Connecting People Everywhere to the Best Sailing Vacations Anywhere
For three decades the Sail Connections team has been introducing people to the pleasures of bareboating and crewed sailboat charter holidays all around the world. Our mission: to put you aboard the best charter sailboat in the destination of your dreams at the price that fits your
Whether you are an experienced crew of mariners looking for a full bareboat adventure, an occasional sailor leading a group of family or friends on vacation, or a sailing novice with the dream of going places and getting there under sail, we can put you on a boat charter in any one of the world's amazing sailing destinations.
Our service is ruled by personal communications, not algorithms. We talk to you and help you find the right boat in the right place to meet your group objectives in the style that fits your budget. Our services include full bareboat, crewed bareboat and fully crewed scheduled charters. We are also a referral point for sailing professionals conducting occasional sailboat tours who take bookings by the cabin.
Sail Connections was founded in 1990, with the current owners operating the business since 2010. Over that time we have continued to build an international reputation for excellence in charter boat services. We are proud of our record in helping people everywhere experience the joys of sailing on vacation.
Meet our team of charter sailing consultants
Robert Cross, Director: Sales & Administration. Robert has been sailing all his life. Starting out holidaying on the family keelboat in northern New Zealand, in his 20s he worked as skipper for a yacht charter company in the Ionian Islands of Greece. Returning to New Zealand Robert gained blue water sailing experience and enjoyed the thrills of racing a three-crew Elliott 5.9 trailer yacht, later moving up to another Elliot design, the 44 foot pilothouse yacht Vavoom.
Robert purchased Sail Connections in 2010. It's a vocation and a pursuit that lets him share with others his passion for yachting and sailing holidays. When not travelling to explore new waters and research the best charter destinations and operators world-wide, Robert can be found in the sailing paradise of New Zealand's Bay of Islands.
Robert is on deck to personally guide you through the process of organising your charter boat holiday: an enthusiastic and experienced sailor and traveller who takes great joy in sharing knowledge and being part of your charter experience. Contact Robert.
Carolyn Moloney, Sales. Carolyn is originally from Southern California born into a family of boat builders. She grew up around and on the ocean and has a genuine passion for sharing the experience of boating with others. She has done considerable offshore sailing and coastal cruising around the world including the Caribbean, the islands of the South Pacific and the Mediterranean.
Carolyn comes from a technical background in America and Europe and now pursues her passion as part of the Sail Connections sales team. She now calls the Bay of Islands home, returning frequently to Southern California.
When Covid struck and the sailing world all but shut down, Caroline quickly found work in another industry. We stay in touch and Caroline hopes to return to selling sailing holidays in the future.
Brian Cross, Marketing. Brian is responsible for Sail Connections' marketing function, which mainly consists of keeping the website up to date with all the new boats and exciting sailing destinations steadily coming on-stream.
With sailing in the blood and plenty of yachting experience in his younger days, Brian talks the charter business language. He also calls on his many years of experience in organisations large and small to provide policy and strategic support when the need arises. Brian works part-time on a consultancy basis from his home in Canterbury, NZ. Contact Brian.
At Sail Connections, our passion is yachting. Our pledge is to make the right connections for the greatest sailing adventure you can imagine.
Charter Client Reviews & Feedback
What Sail Connections' clients say about us after their charter boat sailing holiday experiences