About Sail Connections

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 his 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 enjoys the sailing paradise of New Zealand's Bay of Islands. During the slow times of Covid, Robert sold Vavoom and has been building solo a new boat from the Elliot stable. 

Robert is on deck to personally guide and advise you on your charter holiday plans. He's 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 

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

Brian Cross, Charter Processing and 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 available to experience. Changes forced by the pandemic has meant Brian also taking up the charter processing role. This involves attending to customer services once charters are confirmed and supporting our charter groups right through the sailing vacation journey. 

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 that's needed. Brian works from his home in Canterbury, NZ, where his equine interests keep him active in his spare time. 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

For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter ...

Latest Blog Posts

  • Look What's Been Happening at Sail Connections

    Look What's Been Happening at Sail Connections

    Rob's Boat Build: a Covid lockdown project where Sail Connections' Robert Cross sets out to build an 11.5m plywood composite sailboat going solo (within reason): a real DIY boatbuilding project if ever there was one

  • Welcome Back to the World of Charter Sailing

    Welcome Back to the World of Charter Sailing

    Covid-19 vaccinations are rolling out, and countries dependent on the tourist dollar are now well-equipped to manage their borders. So while the pandemic is impacting communities still, there's no question that your next sailboat vacation is getting closer every day.

  • Whiting Sailing: NZ's Seachange Experience

    Whiting Sailing: NZ's Seachange Experience

    We are pleased to get behind Whiting Sailing, and their latest sailboating service out of Auckland, home of the America’s Cup. In the Whitings, NZ has a family of sailors who place the joy of sailing and shared experience first and foremost

  • Personal Care on Charter Part II: Evading Insects & Sunburn

    Personal Care on Charter Part II: Evading Insects & Sunburn

    Some more advice on protecting your body while on your sailing holiday charter. using products that are good for the natural environment too. Also explaining our free Charter Pack offer available on every charter sailing holiday booked with Sail Connections.

  • Personal Care on Charter Part I: a Message and a Free Offer

    Personal Care on Charter Part I: a Message and a Free Offer

    Some advice on protecting your body from environmental factors while on your sailing holiday charter. Recommendations that are good for the oceans and the planet too. And a free offer to demonstrate our case, available on every Sail Connections boat charter booked.

The Sail Connections Guarantee

One contact - every option - advice you can trust.

  • Matching any competitive offer
  • Sourcing boats with discounts available
  • Personalising our proposal just for you
  • Qualifying the operator as well as the boat
  • Advising without bias based on 25+ years of experience
  • We do more than just book yachts!

We will match any discount website offer on charter boat price, and still provide our customary high level of service.

Get in Touch

The Essential Guide to Sailing Holiday Charters

The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is jam-packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.

Download Guide

Enquire about a charter...

For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter.