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 front-line team of charter sailing consultants

Robert Cross, Director
Robert Cross

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 calls the sailing paradise of Bay of Islands home.

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.

Sue Assad
Sue Assad

Sue has extensive first-hand knowledge of the boat charter business, having crewed on luxury yachts of varying sizes in the Bahamas, Grenadines and elsewhere in the Caribbean, as well as Tahiti and Fiji the South Pacific. Sue's further sailing adventures include the Cape to Rio race and a voyage from the Canary Islands to Greece.

Sue is in charge of administration and sales support. As such she will prepare all your booking documentation and liaise with you on arrangements. Sue is your go-to person for any queries as you prepare for your charter. 

Originally from South Africa, Sue and her family now call New Zealand home. Contact Sue.

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

  • The Sun Loft 47 Monocat: a Game Changer for Yacht Chartering

    The Sun Loft 47 Monocat: a Game Changer for Yacht Chartering

    A peak season cabin-share sailing holiday with skipper in glorious Croatia in August. Chartering a 2020-model 47 foot sailboat for just 175€ per person per day! This is the reality aboard the Sun Loft Monocat 47: a whole new concept in group charter with friends or extended family.

  • Bareboat Luxury at an Affordable Price: Crunching the Numbers

    Bareboat Luxury at an Affordable Price: Crunching the Numbers

    In 2019 the Bali 5.4 catamaran entered charter fleets with the bareboat option added. Until now such a large boat was only available with paid skipper and crew. This is a significant development in yacht chartering: it continues a recent trend towards larger boats progressively coming into charter on a self-skipper basis.

  • Whale Watching on Charter in New Caledonia

    Whale Watching on Charter in New Caledonia

    Winter is the season for spotting humpback whales in New Caledonia’s southern lagoon. The calves are starting to learn the ways of the ocean while still safely under mother’s watchful eye. The lagoon offers the perfect location for observation, whale watching a highlight of any New Caledonia boat charter

  • Going Charter Sailing? Why you should use a Broker

    Going Charter Sailing? Why you should use a Broker

    Bareboat and crewed boat sailing holidays are growing in popularity the world over. Every year new destinations open up and more of the latest designs in catamarans, monohull yachts, powered and motorsailer craft come into service for charter. With this growth come more ways to arrange your charter sailing holiday.

  • Sailing in the Marquesas Islands: the Ultimate Escape

    Sailing in the Marquesas Islands: the Ultimate Escape

    The Marquesas Islands group is the sort of place dreams of a tropical island escape are made for. Dreams are one thing, but getting there and experiencing these remote and unspoiled volcanic islands is another. The Marquesas lie some three hours’ flying north from Tahiti.

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.