Skippered Charters are more affordable and convenient than you think

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.

Sail aboard the acclaimed Sunsail 444 Catamaran in the British Virgin Islands this winter, and you'll get the convenience of a FREE Sunsail Skipper for seven days. Simply book by September 30 and depart between October 1, 2016 - March 31, 2017.

Speak with a Vacation Planner at 844-483-6943 and mention the code SKIPR to get started.

Free Skipper Special in The BVI on the Sunsail 444*

The British Virgin Islands

The Caribbean yacht charter capital

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.

Free Skipper Special Details:

  • Applicable to departures on the Sunsail 444 in The BVI
  • Applicable departures from October - March 2017*
  • Minimum 7-day charters booked by September 30, 2016

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. Launch the virtual tour

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).

Free Skipper Special Details:

  • Applicable to departures on the Sunsail 444 in The BVI
  • Applicable departures from October - March 2017*
  • Minimum 7-day charters booked by September 30, 2016


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.

*Free Skipper Terms & Conditions

  • Only available for charters onboard the Sunsail 444 Catamaran in the British Virgin Islands
  • Provisioning for your Skipper is not included as part of the free promotion
  • Provisioning for your Skipper is required
  • Offer is only available for bookings between August 2 - September 30, 2016.
  • Offer is valid on bookings held and confirmed between the dates above. A confirmed booking must have a deposit on it
  • Offer is for new bookings only. The discount amount must be applied at time of booking, when paying the deposit amount, and cannot be added retroactively
  • The offer is a discount off the yacht charter amount, cannot be applied to any other item/product unless specified above, and is not exchangeable for anything else
  • The offer excludes selected departures - find out more details here.
  • Offer applies to bareboat only
  • Offer is not combinable with any other offer
  • Offer is valid on destinations, products and yachts specified departing between October 1 through March 31, 2017
  • Offer is valid for departures with a boat charter duration of a minimum of 7 days
  • Offer is subject to availability and change and can be withdrawn at any time
  • Offer is not applicable to customers chartering boats for sailing school or regatta/racing events

Choose Sunsail

Stunning Sailing Destinations 
Flotilla routes
Types of yachts
44 yrs
Creating vacations
4 hr
Service guarantee