A Family of 26 Sailing the British Virgin Islands
June 11, 2016
Herding a Family of 26
Family trips usually mean mom, dad, maybe a couple siblings. This one was different. This was the whole family — brothers, sisters, cousins, aunts, uncles, grandparents, godparents — all 26 of us.
It was 2016, and the destination was the British Virgin Islands. The challenge started long before the turquoise water and palm trees: getting everyone into St. Thomas on the same day, around the same time. Flights had to align because the ferry to Tortola wasn’t waiting for stragglers. Somehow, with a lot of coordination (and a little luck), we all made it through customs and onto the ferry that carried us to the start of our adventure.
Vessels and Villas
Once on Tortola, everyone was assigned a place to stay. Some of us would spend the week at sea, others in villas along the shoreline.
Our family, along with another, was assigned to a sailing catamaran — a massive yacht that was as beautiful as it was comfortable. Between us, it was me and my two boys, plus their family of five, and the boat fit us all with ease. It had four spacious cabins with king-sized beds, two forward crew berths (those little cubby bunks you climb into from the bow), two heads, a full galley kitchen, and wide decks that wrapped all the way around. It was luxurious, steady under sail, and came with both a captain and a mate who quickly became part of the family.
Another branch of the family was assigned to a larger wooden yacht — a boat with double decks, rich wood interiors, and enough charm to make you feel like you’d stepped into a classic Caribbean film.
Not everyone wanted to be on the water, so some stayed in villas. The names alone sounded like postcards: Mood Indigo, a private waterfront villa near Trellis Bay, and Red Rock Villa, perched on the hills of Virgin Gorda with sweeping views over the Sir Francis Drake Channel. These villas became the perfect balance for those who preferred to sleep on land but still be part of the adventure.
Setting Sail
From Tortola, our little fleet took off. Each night had a destination, each stop planned so that our boats could pick up moorings in calm bays. The waters shimmered a clear turquoise blue, and every sail between islands felt like part of the adventure. Whales and dolphins would leap alongside us, racing the waves and swimming in our wake. One day, a massive sea turtle, easily the size of a small car, trailed behind us as if it wanted to join the journey. The captains always knew the route, but for us the real excitement was in what awaited at each stop.
Trellis Bay, Beef Island – Our first taste of island life. Artsy, colorful, and alive with local energy. We wandered through boutiques, browsed Aragorn’s Studio for handmade crafts, and watched vendors pull up by dinghy to our moored boats to sell jewelry, carvings, and artwork right off the side.
Marina Cay – Back in 2016, it was the legendary Pusser’s Marina Cay. Rum punches with umbrellas, seafood on the dock, and laughter that echoed across the water. You could feel the atmosphere of paradise all around, skies bright blue with sunshine, turquoise waters warm and clear, and soft white sand stretching along the shore. A couple of local musicians would play nearby, strumming guitars and singing reggae and island tunes that carried on the breeze. We would sit outside, drinks in hand, watching the kids swim while the music mixed with the sound of the sea. It was a real and unforgettable vibe.
Virgin Gorda – The Baths – Giant boulders stacked like nature’s playground. We swam from the mooring field to shore and spent the day climbing through caves, splashing in hidden pools, and finally relaxing on the white sand of Devil’s Bay. This was also where we grabbed snorkels and followed and floated and swam above schools of tropical fish, the kind you usually only see in saltwater tanks such as yellow tangs, clownfish, angelfish, and damselfish weaving through the coral in a living rainbow..
Cooper Island – A calm anchorage with a beach club that served fresh conch fritters, seared tuna, and crab curry. The rum bar was stocked with more labels than we could count, but the favorites were always the fruity Caribbean cocktails served in tall glasses with little umbrellas.
Salt Island – A quieter stop, known for the RMS Rhone shipwreck just offshore. While some of us snorkeled, others stayed on deck, soaking in the sun and the stillness.
Island Flavors and Marketplaces on the Sea
Meals were part of the magic. Some nights we feasted on soft-shell crabs or grilled lobster, eaten under the stars with the sound of the water lapping against the hull. Other times, we ordered from island restaurants, tasting jerk chicken, crab curry, or orange rum cake before heading back to the boats.
I remember at some of the stops our mate would take the dinghy to shore, and we would follow to wander through the local markets. It was a neat experience, seeing the foods laid out on tables, hearing the voices of vendors, and watching how they worked together in that rhythm unique to island life.
We never had to cook for ourselves. Every meal was prepared for us, with our diets taken into consideration so that everyone had what they needed. Meals were served in the dining area on the boat, where we gathered together as a family, enjoying food that was made with care and attention.
One time we were having hamburgers, because my son loved them, and out of nowhere a seagull swooped down and snatched the burger right out of his hands. We laughed so hard that the whole dining area was shaking with laughter. Moments like that made the meals as memorable as the places themselves.
Why This Trip Stood Out
It wasn’t just about the places we went. It was the feeling of watching 26 people, spread across generations and branches of our family tree, move together through the islands as if every stop had been waiting for us. Each day flowed into the next with ease, from sailing to snorkeling to dining under the stars.
We shopped in local markets, shared meals that reflected both the islands and our own tastes, and laughed until our sides hurt. We toasted rum drinks topped with umbrellas, swam above schools of bright tropical fish, and listened to music that carried across the water.
This was more than a vacation. It felt like a living tapestry, woven from the sea and the land, the boats and the villas, and the people who filled them. The British Virgin Islands gave us the backdrop, but it was the togetherness of our family, every detail falling into place, every moment building on the last, that made it unforgettable.
Written By: Shelley Iverson