Work Leading Teens on Adventure Tours in the Caribbean

A Leader Passing the Torch

Article and photos by Andy Schell
Resources updated 10/12/2023

Teens on the tour sitting atop a rocky perch on a remote Caribbean island.

I am on an airplane, flying to the Caribbean island of Saint-Martin / Sint Maarten to captain a sailboat. When I arrive, Lauren from Broadreach picks me up at the airport, and we go on a wild ride around the island to our small base hidden in the mangroves. Chickens and cows block the roads, tropical fruit trees shade the sidewalks, and people of every color wail by on mopeds.

We arrive at Broadreach’s base on the northern end of St. Martin, the French side of the smallest divided island in the world. The staff consists of 40 or so twenty-somethings, split evenly between SCUBA instructors and sailboat captains. Down the rabbit hole, I descend into a solo travelers’ utopia. I mingle with a unique and diverse group of people — a far-ranging mix from around the world: South Africans, Kiwis, Swedes, Brits, Scots, Aussies, and Canadians. The mosquito-bitten nights are long, and the days laboring at the base in the hot sun feel longer. But what an experience it was.

Teens on the tour come from all over the world.

Leading the Tour in St. Martin

I am the leader of an adventure travel operation. On the eve of our first expedition, I am paired with my co-lead Shanon (a SCUBA instructor from Texas), and we are briefed on our 13 students. Our itinerary will see us away from St. Martin, unsupported, for three weeks, stopping at several neighboring islands and sailing, hiking, diving, exploring, culturally interacting, and generally altering our perspectives on life.

The leader and co-leader of the teen tour relaxing on a boat.

We ferry 13 teenagers and their gear out to the anchored boat. We meet 13 wide-eyed, homesick, eager kids. I see myself four years ago when experiencing a new country, a new culture, and a new way of life for the first time. It is time to pass the torch and become a huge part of these kids’ first experiences abroad — experiences which I hope they will take along with them long after our expedition.

Shanon and I instantly become more than just sailing and SCUBA instructors. We become adventure guides, psychologists, doctors, and mentors. The kids will emulate everything we do for the next three weeks, and we will have as much to do with their enjoyment of the trip as the weather, the scenery, or the locals.

I took this responsibility extremely seriously. Drinking on the program was strictly prohibited, and we would have to abstain for the next three weeks. But it didn’t matter, and I didn’t miss it. Instead, we would sit around the cockpit after dinner and share “glums & glows,” our daily ritual of rehashing the day’s activities.

We anchor in a small cove at Ile Fourche, a neighboring island north of French / Swedish St. Barths. Ile Fourche is uninhabited, has no vegetation (thanks to a hundred years of roaming goats), and scoured peaks that remind us of the Galapagos. The ocean relentlessly crashes on the east side of the cliffs along the desolate coast — uninterrupted from Africa.

After dinner, I propose to my group an adventure before dawn, trekking to the tops of the cliffs for the sunrise. I had never been up there, and according to the charts, there was no trail, only rocky outcroppings to scramble up, punctuated by the occasional cactus. The kids agree to go.

Sharing an Adventure with Teens

We take our dinghy ashore under the cover of darkness. The blanket of stars comforts us just as the twilight of dawn casts its first orange glow over the eastern horizon. The way is steep but manageable, and we make it to the summit in time. We each find a comfortable ledge to dangle our feet — a quiet place. We are careful not to get too close to the edge, for it is 1,500 feet straight to the ocean. The only noise we hear is the waves crashing on the shoreline below. Then the sun rises.

But that morning, I was interested in something other than the sunrise. Though I had a camera, there was no urge to take pictures. Though I had my journal, there was no urge to write. Instead, I sat on that rocky perch of the beautiful island and just watched the kids. The orange glow of the dawn gradually illuminated the expressions on their faces. No one spoke that morning; they soaked it all in. I watched and saw myself just four years ago in the faces of each kid on that ledge.

Andy Schell is a professional captain and freelance writer who lives aboard his sailboat Arcturus in Annapolis, MD and travels extensively.