Being in Key West at Christmas and only 90 miles away from Cuba, was just too tempting. Should we go? Do we have the time? When faced with difficult decisions on this trip, we have a family meeting and ask ourselves a few questions…
“Is this something we as a family (or our kids individually) would ever likely experience again?” (If no, then do it now.)
“Will this shape us as people?”
Well alrighty then, let’s go to Cuba!

Chick-fil-A was the last American meal of choice. 🙁
Americans can travel to Cuba?
Yes, but it is a little tricky. I learned that there is really only one way for Americans to get into Cuba and that is by claiming Support for the Cuban People. Then when traveling in Cuba, Americans may not patron any establishments related to or owned by the communist government. This includes hotels, restaurants, tourist attractions, etc. You must keep receipts for every transaction made and keep them for 5 years following your visit. Oh, and your cell phones and bank cards will not work. So bring enough cash. And you can’t exchange money at the banks or hotels (government owned) so you’ll need to use street vendors. There’s internet (since 2019) but the government controls it, so you might not be able to access certain sites. Only eat at well established restaurants because the cholera outbreaks are for real and even Cubans boil all their water. Lastly, expect rolling power blackouts daily.
So it was going to be a bit complicated… 🙂 But doable. To help us maneuver all this, we decided to work with a travel agency and hire an English speaking travel guide. We were excited but nervous…
To be clear, we didn’t own any travel gear (duffle bags and travel toiletries had to be bought) and we didn’t own any clothes suitable for visiting Cuban evening clubs – dresses for women (and shoes) and Cuban slacks/pants and a shirt for men. And we needed to figure out a safe place to park RV while we were gone (we left it in a Miami campground and prayed no one would steal the bikes off the back).


Girls urgently try and find some dresses at Ross before we leave!
The American government did what?
Two days before our departure, America takes the Venezuelan President hostage. Such bad luck. And I soon learn that Cuba and Venezuela have a strong alliance. 32 Cuban guards were killed in the attack. Oh my…. this cannot be good. I’m not gonna lie, I was nervous and questioning whether we should take this trip. The thought of getting trapped in a communist country with anti-American sentiment was terrifying. And, we’d be potentially putting the rest of our RV trip at risk. So we sat down as a family and asked ourselves the decision making questions again…
Well alrighty then, let’s go to Cuba!

And we are off! it was a quick 40 min flight.
We were picked up at the Cuban airport in fashion. In very fancy vintage cars!


As you will see in our photos, there are a ton of classic cars in Cuba. The nicest ones are own by private individuals who have painstakingly restored them at significant personal cost. Most of the nicer ones are used for taxi service, because they can make good money off of tourists. That’s our tour guide Lily in the front car – she was incredible. So well educated and smart. She made the depth of our experience 100 times what it would have been otherwise.
Here is a row of parked taxis – for all your car buffs.

Lane takes a front row seat riding into Havana.

The drive into Havana was stunning. The buildings are beautiful (although decrepit) and the Cuban people are even more beautiful. It was both eye opening and breathtaking to see the collision of 3rd world (under developed Cuba) and the 1st world Cuba collide. People hand carrying bags of onions on their backs, horses pulling carts, vintage cars, derelict city buses, and occasionally even a newer car would drive by. We learned that 2 years ago the government started importing some cars. They can be bought by the Cuban people, but they cost the market price of the car plus that same amount again in government in taxes – twice what it would cost anywhere else. Way too expensive for most of the population. Our guide Lily sighed and she explained how the economics worked.
I took the picture below because we saw the red truck coming down the road and were amazed – it was really the only modern pick up truck we ever saw. But I love how this picture captures so much variety in a single shot.

By far the most common mode of transportation for most people in Havana were the 3 wheeled motorcycles. The majority of the population does not own a car.


Our first night in Havana, Lily took us to a Jazz club to listen to music. It was fun and the kids enjoyed the first of many mocktails to come!

Lane even got called up to help make some music!

The next morning our beautiful taxi showed up again to take us on a tour of Havana. Our guide Lester was incredibly proud of his car and loved showing it to Rob and Lane. He had refurbished it entirely himself over time – ordering parts through a black market. Across the street (to the right in the photo), you can see Cubans going to work. The house across the street from our casa was an education administration building.

We stayed at a private casa which was the downstairs floor of this cute little building with awnings. Two sweet ladies would arrive each morning to make us a delicious breakfast – fresh squeezed guava juice, scrambled eggs, mini sweet pancakes, and yogurt. Oh and Cuban coffee – my kids apparently now love coffee!

And we learned very quickly that the rolling blackouts were for real. Each day in the late afternoon, the power would go out for several hours. This was usually about the time we were getting back to the casa two wash up and rest before dinner. Playing cards by flashlight became our blackout activity!

A memory of a lifetime…
I don’t have any pictures to represent this, but in the casa, for the first time in forever, our kids had rooms and beds to themselves. They were over the moon at first. But then a crazy thing happened. All the kids were constantly in our room, laying on our bed, wanting to snuggle (or wrestle in Lane’s case), talk or just hang out. Rob and I were beside ourselves. Here we were in a big house, yet we were all choosing to be crammed in a single room again? We kept telling them to leave and they kept coming back. Finally, as a family we all lay on a single bed and laugh together about how ridiculous this is. It will be one my fondest memories ever and I truly believe it is a product of this RV trip. Most days we don’t get the choice whether to be together or not. It is not always easy. But when we do get a choice, we still choose each other.

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