We chose to rent a 41-foot monohull from the Tortola sailing charter, Horizon Yacht Charters. We also made the wise move of hiring a Captain, “Boss,” a 51-year old grandfather of 4 who grew up on Tortola sailing boats and ferries for a living when he wasn’t tending to his goats and sheep. Boss exuded an heir of confidence and calm aboard Island Karma, even during 27-knot winds in the open sea, when the rain and swells left us soaked. We would spend the week sailing to Jost Von Dyke, Virgin Gorda, and Anegada, which was worth the long sail over. We savored the chance to dine barefoot on lobster and conch fritters and making our way to both beaches on the island, Cow Wreck and the equally enticing Loblolly, stopping to see a large flock of flamingoes in the distance. We ended with stops at Cooper Island and Peter Island, before one last Dark and Stormy on Norman Island. A memorable trip that we’re happy to recreate for ActiveTravels clients upon request.