A photographer’s personal travel diary from Cuba

A Southbay photographer travels to Cuba for the first time—her mother and young daughter in tow—and discovers both heritage and healing.

Written & photographed by Lauren Pressey


Cuba has always been somewhat of a mystery to me. My mother was born there—though she and my grandparents fled in 1959, leaving everything they owned and everything they knew behind after Fidel Castro took power. That fact, along with a handful of stories that my grandmother retold countless times before she passed in 2015, was all I really knew about Cuba.

When travel restrictions were lifted recently for Americans, my mother decided to revisit her childhood home. Soon, perhaps, I would discover what Cuba meant to me.

We touched down on the island with a rather intense degree of skepticism. Understandably, my mother had a lingering fear that Cuba wouldn’t let her go home, and I questioned whether it was a good idea to bring my 7-year-old daughter along on a trip that was sure to dig up the most emotion my mom and I had ever experienced. My idea of family bonding, I guess.

Following my grandmother’s passing, this felt like the ideal opportunity to explore Cuba. But upon our arrival, her presence and persistent head-shaking were hard to deflect. She never would have approved of our adventure, but we did it anyway … because, after all, we are her strong-willed daughter and granddaughter.

We arrived on a rainy day (perhaps a sign of good luck or just another day during hurricane season, I suppose) and were greeted by our well-dressed driver, Raul. He eagerly escorted us through the crowds, and we waited as he drove the car around to get us.

I secretly hoped a classic convertible in bright red might pull up so we could explore the island in style, but I quickly realized my expectations and reality were wider than the waters between Cuba and the U.S. Instead we jumped into our provided chariot: a small, black sedan with deeply tinted windows and a few missing seat belts.

My mother has always been a no-nonsense, type A personality, but never before had I seen her so determined. For the next three days we combed the streets of a place she hadn’t been in 57 years—since she was 6 years old. With her keen visual memory, though still fighting off tears, she was able to track down both her home and her grandparent’s estate.

Raul did a little investigating himself and was able to locate her old private school. Photos of Che Guevara and Fidel Castro littered the walls, and the building looked as though not much thought had gone into its care for decades. All eyes were on us as we were let in for a few brief moments and then quickly escorted out. Not exactly the warm reception I was hoping for.

I couldn’t help but feel that the streets of Miramar, the neighborhood of my mother’s school and first home, bore a striking resemblance to Park Avenue in New York City, with large medians flanked by beautiful homes and large trees. Now deteriorated, you could still picture what it might have been like in the ‘40s and ‘50s, during its glory days.

Though it certainly was still filled with life, I couldn’t get past the feeling my grandmother must have had when she was forced to leave it behind. Whether you believe the government was good or bad at the time of the revolution, the lives of many Cubans were torn apart as a result and the country they were proud to call home was changed forever.

Our next destination was that of my great-grandparents’ estate, Finca Maita. My mother’s memory of the home was of its modern ‘50s style and the impeccable grounds it sat upon. Orange groves lined one side, where my mother recalls receiving her first and only bee sting, and a welcoming porch spanned the front where the family gathered to enjoy the weekend and play dominos.


Without hesitation, my mother pointed it out as we drove past. Three women sat on the porch—the eldest may have been just shy of my grandmother’s age, along with what appeared to be her daughter and granddaughter. A fitting scenario, considering the circumstances. We introduced ourselves and politely asked if we could take a tour. The granddaughter happily agreed, while the old lady remained on the porch.

So there we stood, in a complete time warp. A framed tapestry that belonged to my family still hung in the entryway. My great-grandparents’ dining room furniture, with beautifully hand-carved hutches, sat just as before. The orange groves, however, were long gone. New paint had been added all around, and what remained of the landscaping was overgrown and unkempt. A portion of the land had also been sectioned off to make room for additional neighborhood housing.

We spoke to the old lady and mentioned how incredible it was to see the same furniture after all of these years, and she quickly denied that it wasn’t hers. Her defensiveness was understandable, but disappointing nonetheless.

Upon our departure, it occurred to me that even after all of this time, she might feel threatened that the original owners might be seeking to claim what belonged to them. Or was it possible that one of her family members fought in the revolution, and she was given the house as a token of gratitude for their contribution? Perhaps she only felt ill will toward us and our American ideals. I couldn’t be sure.

I began to feel utter and complete frustration. So often I had heard stories of the amazing people and culture in Cuba and how I needed to see it before there was a Starbucks on every corner. As a photographer, I’d seen countless photos of historic buildings with classic cars driving past and smiling faces in the streets. My experience thus far warranted anything but a smile. All I felt was sadness for what once was.

Even more so, I felt my grandmother’s heartache for all that could have been. I told my mother we needed to look deeper. We needed to visit the areas that I had seen in magazines and, by God, I needed to take a photo of at least one classic car!

Raul dropped us off at a popular tourist destination in Old Havana, and we walked amongst the old architecture. In that moment, I couldn’t help but feel guilty. Instead of photographing the obvious attractions, I put my camera away and walked along the cobbled streets with my mom and daughter, still seeking our trip’s purpose.

But then came our greatest discovery. The next morning and the day before our departure, we set out early to the town where my grandmother was born and raised: Melena del Sur. Without a single contact to aid us in our search, we held on to the hope that we might find somebody, anybody, whom we could call family.

We drove up and down the streets, stopping locals who graciously did all they could to help us. It didn’t take long before a woman suggested we visit a house down the street. We took her suggestion. We were greeted by my mother’s second cousin and welcomed with open arms.

We spent the day meeting more and more family, talking over Cuban coffee and sorting through countless photos of my mother as a young girl, as well as photos that had been passed down of me and my brothers growing up. My daughter’s eyes lit up at the sight of it all. We were even able to visit the tomb of my great-grandmother, where more emotions flowed as my mother was able to put the pieces of the puzzle back together.

Suddenly Cuba felt familiar, like a cousin itself, and I had finally found the meaning I had been in search of: to reunite with the people that give our lives purpose and that help tell our story. Regardless of politics, these were the people and lives that shaped my mother and, in turn, both my daughter and myself.

We were not there to decide who in Cuba’s history was right or wrong. We were not there to give Castro our money either (as some of our Cuban relatives residing in the U.S. might see it). Ultimately, we were there to find what we were certain belonged to us: my mother’s memories, my grandparents’ pride and our family.