear

43:14 - Where she is heading next


Deborah Haile is the CEO of Tiny Global Footprints and the author of Jonah's Global Footprints book series. She holds a Master of Public Policy from George Mason University and a Bachelors of Arts in Sociology from University of Minnesota. Deborha loves traveling the world with her son Jonah, and sees a world where working moms have the tools they need to be able to make international travel with their children a priority and a possibility. She is originally from Eritrea, but grew up in Minnesota, lived in Virginia and recently moved to Miami. She is extremely passionate about exposing children to global cultures.

Follow Deborah on Instagram.


  • If you would like to plan a trip to Cuba after places start to open up fully, you should know that you can no longer stop there on a cruise trip. You will need to get an Advance Visa. You can get this online or go in person to the Cuban Embassy.  This is only one of the ways that you can travel to Cuba.
  • There are different categories for traveling to Cuba for Americans, which include: family visits; official business of the U.S. government, foreign governments, and certain intergovernmental organizations; journalistic activity; professional research and professional meetings; educational activities; religious activities; public performances, clinics, workshops, athletic and other competitions, and exhibitions; support for the Cuban people (obtaining a Visa, staying at a Casa and eating at local restaurants); humanitarian projects; activities of private foundations or research or educational institutes; exportation, importation, or transmission of information or information materials; and certain export transactions that may be considered for authorization under existing regulations and guidelines.
  • The best time to visit Cuba is between December and May, which is after hurricane season.
  • 7-10 days is a good amount of time to give yourself to explore and take in what some of Cuba has to offer.
  • Start in Havana and then rent a car to travel to places like Vinales or Varadero to experience more of Cuba.
  • Keep in mind that you will have limited access to WiFi when in Cuba. This is a great opportunity to disconnect and immerse yourself in the culture around you, but you also need to be prepared.
  • English is not widely spoken so if you are not a fluent Spanish speaker, you may want to brush up before your trip and look into a language program to teach yourself some basics in order for you to get around easier.
  • Be aware that not all U.S.-issued credit cards will work in Cuba. Be sure to bring along plenty of cash, because finding an ATM can also be challenging in parts of the country.
  • Packing light will make getting around that much easier, and you won't need much while you are there.
  • Be aware that those cool old cars you see around Havana don't have seat belts. Plan accordingly if you feel you will need a carseat for your child on longer drives.
  • You should also do a lot of preplanning for your trip before you leave. Since you will not have easy Internet or phone access, you will want to bring printed maps and information for the places that you are staying. You might also want to think about bringing a Spanish-language dictionary or printing up some phrases to help you with your travels.


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