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.

Sail Connections was founded in 1990, with the current management 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. 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 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.

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

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.

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Latest Blog Posts

  • Huahine: Something Special in Tahiti's Society Islands

    Huahine: Something Special in Tahiti's Society Islands

    A sailing holiday charter in Tahiti offers up the idyllic Society Islands, where most charters are sailed from Raiatea return. Other options include a one-way charter from Huahine to maximise downwind sailing. Add a short land-based Huahine stay, and get the very best out of your Society Islands charter.

  • Charter a Gulet: Luxury Cruising in Classical Style

    Charter a Gulet: Luxury Cruising in Classical Style

    For your next sailing holiday, particularly in the eastern Mediterranean but in some other surprising places as well, consider chartering a gulet. Today's gulet is now a modern charter boat built for a unique vacation experience enjoyed in complete passenger comfort and luxury living aboard

  • Charter Sailing Sicily, including the Egadi Islands

    Charter Sailing Sicily, including the Egadi Islands

    On our 2018 Mediterranean charter we made a spot decision to spend time in Sicily. We chose to sail out of Palermo, a convenient base for going east to the Aeolian Islands or west and south the same distance to the Egadi Islands. But the main factor was a near-new Oceanis 38 available just 3 days out from charter

  • A Fleeting Sailboat Tour in Corsica and Sardinia

    A Fleeting Sailboat Tour in Corsica and Sardinia

    After an uneventful passage from Villefranche-sur-Mer to Corsica, a 95 nautical mile passage to the port of Calvi, we had nine days to deliver our boat to its Ajaccio base. Just enough time to explore Corsica’s west coast and visit northern Sardinia, as long as we kept moving

  • A Week of Sailing the French Riviera

    A Week of Sailing the French Riviera

    A sailing charter in the South of France suggests a cruise among the super yachts along the Côte d'Azur, the glitz and glamour of the Riviera. There's more to the French Mediterranean coast; westward lies another charter experience, where the coastline is dotted with seaside towns and quiet bays.

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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