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, boat checks by engineers, and social gatherings, embodying what Ali calls the rally’s “work-hard, play-hard” ethos. The island’s governor fired a cannon to send the fleet on its way. Leading the pack at the outset was Viva la Vida, an 82.6-foot Oyster helmed by former Olympic sailors Barry and Susie Parkin, who co-own the boat with three other couples. “I said, ‘Look, we’re going to race for the first 30 minutes,” Barry says. “We did that quite well, because we won the start—and the race to the first mark.”

The Parkins are members of an eight-nation owner group that includes retirees, active business owners, and composers, as well as several of their children. The boats range from owner-operated Oyster 495s to superyacht-size 885s supported by crew. For those new to the rally, the thrill lies in “going to places very few people have ever been,” says Barry, calling out the Tuamotu Archipelago in particular. “We’ll visit coral atolls with a few dozen inhabitants who haven’t seen a ship for months.”

The Hadidas felt that magic early on. After cruising north to the British Virgin Islands, they sailed 1,000 nautical miles to Panama’s remote San Blas Islands. “They blew me away,” Richard says. His friend, the late Eddie Jordan of Formula 1 fame, once called them the most “beautiful islands on the planet.” On one islet, roughly the size of four tennis courts, locals treated the crew to red snapper, lobster, and piña coladas served in hollowed-out pineapples. These simple, unscripted encounters have become the rally’s touchstones.

From the Caribbean, the fleet crossed the Panama Canal and headed west to the Galápagos, then on to French Polynesia, Fiji, Vanuatu, Australia’s Whitsunday Islands, and Indonesia. Next comes the Indian Ocean, with stops in Mauritius and Réunion, before rounding South Africa and crossing the Atlantic back to Antigua in April 2027. “Equatorial sailing,” Richard calls it. “T-shirts 24 hours a day.”

Yet it’s not always fair skies. During the previous rally, Pau Serracanta and Helena de Felipe Sempere rode out intense storms in the Indian Ocean aboard their Oyster 595, Mastegot. They originally joined the tour because they valued Oyster’s technical support, but have since logged 28,000 miles of solo cruising. “Once you have done the rally, you realize… you can go anywhere,” Serracanta says. “You feel comfortable to go wherever you want to go.”

Even when hundreds of miles apart, the fleet stays in touch via Starlink and social media. Some owners will dip in and out, flying home between legs, but the Hadidas plan to stay on Lush for the full 16 months. “When they give me my glass globe,” Ali says, “I want to feel like I’ve really earned it.”

Top: In January, a fleet of 23 Oyster yachts took off from Antigua to start the brand’s namesake 27,000-nautical-mile rally exclusive to Oyster owners.