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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

  • Modern Consumer Tech on Sailing Charter: do we really need it?

    Modern Consumer Tech on Sailing Charter: do we really need it?

    When thinking about a sailing holiday, it’s natural to wonder whether to bring our modern gadgets along for the ride - or leave them behind entirely. Technology is so deeply woven into the fabric of our daily routines. So should we pack our tablets and smartphones or is a sailing charter the perfect opportunity to fully disconnect and reset?

  • Gulet vs. Catamaran: which is the Best Charter Boat for you?

    Gulet vs. Catamaran: which is the Best Charter Boat for you?

    Planning a sailing holiday in the Mediterranean is a dream come true for many, with its crystal-clear waters, historic ports, and sun-soaked islands. Once you’ve chosen your destination, there’s still a crucial decision to make: should you charter a classic Turkish gulet or opt for a modern catamaran? Both offer unique experiences, so let’s dive into a comparison to help you make an informed choice for your group’s holiday.

  • Chartering with a Crew: the Options and all the Advantages

    Chartering with a Crew: the Options and all the Advantages

    A sailboat charter that includes a paid crew can mean different things: a crewed bareboat with your party joined by freelance skipper and sometimes cook; a boat that must have a skipper included, and the full-service charter with permanent, professional crew attached.

  • 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 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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The Essential Guide to Sailing Holiday Charters

The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is 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.