Skippered Yacht Charter Vacations

Explore some of the most beautiful destinations in the world on your own yacht, at your own pace, with your own private Skipper.

  • Qualified Skipper with local knowledge
  • Skipper takes care of daily running of your yacht
  • Learn from scratch or improve your sailing skills
  • Relax on-board and let your Skipper take control

Check Availability

Skippered Yacht Charter

Take the pressure off with a skippered sailing vacation. Charter a beautiful yacht from our world-class fleet in one of 25 worldwide destinations. Our experienced skippers can leave you free to relax on deck as much or as little as you like.

Skippered sailing charters are perfect for less experienced sailors looking for a relaxing break or for newbies wanting to see some of the world’s best cruising grounds. Even expert sailors can benefit from a skippered yacht charter, getting a chance to relax and enjoy a stress-free holiday.


How does it work?

You can have a Skipper for your entire charter, or just a day or two to help you settle into your yacht or the destination. They’ll use their expert local knowledge and sailing know-how to plan an itinerary based on your interests and how you would like to spend your holiday. Or if you’re happy to go with the flow, they can take the lead, choosing the perfect stopovers to visit, restaurants to eat at, and the best hidden bays and beaches to loll on.

Who are our skippers?

We have a team of friendly, qualified and experienced Skippers available to hire at any of our destinations and we will choose the one best for you based on your requirements. Some of our Skippers have been with us for a long time and customers request them year after year – in fact Gael at our Athens base has been invited to one of his regular customer’s wedding!

How much does it cost?

Our Skippers are hired by the day, and you’ll be charged a daily rate on top of the cost of the boat charter. You’re also responsible for keeping them fed, watered and well rested, so you’ll need to make sure you cover their provisioning and accommodation needs*. They’re an easy-going crowd, so they’ll be happy as long as you’re happy!

*Skippers require use of their own cabin, so bear this in mind when choosing your yacht. Also, you can conveniently add a provisioning package for your skipper - Our Vacation Planners can help you book your skipper and pick the perfect yacht for your group!



Wild, exotic and remote; cosmopolitan and cutting-edge; untouched and tranquil, discover 26 incredible sailing destinations.

Caribbean sailing holidays


From the top to the bottom of the Caribbean, Sunsail has it covered from St.Lucia, Antigua, Grenada, St.Martin and British Virgin Islands.

Mediterranean sailing holidays


Discover Italian coastlines; sail from stylish Palma, Croatia and Turkey; explore the Sporades, Cyclades and Ionian in Greece.

Australian sailing holidays


Discover a small piece of paradise with turquoise seas and golden sands from our base in Mahe, Seychelles.

South Pacific sailing holidays

South Pacific

Explore the beautiful Whitsundays or the island paradises of Tonga or Tahiti in the Pacific.

South East Asia sailing holidays

Southeast Asia

Soak up the culture and sunshine in awe-inspiring scenery in the Andaman Sea from Phuket.

North American sailing holidays

North America

Discover panoramic beauty, the diversity and great outdoor adventure of Vancouver Island in North America.


Our fleet of yachts

The best value, the biggest choice and the latest yachts and catamarans from 35–53ft.



New to Sailing?

Even if you’ve never set foot on board a boat before, you can enjoy a sailing holiday in your choice of 26 incredible locations.


Find out what specials we are offering this week

Find out more

Why should you sail with Sunsail for your vacation?

Find out more

Brochure Request

Our Sunsail Vacations, Schools and Events brochures, will help give you that extra inspiration. Request your copy and start planning your next adventure!

Request a brochure

Sunsail Newsletter

Don’t miss out on all the latest news, deals, giveaways and features direct to your inbox.