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Cuba Itinerary

How long was your stay?

5 Days

How did you travel?

As a family

Tell us why you traveled to this destination.

We decided to go to Cuba because how often can you go to a socialist country? We were also traveling with my parents and it’s on my dads bucket list. With our new democratic president, restrictions were lifted once again, and we thought it was a good opportunity to explore a country that most people overlook.

What was your itinerary?

Day 1: Traveled to Old Havana
Day 2: Went to Havana Dance Company
Day 3: Visited Varadero beach
Day 4: Explored Las Terrazas
Day 5: Went to Finca Vigia

Give us all the details! Tell us where you went and what you did on your trip.

Day 1: We worked with an agency because we had to have a cultural visa. We stayed at the Gran Hotel Manzana Kempinski. It was a luxury hotel with all the amenities. Our first dinner was at the Ivan y Justo- a great spot! We had a private cigar and rum tasting. Everyone tried except for the 12-year-old! The first full day we went on a walking tour of old Havana and stopped at a local preschool run by nuns. We brought lots of school donations and played with the children. We stopped at a few local shops and spoke with a lot of the locals.

Day 2: The next day we went to the Havana Dance Company where we got a private performance by the members who are trained dancers and percussionists. The next day we spent the day at Varadero beach. A relaxing day in the sun was a good break. We went for drinks that evening at El Floridita. A must-see in Havana, home of Heming ways favorite bar.

Days 3-5: The following day we were scheduled to go to Las Terrazas, but due to the hurricane, roads were not accessible. Instead, we started our day with a classic convertible car ride. Cuba is filled with old cars from the ’50s. Feels like you are in a time warp! We had a professional photographer follow us on our drive – felt like we were celebrities with paparazzi! We then went to Finca Vigia, home of Ernest Hemingway, which has been kept immaculately intact. We then went cigar shopping- but turns out you can’t bring cigars back to the US. The government still has a strict trade embargo on Cuba. No ATMs, no use of credit cards. Can only use local currency, but my dad was insistent on getting cigars- so he smuggled some in… After all, who is going to stop an 85-year-old man? Glad to report he cleared customs as my children anxiously watched!

Would you recommend this trip to a friend?


What was the highlight of your trip?

The highlight for me was going to the local preschool and donating school supplies. It happened to be Christmas so we were able to see the kids perform in a choir concert. We gave each of the kids a gift bag, and the nuns were very appreciative of the three extra large suitcases filled with school donations that my friends from home had so generously given me. Also, a highlight was learning about modern-day Cuba from a local perspective. It was fascinating, and information that we can’t read in a newspaper or view on a website. Speaking to the younger generations about their frustrations with the government, and their personal experiences trying to be an entrepreneur in a socialist government makes you appreciate capitalism and democracy in the USA!

If you were to take this trip again, is there anything you would add or do differently?

Honestly, I would probably not bring my children. A cultural visa was required so we had to do a lot of cultural activities and tours. While I appreciated it, my kids generally are not tour guide people. We travel the globe extensively and like to be active and find some hidden gems, but we had a strict itinerary and often were doing things that felt a bit too touristy. I would definitely try to balance tour guide with self-exploration! I would also bring more items to donate. Our hotel doorman told me his son was in medical school, and did not have access to a stethoscope or an oximeter. I would bring so many things that we can easily purchase on Amazon! We did leave everything behind from our backpacks to our Toiletries to our remaining US dollars.

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