Sunsail Limited – 93 North Park Place Blvd, Clearwater, Florida 33759
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.
"Our hired captain exceeded our expectations. She was professional, knowledgable about sailing & the area. She made excellent recommendations while also listening to our suggestions."
— St Martin, Skippered Charter
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.
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!
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.
From the top to the bottom of the Caribbean, Sunsail has it covered from St.Lucia, Antigua, Grenada, St.Martin and British Virgin Islands.
Discover Italian coastlines; sail from stylish Palma, Croatia and Turkey; explore the Sporades, Cyclades and Ionian in Greece.
Discover a small piece of paradise with turquoise seas and golden sands from our base in Mahe, Seychelles.
Explore the beautiful Whitsundays or the island paradises of Tonga or Tahiti in the Pacific.
Soak up the culture and sunshine in awe-inspiring scenery in the Andaman Sea from Phuket.
Discover panoramic beauty, the diversity and great outdoor adventure of Vancouver Island in North America.
The best value, the biggest choice and the latest yachts and catamarans from 35–53ft.