And they're off. The 2026-2027 edition of the Oyster World Rally – a fully supported, 16-month circumnavigation of the world – has begun. Cecile Gauert reports from the start line in Antigua, speaking to this year's participating Oyster owners about to embark on the journey of a lifetime.
As he tells the story, the owner of the Oyster 595 Viva, now on its way around the world, went from browsing “beautiful boat” on the internet to a 16-month world circumnavigation in about four years’ time.
A salesman complimented his “discerning taste,” as he tells the story with humour, and Ian Farquharson went from looking at the Oyster 495 to the 565 and 595 in a matter of minutes of conversation. One month later, he ordered the bigger boat. “Then I had the issue of learning how to sell,” he says, but with the builder’s support, he was able to get ready.
He shared his story with a group of other owners similarly committed to complete a circumnavigation that will bring them back to Antigua, where they started in January 2026, in April 2027.
The group sat around a wooden table in the shadow of the Antigua Yacht Club. A strong, sustained breeze blew through the open bar, unoccupied at this early hour. The fleet of Oysters was steps away, split over two docks against the backdrop of the giants that typically line the Antigua Yacht Club marina. The masts of the Maltese Falcon towered over the Oyster pennants clapping in the wind.
Dockside, it was organised and joyous chaos, with packs of supplies being loaded onto the boats, crew in harnesses making final checks on rigging and masts, technical support staff in navy shirts reviewing last-minute issues, all the while documented by the ever-present Oyster Yachts team.
Barbs and laughter revealed the participants’ excitement at their imminent departure during a fast-paced one-hour conversation that broached topics from their level of sailing experience – quite diverse as the team on the Oyster 825 Viva La Vida includes former sailing Olympians, Barry and Susie Parkin – to whales, orcas, pirates (fortunately few to none on the Oyster World Rally route), ghost ships (rusting fishing boats without AIS) shifting priorities (from earthly worries to what matters most at sea, currents, a full moon, wind, food and water, according to Paul Sercanta, doing his second circumnavigation on Mastegot with wife Helena) and even phosphorescence and how to capture it on camera.
Minutes earlier, they were part of a captive audience listening to weather forecaster Simon Rowell tell them what to expect within the first few days of the rally as they headed west-northwest on their first leg. Owners and crew sat quietly (far more attentive than students in a university lecture) in tight rows of chairs in front of the walls displaying the Antigua Classic Yacht Regatta (ACYR) Trophy winners. A few of them had taken part in the Antigua Classic.
“Everyone who does the rally has to do a qualifying passage. So, most people have crossed the Atlantic. Ours was a new boat in ’24. We needed to break it in a bit. We did the Arc class, the Antigua regatta, and returned to Majorca,” explains Andy Heppel, owner of the Oyster 595 Carina, sailing with his wife Cat and two crew.
Rowell, in a white polo and shorts, is a good-natured and imposing man, a former engineer on oil rigs and experienced sailor with a degree in meteorology who advises the UK sailing team. He provided lots of information in the session, peppering his talk about the Inter-Tropical Convergence Zone (ITCZ), boundary layers, currents and trade winds with words such as “tropical Armageddon,” “the chaos of boundary" and “awfully big adventure,” which might have given green sailors pause. Not this crowd. They have waited and prepared for this for months.
The rally is a huge commitment of time and effort, but for most, if not all, it is the reason they bought an Oyster sailboat. The massive organisation and support behind the Oyster World Rally, including professional forecasting, is what gives them the confidence to undertake a circumnavigation. “It’s nice to know there are 22 other boats out there,” says Richard Hadida, owner of Oyster Yachts, and first-time participant in the rally. He’s embarked on this adventure with his family, which includes the youngest participant this year (two-and-a-half-year-old Harry), and an experienced crew.
He pondered when to take the plunge but figured the present was as good a time as any. “Why wait?” When they return to Antigua in spring 2027, toddler Harry will have spent nearly half of his life on a sailboat. “The world may be a very different place,” Hadida remarks. That sailboat is the Oyster 885 Lush, which has proven her might with 20 transatlantic crossings and one circumnavigation.
Fresh out of the yard for a full workup, she set out across the Atlantic to reach Antigua with a fresh coat of paint, which includes a recognisable pink whale logo and some atypical additions, such as child-proofing gates and pink yoga mats fitted to the companionway. The Lush team is documenting its voyage on social media platforms as @sailing.lush.
They are part of a 23-strong flotilla of Oysters that signed up for the 2026-27 edition of the world rally. The Oyster World Rally this year counts eight different nationalities, six on Viva La Vida, owned by four friends and neighbours in a small city in New York. They bought the boat used, “the previous owner worked out the kinks,” they say. They are one of the boats with the most experienced crew and with such varied backgrounds, “there will be drama,” they joke. On the appointed day, they were the first to leave the dock. The rally is not a race, but it’s clear some are keen on leading the pack.
The World Rally is a unique proposition among luxury yacht builders. The British boatbuilder started this tradition on its 40th anniversary, launching from Antigua in January 2013.
“One big misconception is we go as a flotilla, but we don’t travel as a pack,” says Heppel. They are points of rendezvous along the way. They were together on the starting line off the island of Antigua, starting at the sound of a cannon (small but mighty and loud) fired from Port Charlotte. Landside, there was dancing and music, filling the yacht club docks with a festive ambience. They will rendezvous in Panama in March to cross the canal, but they will follow their own route. Maps of the former events show a web of tracks that occasionally intersect and wind up and down along a general line.
But if anything happens along the way, they can count on each other. It’s a community of like-minded people, unified by a desire for adventure and a passion for sailing. A WhatsApp query for a missing part quickly gets answered, or radioed, or transmitted with any means of communication available at sea. All the boats are equipped with Starlink. And last year, one of the boats, Raven, rescued a lone rower, which will join the boat along the route this time around.
One goal of this Oyster World Rally is to leave the places they visit better than when they came, if they can. As part of their commitment to regenerative tourism, Oyster Yachts is working with Sarah Darwin, great-great-granddaughter of Charles Darwin, to help reintroduce species displaced by development and human encroachment.
There will be plenty of opportunities for this. Over the course of the 27,000-nautical-mile journey, the fleet will visit places such as the Galapagos, Marquesas, Vanuatu, Australia, Mauritius, South Africa and points along the South and Central American continent.
You can follow the Oyster World Rally on their website and on social media platforms @oysteryachts.
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