The Essental Yacht Charter Guide
The Essental Yacht Charter Guide: What to Know Before You Go

Charter Sailing Holiday Tips

  • The Ultimate Way to Experience America’s Cup 2027: on an Italian Sailing Holiday

    The Ultimate Way to Experience America’s Cup 2027: on an Italian Sailing Holiday

    Discover the best way to experience the America’s Cup 2027 in Naples. Combine world-class racing with sailing Capri, Amalfi & beyond, with expert personal advice from Sail Connections.

  • A Sailing Charter vs a Resort Stay: Comparing the Costs

    A Sailing Charter vs a Resort Stay: Comparing the Costs

    Mixing vacation nights between resort stay and yacht charter is a frequent discussion point among our travellers. So we decided to do an exercise on the cost implications of both options. To us at Sail Connections, the benefits of a sailing charter speak for themselves.

  • Making the Most of a Remarkable Sailing Destination: The Society Islands

    Making the Most of a Remarkable Sailing Destination: The Society Islands

    What truly defines a great sailing holiday experience is how well the charter is planned and structured around what you want from your time on the water.Nowhere is this more evident than in the Society Islands of French Polynesia, a sailing holiday destination we at Sail Connections know so well.

  • Why Our North American Clients Trust Sail Connections

    Why Our North American Clients Trust Sail Connections

    NZ-based yacht charter experts trusted by sailors from USA and Canada. 30+ years’ experience, global reach, and personalised service to North America.

  • Gulet vs Catamaran: Which Charter Boat Is Right for You?

    Gulet vs Catamaran: Which Charter Boat Is Right for You?

    Compare gulets and crewed catamarans in the Mediterranean. Find the right yacht for your group, comfort level, and sailing style.

  • Our Guarantee: More Than Just Price Matching

    Our Guarantee: More Than Just Price Matching

    <p>A message from our Director Robert Cross:</p> <p>At Sail Connections we are proud of our record as a brand that has continuously traded for 45 years. Maintaining an enduring business means staying true to what we do and delivering the very best sailing holiday experience, building loyalty through trustworthiness.</p>

  • Sailing Between US VI, British VI and Spanish VI

    Sailing Between US VI, British VI and Spanish VI

    Step-by-step guide to current regulations for sailing between the British Virgin Islands and US Virgin Islands, and the US Virgin Islands and Spanish Virgin Islands.

  • Why a Lot of Itinerary Advice Misses the Mark for Sailing Holidays

    Why a Lot of Itinerary Advice Misses the Mark for Sailing Holidays

    Learn why many bareboat sailing itineraries found online can be misleading, and how first-hand advice makes all the difference.

  • 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?

  • 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.

  • 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 popular Bali Catamaran in all its variations

    The popular Bali Catamaran in all its variations

    The Bali catamaran, designed and built specifically with chartering in mind, has become so popular that it’s been hard to keep up with all the new models, hard to spot which one has just the right size and amenities to perfectly fit your group's sailing holiday charter needs. We can help you there.

  • Barcelona gets ready for the America’s Cup

    Barcelona gets ready for the America’s Cup

    As well as the competition for the Auld Mug itself, the 37th America’s Cup in Barcelona will incorporate the first ever Women’s and Youth America’s Cup regattas. Chartering Barcelona 2024 will be in demand!

  • Charter Sailing in Greece: It’s not just about the Islands

    Charter Sailing in Greece: It’s not just about the Islands

    Charter sailing tourism started in Greece. It’s still the place where first-time charterers want to go sailing, the place seasoned sailors return to year after year. And there’s plenty of Greece to go around

The Sail Connections Guarantee

One contact - every option - advice you can trust - at no extra cost.


  • Matching any competitive offer like for like
  • Sourcing boats with discounts available
  • Personalising our proposal just for you
  • Qualifying the operator as well as the boat
  • Advising without bias based on over 30 years' experience

We will match any like-for-like discount website offer on charter boat price, while maintaining 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.

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