Sailing Charter Destinations Worldwide

Choosing the Best Place to go Charter Boat Sailing

Let us introduce you to all the top-rating sailing destinations the world has to offer: beautiful places where there's a wide choice of modern catamarans, monohull yachts, motor boats and traditional sailing vessels available for your bareboating or crewed boat charter. 

We travel extensively to research and review all the world's popular sailing destinations, inspecting our charter boat fleets to ensure maintenance standards and design suitability. We collect the best local knowledge available on all the places we operate, recommending destinations that meet your budget, interests, level of sailing experience and group needs. We share our accumulated knowledge for you to make your informed choices, before you go sailing on the holiday of a lifetime.   

Sail Connections can place you on a bareboat or crewed charter in just about any sailing destination world-wide.

On the one hand the major sailing hubs offer permanently-located boats with good operators and the perfect packages for destinations that they know intimately: the Greek Islands, Croatia and the whole northern Med., Tahiti, Thailand and the Caribbean hotspots.

On the other hand, there are the smaller companies who excel in their flexibility, alternating between the seasons in different locations. This is particularly the case with the trans-Atlantic shuffle: boats domiciled in the Mediterranean that move to the Caribbean when the seasons change, working the Americas according to booking demand. These are the companies we go to with enquiries for less renowned but equally appealing charter destinations. Places such as the Canary Islands, Aruba, Bonaire, Curacao-San Blas, Bocas del Toro and the Grenadines. 

If you have the time and the budget we can make it happen: in the most iconic sailing locations on the planet, and in places less travelled. 

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

Latest Blog Posts

  • After bareboat chartering in the Gulf of Naples, a client reports back

    After bareboat chartering in the Gulf of Naples, a client reports back

    At Sail Connections we are always pleased to get client debriefs. We are especially delighted to receive positive reports, and here's one we must share. If considering the Gulf Of Naples/Amalfi Coast as a charter destination, this report is well worth a read. 

  • 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.

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.