At the close of the past two Oyster World Rallies, Richard and Ali Hadida stood on the dock in Antigua’s English Harbour, welcoming home a small armada. After 16 months and 27,000 nautical miles, dozens of Oyster yachts returned from their circumnavigation to cheers and hugs. For the sailors, the homecoming is bittersweet. They will miss the sense of adventure and camaraderie at sea, even as they are elated by the accomplishment. To mark the moment, Richard—a longtime Oyster owner who acquired the U.K. shipyard in 2018—would join his wife to present each crew with a commemorative glass globe. “We’ve felt the incredible excitement and closeness of the groups after everything they’ve experienced,” Richard says. “We were looking at each other and thinking, ‘I want some of that.’ ” In January, the couple cast off themselves. Their 89.5-foot Lush joined 22 other Oyster yachts in Antigua to begin the journey anew. The lead-up included seminars,..