I am 17 years old as I make this trip across a mere 90 miles of the Atlantic Ocean. My grandparents were the same age when they made the same trip in the opposite direction, having said good-bye to parents they thought they would never see again.

When my grandparents speak of the United States, the conversation is infused with gratitude, and even admiration. But when the conversation turns to Cuba, the emotions seem more raw, more conflicted. There is love, longing, and a fierce pride.

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The legacy of the Cuban Revolution, like all tragic stories, is complicated. So are my feelings about accompanying my father on this historic trip. My grandparents are cautious, wary even—but supportive. And that's no small thing. I cannot imagine what my grandfather must be feeling; he was one of the last men captured on a doomed fight on the beaches of the Bay of Pigs, and one of the last ones freed several years later.

The separation of the United States and Cuba in 1959 as the Revolution turned communist was like a violent, terrible divorce, and the surviving children of both places have been indelibly marked by the experience. There are hundreds of thousands of stories of terrible sadness on this side of the ocean.

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Having dedicated most of his life in public service to the issue of Cuba, my father has become convinced that opening up relations and trade is the most compelling hope we have for the ushering in of a more democratic future of Cuba and its people.

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My father and I notice a genuine pride among the Cubans we come across. It is not a nationalism, so much as a dignity about who they are as a people. You can hear the pride in their voices as they describe the beauty of the countryside, the beaches, the music. There is a lot of smiling in Cuba, despite the heat, despite the scarcity, despite the lack of freedoms, despite the dulled backdrop of ruined buildings.

My father and I felt very welcomed everywhere we went. We went for a walk near our hotel around La Habana Vieja with Mario, the son of a friend of my father’s back in Miami. In Miami, I hear that the city is a lot like Havana. In Havana, I feel that the city is a lot like Miami. Physically, I know they couldn’t be more dissimilar. The 1950s American Chevys and Buicks drive by the grey dilapidated once-grand buildings like astonishing dots of hope. The bright colors and the sheer improbability of these cars in this setting make me smile. And that’s when it hits me. It’s the people—the playfulness of the Cubans—that feels so similar to the exuberance of Cubans back home in Miami.

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More than anything else, I was encouraged by the kindness with which we were met everywhere we went. On Thursday afternoon, our cab driver took us to Pepe’s, a little out-of-the-way restaurant (aren’t those always the best kind?). The owners, Jose “Pepe” and Dolores, sat down and joined us for our meal. I was thinking how right at home I felt. Most of the family ate dinner with us.

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Their son, Alvaro, who was there with his girlfriend Nati, was only five years older than me. He had recently graduated from college, having spent his first two years at Boston University and then transferring to American University to complete his degree. We chatted about the merits of taking the SAT over the ACT, and the drudgery of the application process. I was having the kind of conversation I would expect to have back home, but never in Cuba.

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Issues of life and death, freedom and oppression, opportunity versus scarcity abound. They swirl up and down the winding alleyways of a deteriorated city, while Alvaro’s parents carve out a life for themselves and a future for their children. Nonetheless, there are glimpses of a future capitalistic economy everywhere, right here at Pepe’s restaurant, back in the car with Guillermo’s private car service to shuttle people around. There’s a determination clinging to the pieces of this city seemingly frozen in time. I sensed a cautious optimism. Surely there is a long road ahead to righting past wrongs and extending basic rights and opportunities to those on the island. But as Alvaro and I continued chatting about the dreaded Common App essay—the bane of every college-bound American kid—I realized that there may be a lot more common ground than I thought.

There are a lot of us young adults—Cubans, Cuban-Americans, Americans—who are just starting out our lives, going through the same life experiences. And suddenly, the idea of Cuba starts to feel more like it’s only a mere 90 miles away instead of the entirety of my family’s lifetime away. And the raising of the American flag in Havana is not the celebration of something achieved so much as it is the hope of something just getting started.

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Gabriela Garcia-Ugalde, 17, is a rising senior at New World School of the Arts High School in Miami. She is the daughter of former U.S. Congressman Joe Garcia and the granddaughter of Cuban exiles who fled the island in the 1960s.