The Cuban embargo has been, more than anything, a family drama, with the Gulfstream running like an iron curtain through generation after generation of Cuban and Cuban-American families. So while pundits weighed the policy implications of Obama’s December 17 shock announcement of direct talks with Cuba, Cuban-Americans like Edel Rodriguez had more personal calculations to make.

“There was a burst of excitement, an ‘it’s about time’ sort of reaction” he says, “tempered by a wait-and-see attitude. We are dealing with politicians here, on both sides, who say things that often don’t go anywhere. This is probably my family’s attitude in Cuba as well.”

Rodriguez, a celebrated artist and illustrator, happened to return to Cuba this month for the first time since he fled at age nine 34 years ago. He was a Marielito, one 125,000 Cubans who migrated to the United States between April and October of 1980 in the mass exodus called the Mariel Boatlift. Rodríguez’s return to Cuba was for an exhibition of his work that he titled “Nature Boy” after the name of the 68-foot shrimping boat that first took him and 30 family members to the United States.

He has been posting all this week on Roads & Kingdoms’ Instagram account about his return, what he found, and what he and his family had left behind. Here’s an excerpt. Follow throughout the week here.

Due to the U.S. embargo, getting to Havana is a bit complicated. Since I was born in Cuba, I am allowed to travel there on a humanitarian visa, to visit family. Under the permit, I am allowed to bring my wife and daughters. They can travel with their U.S. passports. I, for some reason, need to travel with my U.S. passport and Cuban passport, using the Cuban one to enter and leave the island. All flights from the U.S. are chartered, all leaving from Miami.

The man sitting next to me on the plane left Cuba two years ago and is going back to visit his family for the first time. We had to wait 14 years to see our family after we left. It’s good to see how things have improved for families that are separated. He left Cuba on what he quietly termed “a chain.” It’s a smuggling term, one person leading you to another and then another, until you make it to the Mexico/U.S. border and ask for political asylum. He went on flights from Cuba to Panama, then Haiti, Costa Rica, Guatemala and then finally by bus through Mexico to the Matamoros border crossing, thanks to people assisting him along the way. He was a construction worker in Cuba and had built numerous rafts for kids to leave the island but was too scared of the sea to leave on one himself.

As the plane descends, I put on my headphones and watch a video of my daughter playing the classic Cuban song ‘Guantanamera’ on her piano. The plane lands.

In our luggage, we have 25 original paintings and 40 books. Sending them to Cuba earlier ran into complications because a courier was not given a visa by the U.S. government, so we brought them ourselves. The institution where I was having my exhibit cautioned me that bringing books into Cuba, especially in English, and from the United States, could be problematic. They may be considered ‘ideological’ by the government. A representative from the institution is supposed to meet us at customs to assure their entry. We hope that the pink and purple suitcase and ‘Smurfs’ backpack they are in will help us breeze through.

We go into the airport terminal in Havana and are immediately greeted by officials yelling “VIP, quieres VIP?” Do I want VIP? It takes me a second to figure it out. They are offering VIP treatment: for a fee you can bypass all the lines at the airport. Communism and VIP treatment don’t make sense to me, but it’s only the first of many surprises. The country is doing everything possible to bring in hard currency.

After we get through passport control, our bags are scanned in an x-ray machine, and a guard immediately points them out for inspection. “Open it”, he says. “What are these?” Books, I say. “Why so many? What’s in them?” Words, I say.

Soon, a number of customs officials gather, five or six. They notice some of the books are in a child’s bag and ask, “are these for the kids?” Sometimes, I say. “They must read a lot!” There are 40 books overall. The questions keep coming as I wait for my contact to arrive with all the proper forms from the institution where I am having my exhibit.

There is so much activity, calls for higher ups, books opened and looked at for content. Then I notice the officials looking at some of my silly children’s books and cracking a smile. Soon enough my contact calls out my name and rushes over with all of the official stamped forms, saying I’m allowed to bring the books into Cuba. That they are for exhibition purposes only, that they are to be looked at in a museum setting and not meant to be read. That they are for temporary loan only and not being imported into the country.

Throughout the world, most of my designer friends are worried about the future of books, and whether or not print as a medium matters anymore. Cuba is isolated, the Internet is very limited and mostly unavailable to the public. In 2014, it may be one of the few places on the planet where books are still considered dangerous.

On the way from the airport, we drive by the Interior Ministry at The Plaza de la Revolución, where I remember Fidel Castro giving many of his speeches from when I was a child. I’m told the plaza has lost some of that character since he stepped down. On the side of the building is a giant Che Guevara portrait.

After settling into our apartment in the Vedado section of Havana, we head out for something to eat. There aren’t many places open around our area, so we head to a place that was recommended to us, called VIP Havana. There are those three letters again, VIP, derived from English of all things. In a neighborhood of buildings in rough shape exists this pristine restaurant, 20 foot ceilings, floor to ceiling big screen, pianist playing all night. Full of mostly foreigners and the locals that can afford it. It’s part of a wave of foreign investment, this place is owned and operated by a Spaniard and his Cuban wife. The next day I mention how VIP Havana didn’t seem to jive with the ideals of Communism and I get a feeling that to many locals, Communism is some sort of quaint epoch of the past. It’s confirmed many times later during my trip. What moves people in Havana is money.

I take a ride south from Havana through the countryside and to my hometown, El Gabriel, about an hour by car. When we arrive, neighbors and friends are there to greet us, hugging and kissing my daughters, whom they’ve never met. One of my best friends from childhood, William, pictured here, takes me on a bike ride through town to visit his house and family.

I have stayed in touch with William since I left Cuba when we were both 8 years old and in the same third grade class. We write letters a few times a year and send them via couriers. When my family needs help in town he’s there for them, and when he’s needed help with things that are hard to find in Cuba, I’m there for him. This is very common amongst Cubans from small towns, a sense of community and helping in any way we can.

It’s rare to be able to see how one decision affected one’s life. He sees what his life could have been if he had had the opportunity to leave. I see what my life in town would have been had I stayed and grown up there. We always share stories about all of it. He’s fascinated by how things work in America, things he’s never seen or imagined. I have four other friends like him from the block, his brother Cristobal, Yeyo, Osmel, and Osledys. Osledys finally left the country and is in the U.S. now.

Behind him is his daughter Yennifer, my Goddaughter, who was baptized in my absence years ago. William works as a farmer at a cooperative outside of town, and raises pigs in his backyard, all for sale. He gets by, but it’s very difficult in many ways.

Follow the rest of Edel Rodriguez’s journey on the Roads & Kingdoms instagram.