Eleuthera is a 110-mile-long island in the Bahamas known as the “isle of freedom,” derived from the Greek word eleutheros, which means free. Upper School Learning Specialist Alicia Brady traveled to the remote island with friends in 2014. Because the island is so small, “I really got to know the people.”

Fast forward eight years: Brady is interviewing with Head of School Henry Smyth for a position at Gilman. Smyth is soon heading to Eleuthera to visit his son, Pitman ’24, who is studying there at The Island School for a semester. Enthusiastic conversation ensues. Later, after Brady learns she is hired, she meets with Smyth again to discuss taking Gilman students to the Island School as one of many global trips offered.

The Island School was founded in 1999 for students from around the world to enjoy semester-long immersion experiences in marine ecology, sustainability, and leadership. Since the early 2000s, a number of Gilman students have taken advantage of the opportunity — either to complete a semester or get a taste of the experience during a shorter visit. Trips were paused during the pandemic; Brady re-introduced Gilman to the Island School this academic year.

In February of 2026, Brady and two other chaperones escorted a group of 10 Upper School students for a weeklong journey on Eleuthera. Some aspects of The Island School felt familiar to the boys. Athletics were clearly a high priority as students engaged in physical training activities from 6–8 a.m. each morning before breakfast. Gilman boys are used to turning in their cell phones at the start of the school day; at The Island School, they didn’t have access to their phones for the entirety of the six-day experience. One participant, Derek Silverman ’28, said it was challenging at first to adapt. “However, that did not last long as all of the semester students were extremely welcoming.”

Other aspects of Island School life, of course, were quite different. As active members of the community, students participated in daily chores and sustainability practices. Their studies weren’t contained to any classroom or building. They worked with scientists from nearby Cape Eleuthera Institute to learn about tides and astronomy. They sat in on conservation talks about the preservation of conch, a large, edible sea snail found in tropical waters. They went scuba diving and snorkeling, and dissected Lionfish, an invasive species, back at the school.

Perhaps the most exciting excursion took them off the island and onto a boat with the researchers. The group captured three nurse sharks, which are slow-moving, bottom-dwelling sharks found in the shallow coastal waters off the Atlantic and Eastern Pacific. Boys helped tag the wild sea life and perform an ultrasound on one that was believed to be pregnant. “The boys were in awe,” Brady said. “It was amazing to watch.”

Silverman called the time he spent interacting with the sharks on the boat his “favorite experience.” But he said the most memorable moments “were those spent in the cabins with my fellow Gilman brothers. I believe that the bonding experiences we had were the most important part of the trip. I cannot recommend it enough.”

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View photos from the shark experience