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Follow your Yachting Holiday Dream

Yachting Holidays on Sale Worldwide

Best Charters at the Best Prices Available Now! 

These specials cannot be combined with other discounts. Conditions may apply. 


Sail Away on the Charter Boat that's Right for You

At Sail Connections we are specialists in bareboating and fully crewed yacht charter vacations. Our team members have many years' international sailing experience and we are uniquely qualified to advise on every aspect of sailboat chartering. Take a look at our extensive charter boat portfolio, our catalogue of amazing places to go sailing, and the long list of testimonials provided by our satisfied clients. Then talk to us about setting sail in the very best of the world's charter boat holiday destinations.


  • 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 30+ years' experience
  • Doing more for you than just booking your boat!

We match any discount website offer on charter boat price, always with our customary quality service.

Planning your sailing holiday with Sail Connections saves you time and money while giving you total peace of mind. We help you create a sailing holiday itinerary that fits all your needs, including your budget. We have the largest portfolio of quality catamarans, yachts, traditional sailing vessels and motor cruisers available to choose from. Year after year satisfied clients from around the world return to charter their next bareboat or crewed sailboat vacation with us. Prepare to be amazed at the destinations on offer, places we are familiar with as well-travelled sailors ourselves. 

All at no extra charge to you! 

Trending Sailing Holiday Destinations

Top sailing holiday locations where people are looking right now for their next boat charter.

Our Latest Blog Posts

  • 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 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.

  • The value of after-charter destination and boat reviews

    The value of after-charter destination and boat reviews

    At Sail Connections we offer a personal service based on long experience in the business and close attention to what's happening in the destinations we offer. We have also sailed a large number of those places, and can often speak from personal experience.  But we can't be everywhere.

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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