About Sail Connections

Connecting People Everywhere to the Best Sailing Vacations Anywhere

For more than 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.

At Sail Connections, our passion is yachting. Our pledge is to make the right connections for the greatest sailing adventure you can imagine.

Meet our team of charter sailing consultants


Robert Cross, Director and Sales. 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 advise you on your sailing holiday plans. He's an enthusiastic and experienced sailor and traveller who takes great joy in sharing his boat and destination knowledge so you can get the very best charter experience. Contact Robert.

Sue Assad, Sales Processing. Sue has responsibility for the very important customer service operations, personally assisting charterers with all their sailing holiday arrangements. Sue expertly provides the vital link between charterer and charter operator from signing up to casting off and beyond.

Sue is an experienced sailor and has worked on yacht crews around the world. She hails from South Africa, and after a period living in New Zealand with her family is now back in her home country. Her working hours are therefore ideal for supporting our European and American clients and providers. Contact Sue.

Brian Cross

Brian Cross, Marketing and Administration. Brian is responsible for Sail Connections' marketing function - which primarily means keeping the website up to date with relevant information on sailing destinations worldwide, the boats available to charter there, and all the things that go to make for a successful sailing holiday venture. 

With sailing in the blood and plenty of yachting experience in his younger days, Brian talks the charter business language. He also calls on many years' experience in organisations large and small to provide system and strategic support and keep the backroom routines ticking. Brian works from home in Canterbury, NZ, where these days it's mainly his equine interests that keep him active in his spare time. Contact Brian.

What Sail Connections' clients say about us after their charter boat sailing holiday experiences

Great communication, good organisation. All went very smoothly. Incredible holiday, sailing amongst the islands surrounding Koh Samui, all organised by the team from Sail Connections. I highly recommend them! Nicholas, Australia, 2023

Fantastic job Sue and Robert! Lou, New Zealand, 2023

Very good service, friendly helpful staff. Tim, New Zealand, 2023

We were very satisfied with the entire experience and would definitely return. The Tahiti Yacht Charter experience was well run . They were helpful ,courteous and very informative during the briefing. Ian, USA, 2022

Your service was in line with the rest of the holiday. Trouble free, professional and a pleasure to deal with. Dean, Australia, 2020

Sail Connections' service was really great! We felt guided through the process, of which we knew nothing about before. Joyce, USA, 2019

Your service was excellent and everything was terrific. Thanks for all your help in insuring a memorable vacation. Dave, USA, 2018

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

Latest Blog Posts

  • Sailing charter versus resort stay: comparing the costs

    Sailing charter versus resort stay: comparing the costs

    A sailing holiday frequently combines with a land-based resort stay. How many nights aboard charter boat and how many nights onshore, or foregoing one or the other due to cost, is often a discussion point. So we did an exercise on the price comparisons between boat and resort. The cost benefits of a sailing holiday are clear

  • Charter catamarans for modest sailing holiday budgets

    Charter catamarans for modest sailing holiday budgets

    Here we highlight some smaller catamarans finding favour with our charterers in the Mediterranean and elsewhere. Robert is our expert evaluator when it comes to helping you select the right boat for your sailing charter, and the following is his personal take on recent introductions to the charter boat market.

  • The popular Bali Catamaran in all its variations

    The popular Bali Catamaran in all its variations

    The Bali catamaran, designed and built specifically with chartering in mind, has become so popular that it’s been hard to keep up with all the new models, hard to spot which one has just the right size and amenities to perfectly fit your group's sailing holiday charter needs. We can help you there.

  • The value of after-charter destination and boat reviews

    The value of after-charter destination and boat reviews

    At Sail Connections we offer a personal service based on long experience in the business and close attention to what's happening in the destinations we offer. We have also sailed a large number of those places, and can often speak from personal experience.  But we can't be everywhere.

  • Chartering in Turkiye: feedback we just have to share

    Chartering in Turkiye: feedback we just have to share

    Turkey is one of those charter destinations that doesn't fail to pleasantly surprise. We're always delighted when we receive such good reports as we did recently from a New Zealand client.

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

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