Back in 2019, the guys I sail with and I chartered a 50′ monohull out of Tortola and spent ten days exploring the Virgin Islands. It was one of those trips you don’t really understand in the moment — but later you realize it stamped itself permanently into your memory.
We hopped from island to island: Jost Van Dyke, St. Thomas, Tortola, St. John… sailed straight into Cinnamon Bay… jumped off the Willie T… drank Callwood Rum in Cane Garden Bay… we all loved exploring these waters and islands. It was pure freedom, pure adventure, and one of the best stretches of days I’ve ever had.
Every morning I’d wake up with the sun, launch the drone from the deck, and fly it over whichever island we were moored off. Sometimes I landed it back on the boat myself, and other times Frank would reach up and catch it by the landing gear as I brought it in. I got good at navigating a drone over open water — even while we were underway — and that gave me views of these islands I’ll never forget.
In a lot of places, you could still see the scars left behind by Hurricane Irma. Huge sailing yachts piled into unnatural heaps, buildings and houses still collapsed — even two years later. It was a reminder of how powerful nature can be, and how much these islands have endured.
But man… what a trip. Ten days of living like Jimmy Buffett and Kenny Chesney, just moving with the wind, the water, and the sun. I’m lucky I got to experience this with the guys — and luckier still that I brought home photos to relive it all.
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