Our Sailing Holiday Charter Services

Connecting You with the Best Sailboat Charter Options Available 

With the largest portfolio of charter boats on offer in the 11 to 18 metre range - catamarans, monohull yachts, motor boats and traditionally styled sailing craft. We offer the widest range of choice - with optional extras and local services arranged as required - and we have all the world's best sailing holiday destinations covered.

At Sail Connections we are all about facilitating a quality yet affordable sailing holiday. Whether you want to go bareboating or on a crewed yacht, wherever you want to go charter sailing, we will guide you through the process. So you and your group of family and friends can live the sailboat holiday dream!

The Sail Connections difference: one contact, every option

Sail Connections began in 1990 with the desire to share the rewarding experience of sailing holidays. In the early days our services extended right up to chartering super yachts for ocean voyages and major events. Today Sail Connections has a tighter focus. We want to make the pleasure of sailing a reality for more people like us, to make boats available for self-sail or with crew, and to make the world's sailboat cruising destinations accessible to everyone who loves to sail. 

We use modern tools but stick to the old ways - personal service. We subscribe to not just one but seven boat charter databases on which operators around the world have their listings. We run consecutive searches on each of them and present a selection with our recommendations. That's where Sail Connections stands out. Online searches you see on other websites use a single database.

We will match any competitive offer. But expect us to be surprised if a competitor offers a better price!

Advice you can trust from people who love bareboat sailing holidays

To us the personal approach is what matters. When we discuss your bareboat charter, our commitment is to match our offer exactly with your requirements. We create a holiday package to fit your needs, your sailing capabilities and your budget. And we make sure that before you cast off everything is in place for a successful charter. We discuss your destination options in depth to help you get the holiday experience you are looking for. We discuss the level of sailing experience you will have aboard, and suggest the most suitable destinations and boats to match. We put together your provisioning preferences, on board extras and crew if required. In short all that's needed for that perfect sailboat vacation experience.

In three decades of bareboat and crewed sailing charter experience, we have formed great working relationships with boat owners all over the world. Our partners range from local boutique charter operators to the largest multi-destination companies. As an independent agent we are completely objective in addressing your needs, committed to presenting you with the best-value options available in your chosen destination.

The Sail Connections team's passion for our boat charter business is matched by our practical sailing knowledge and experience. We understand what we must do to make your holiday a success. And we do it. 

Finding your ideal charter boat

We have access to a wide range of premium catamarans, monohull yachts, motor vessels and traditionally-styled gulets for charter. In agreeing to list boats for charter, we travel regularly to meet with suppliers and inspect their boats to ensure they are of a suitably high standard.

We work with you to match you to the right boat, based on:

  • Number of guests and accommodation requirements
  • On-board comfort expectations
  • Crew configuration - bareboat, skipper and/or cook 
  • Personal holiday preferences and objectives
  • Best value for money from several quoted options

Helping you plan the sailing itinerary

Mindful of what you are seeking in a sailing holiday, we work closely with you on your cruising itinerary. It will be one that enables you to visit the best places, taste the yummiest food, meet the nicest people, experience the most enjoyable sailing conditions, and find the right balance between relaxation and entertainment. Together we will put together a plan that:

  • Minimises windward sailing, often using one-way trips
  • Avoids long or rough passages
  • Identifies some top spots, rated on both cultural and natural features
  • Makes it easy to get to some great restaurants and activities
  • Takes account of time frames for passages and stops

Sharing our local knowledge, and giving you peace of mind

Sail Connections can organise your charter sailing vacation anywhere in the world. We are all well-travelled sailors, and love to share our knowledge of exotic places. What we promote is what we know best. In turn our clients are generally quick to pass on their sailing holiday experiences, which helps ensure our knowledge base is constantly being updated.

Using our experiences in sailing the world's best charter regions, we assist you in making your destination decision, setting sail, and getting the most from your bareboat/crewed charter experience.

Our service includes:

  • Advising the best time to charter
  • Connecting you with friendly local operators
  • Informing how best to prepare
  • Getting there
  • What to expect when you arrive
  • Local customs and policies
  • Sailing conditions to expect

When you talk to us about your sailing holiday, we do more than just book your boat charter. We prepare you for the experience and answer all of your questions along the way. We do everything to ensure there are no surprises at the other end.

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

Latest Blog Posts

  • Personal & Environmental Care on Charter: a Message and a Free Offer

    Personal & Environmental Care on Charter: a Message and a Free Offer

    Since my early boating days I’ve lamented over the chemicals put in the ocean. I'd think back to school, when a teacher poured a coloured chemical into water, then challenged us to remove it. That demonstration proved how easy it is to put unwanted additives in water, but how difficult to remove them.

  • The Virgin Islands: Who, What, Where?

    The Virgin Islands: Who, What, Where?

    Putting the Spanish Virgin islands, US Virgin Islands and British Virgin Islands in context for charter sailing. An extensive group of islands all attractive sailboat vacation options when chartering in the Caribbean. In fact very attractive, when considering the choice of beautiful places to visit and the ease of getting there.

  • 10 Ways to a Healthy Mind in a Healthy Body: It Starts with a Sailing Holiday

    10 Ways to a Healthy Mind in a Healthy Body: It Starts with a Sailing Holiday

    At Sail Connections we’re all about the personal approach, and we like to share our sailing adventures, and sometimes our deeper thoughts on chartering, having done it so often ourselves.

  • Five Alternative 2020 Mediterranean Sailing Holiday Destinations

    Five Alternative 2020 Mediterranean Sailing Holiday Destinations

    There’s more to the Mediterranean than the high-profile destinations. In 2020, why not expand your horizons, get a little off the beaten tourist path and discover some understated gems. Here are this year's five best lesser-known Mediterranean sailing holiday destinations, all well worth considering for your next voyage.

  • Benefits of Bareboat Sailing in Flotilla

    Benefits of Bareboat Sailing in Flotilla

    Ever considered a sailing holiday in flotilla? Meeting people through the common bond of sailing is a rewarding experience. It expands horizons and circles while leaving some of the best holiday memories to take home. And strength in numbers can bring peace of mind when sailing unfamiliar waters.

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

Enquire about a charter...

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