Skippered Charters are affordable and convenient

Leave the work to us!

Take the pressure off with a Skippered sailing vacation. Whether you're looking to charter for the first time or just leave the work to a trusted professional, a Skippered vacation lets you enjoy as much or as little sailing as you want.

Professional, courteous and discreet, Sunsail Skippers are local experts who know all the best places to moor up, dine out and discover the hidden treasures of your destination.

Leave your generic summer behind and start sailing into an endless horizon of crystal clear waters, flawless blue skies, and verdant island paradises. Relax on the beach, bask in the spectacular scenery, taste the French-Caribbean fusion cuisine and explore the tiny villages scattered along Tortola’s shores.

Summertime sailing means warm weather, reliable conditions, and gentle breezes ready to speed you between enticing island destinations. With locations both nearby and remote to explore, we have summertime sailing destinations to suit both experienced adventurers and sailing newbies alike.

View availability in The BVI

Speak with Team Sunsail: 844-483-6943

Sunsail 444 - 4 Cabin Catamaran #1 Yacht of 2016

Our most popular charter yacht, the Sunsail 444 offers smooth sailing with four en-suite cabins and a wealth of amenities to match.

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Convertible Saloon

This yacht has a convertible saloon that is included as a double berth in the maximum capacity.


This yacht has two forepeaks accessible through the forward cabins. They are not separated from the forward cabins, are very small and are only suitable for a small child or extra storage. They are not recommended as berths for your charter and are not included in the maximum capacity of your yacht.


4 cabins/10 guests (3 cabins/8 guests with Skipper).

 Price Match Guarantee

Charter your vacation with confidence

Sunsail represents the best value and experience in sailing charters. To ensure you agree, should you find a similar vacation as in same size, type and age of yacht in the same destination and dates at a better value, we guarantee to match it. Please speak to a Sunsail Vacation Specialist for full details. 

Choose Sunsail

Stunning sailing destinations 
Flotilla routes
Types of yachts
44 yrs
Creating vacations
4 hr
Service guarantee