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 bareboat 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.

Founded in 1990, Sail Connections has built 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. As an enthusiastic and experienced sailor and traveller who takes great joy in sharing knowledge and being part of your charter experience.

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 liase 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.

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

Receive a personalized proposal with boat, cost and extra options as applicable.

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

Latest Blog Posts

  • A Sailing Holiday in Croatia

    A Sailing Holiday in Croatia

    In 2017 Sail Connections' Robert Cross took time out of the office for a two-week sailboat charter in Croatia. Here Robert reports on his sailing holiday adventure aboard a Dufour 350 travelling from Dubrovnik to Split return.

  • Getting the Best from your Charter Sailing Holiday

    Getting the Best from your Charter Sailing Holiday

    Your sailing holiday is a big adventure for all concerned. An investment in time before setting sail will reap rewards on the water. Like any venture, good preparation is key to success in chartering a boat.

  • Charter Boat Technology: Things you Need to Know

    Charter Boat Technology: Things you Need to Know

    Today’s charter boats have all the electrical conveniences of modern living. On board however you are a long way from the grid. Before setting sail, it’s important to understand the limitations of the electrical power source and the tools it drives.

  • Chartering a Sailboat with Crew Supplied

    Chartering a Sailboat with Crew Supplied

    A sailboat charter that includes a paid crew means one of two things: crewed bareboat with your party joined by freelance skipper and sometimes cook; or full-service charter on a boat with permanent, professional crew attached.

  • Bareboat Charter on a Larger Catamaran

    Bareboat Charter on a Larger Catamaran

    There's a charter boat trend towards larger catamarans. Enjoy a bareboat sailing holiday on a big cat such as the Saba 50 or Lagoon 52, their six double cabins providing enough room for two families or a group of friends

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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Receive a personalised proposal with boat suggestions, pricing and optional extras as applicable.