Another option is to join a pre-organised rally, where a fleet of yachts follows the same route in a coordinated manner. Island Cruising NZ, for example, offers three month long rallies which start in New Zealand and head to the Cook Islands.
While you won’t always be sailing side-by-side, you’ll have the opportunity to connect with like-minded sailors who are navigating similar challenges and experiences at the same time. These rally events offer a structured approach that blends the excitement of global (or local) exploration with the security and camaraderie of a supportive community.
The Oyster Owners World Rally
For sailing enthusiasts and adventure seekers, the Oyster Owners World Rally represents the pinnacle of ocean exploration. This exclusive, 16-month circumnavigation is open only to Oyster yacht owners, providing them with the opportunity to sail across three oceans, covering 27,000 nautical miles and stopping at 27 incredible destinations.
The route
The carefully planned route ensures sailors experience the best wind and weather conditions, allowing for smooth and exhilarating passages between some of the world’s most stunning locations. The rally sets sail from Antigua and travels through the Panama Canal, Galapagos Islands, Marquesas Islands, Tahiti, Bora Bora, Tonga, Fiji, Vanuatu, Australia, Indonesia, and Mauritius, among many others, before returning to the Caribbean. Each stopover offers a mix of breathtaking scenery, unique cultural experiences, and exciting local events.
Who can enter?
To participate, you must own an Oyster yacht of at least 45 feet. If you don’t own one yet, Oyster Yachts offers options to build a new yacht or assist in purchasing a brokerage Oyster. All entrants must commit to the entire rally, ensuring a full circumnavigation experience.
Preparation and training
The level of preparation required depends on whether you already own an Oyster, plan to sail yourself, or intend to hire professional crew. For experienced owners, Oyster recommends at least two years of preparation, including participation in their 18-month rally training programme. For those purchasing a brokerage yacht, two to three years is advised to allow time for refits and familiarisation. Building a new Oyster requires even more foresight—typically a three to four-year timeline, factoring in yacht construction, sea trials, and positioning the vessel for the rally start in Antigua.
Support and concierge services
One of the most compelling aspects of the Oyster Owners World Rally is the unparalleled support and camaraderie. A professional, world-class support team is available throughout the journey, providing safety, logistical assistance, and technical expertise. Oyster also offers a Concierge Team, which helps sailors personalise their adventure, whether through guided excursions, exclusive events, or cultural immersion activities. Past highlights have included rum cooking classes in Antigua, canoe racing in Tahiti, and dinghy safaris in Fiji.
A life-changing experience
Sailing in the Oyster World Rally is a transformative journey. Participants describe it as a once-in-a-lifetime experience that challenges and enriches them in ways they never imagined. From witnessing awe-inspiring sunrises over open waters to exploring remote jungles and interacting with diverse cultures, every leg of the journey brings unforgettable moments.
Past and future rallies
Since the first rally in 2013-14, Oyster has successfully organised multiple editions in 2017, 2022, and the ongoing 2024-25 rally. The next editions are scheduled for 2026 and 2028, with anticipation building for yet another extraordinary voyage.
Latest update from the 2024-25 Rally
The current Oyster World Rally fleet recently made landfall in Grenada, marking their return to the Caribbean after crossing the Equator for the second time. They were greeted with Caribbean rum punch and warm hospitality at Port Louis Marina, celebrating their achievement as they near the completion of their circumnavigation.
Ready to set sail?
For those seeking the ultimate sailing adventure, the Oyster Owners World Rally is an unparalleled opportunity. Whether you are an experienced sailor looking for the next great challenge or a new Oyster owner eager to explore the world in style, this rally promises adventure, luxury, and lifelong memories.
The next rally sets sail from Antigua on 18 January 2026—will you be on board?
