Simple Tips for a Great Trip to Cuba from Dayna Steele

Last Thanksgiving, we booked an early Spring 2015 InsightCuba trip for the entire family to visit Wonder Husband’s ancestral island. On December 17th, the entire trip and experience took on a whole new facet with these simple words from President Obama, “Today, the United States of America is changing its relationship with the people of Cuba.”

I changed my relationship in regards to Cuba on June 3, 1990 when I met my future husband and eventually married into the Justiz Cuban-American family. I learned to speak louder while other people were talking to make my obviously correct point-of-view heard above the fray of family members all doing the same. I learned to play Cuban dominoes and to always try to be on my brother-in-law Ralph’s team. I gave up learning all but the most important Cuban words in the family, some of which I can’t repeat here. I learned to eat and cook arroz con pollo and a mean pot of black beans. Unfortunately, I still dance like a white American girl. 

As a “Cuban by marriage” and a giddy InsightCuba customer, here are the questions people will ask you when you return from Cuba along with my answers to help you decide to go or to help you answer after your own Cuban adventure:


Why did you go?

To beat Starbuck’s and McDonald’s to the island and to finally let my sons touch their heritage. For the food, the people, the music, the sights, the sounds, the smells, and the history. For the cigars. Definitely for the cigars.

Were you frightened?

Not at all. I posted what I wanted, said what I wanted, pretty much went where I wanted, and asked the questions I wanted answered. It’s quite obvious it is still a military state but the times are changing and there is a little more leeway for different voices. The answers I received were obviously skewed towards the party line but that just made it all that more interesting – and at times frustrating. And, I may or may not have lost my hi-speed hotel wi-fi for a few hours after one of my Twitter posts…

Was there food?

I carried tons of snacks for fear I would starve with all the food rationing, etc. I had more than enough chicken, pork, beans, rice, flan, and more to keep me full daily. There is not a huge variety like most Americans are used to but still plenty in the restaurants and hotels. Just remember, food is still rationed for the majority of Cubans in very small portions. Be grateful for what you have while there and for what you have when you return.

Will you get your husband’s family homes back?

I always thought that would be the case, that would be something we would obviously fight for. Now? I’m not so sure. It has been a very long time and generations have been raised in these homes. Generations of very nice people I met and worked with while in Havana. I don’t want to have to be the one that makes that sort of decision.

Is it worth the trip?

Yes, it changed our lives. My sons learned more about their heritage. We met cousins born after the revolution that even my husband had never met, only heard about. Even without the family connection, it would have been an amazing experience. It is history. And, the changes will take a long time but to be able to see the start of something new was just amazing. So many of the Cuban people are just holding their breath waiting to see if this will really happen, what will happen, and how it will change their lives. Again, it is living history.

How did you get there?

We put our entire trip into the hands of InsightCuba and their amazing staff including our guide, American medical student Graham Sowa – who eventually became my co-author of Havana: 101 Ways to Rock Your World after this trip. Even with all the flights opening up, it helps to have an experienced tour company like InsightCuba and a guide like Graham. Rules and laws are changing daily – I felt much more comfortable traveling with someone who knew what those changes were.

Should I go?

Yes. Yes. And yes. Go now to get the full flavor. Get there as fast as you can. I’ll go with you….

I’ll leave you with the Justiz family toast from Abuela Gloria Justiz:


Salud, dinero, y amor - y tiempo para disfrutarlos.

Health, money and love - and the time to enjoy them.


Also read: So we went to Cuba for the weekend (The Huffington Post, March 2015)


Dayna Steele is a popular motivational business speaker, CEO and creator of, and the author of the 101 Ways to Rock Your World book series including Havana: 101 Ways to Rock Your World - available in paperback and Kindle versions from