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About Windward Sailing Limited

A yacht charter company run by keen sailors, providing a high quality service which can be tailored to your needs. Windward sailing is based on both sides of the Solent, in Ocean Village, Southampton, Gunwharf Quays, Portsmouth and at Cowes on the Isle of Wight. These bases give access to a wide variety of ports and small harbours, from Chichester in the east to Lymington in the west, all available within a day sail. It is also an ideal starting point for crossing the English Channel via Bembridge Ledge or the Needles. We also participate in events further a field with races across the Atlantic and in the Caribbean.

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Companies and organisations have made use of our expertise to organise corporate events, including participating in major regattas for instance Cowes Week, or specific events such as the Rolex Fastnet Race. We always endeavour to ensure that our clients gain the maximum benefit from their sailing experience. A full catering service is available ranging from providing victuals for your yacht to organising sumptuous seafood buffets


Racing can be either bareboat or with a skipper on a variety of yachts ranging from a Sigma 38 through to a state of the art Volvo 60 round the world race yacht. We have a great wealth of experience both inshore racing and offshore racing through the Royal Ocean Racing Club's including the Fastnet. A rare opportunity is also offered for individual crew members to experience racing on Grand Prix yachts with experienced skippers as far a field as the Caribbean.


We provide and charter a varied fleet of yachts, so with our skill and experience we can tailor your sailing requirements to the right yacht and the correct situation for your needs. You may wish to charter a bareboat or skippered yacht either with your family or with a group of friends either in the Solent area or Caribbean. Alternatively, if you are unable to get a full crew together we can offer other sailing opportunities. As an example, we can organise weekends sailing on one of our yachts, offering crew places to individuals.

Stag and Hen Events

Follow the Royalty to the Isle of Wight for your Stag or Hen weekend getaway. Find out more