Luxury Sailing Holidays

Enjoy your Oyster luxury sailing yacht charter anywhere in the world. Holiday with our incredible range of Oyster yachts in exotic sailing destinations.

Oyster charter yachts typically reside in the Mediterranean and New England from the middle of June through to the end of September. The boats then spend October and November relocating to their next port, starting the Caribbean winter season on the 1st of December and remaining there until the end of April, fitting in with the usual yachting seasons.

However, an Oyster luxury charter is not limited to these sailing destinations. If you are interested in sailing cruises in areas such as Alaska, Thailand or Australia, please contact us with your inquiry. We will be more than willing to try to accommodate you.


Scotland Sailing Holidays

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Oyster Caribbean Sailing Yacht Charter


Caribbean Sailing Holidays

Offering a lifestyle as exotic as it is laid back, Caribbean sailing charters provide the perfect luxury escape from December through to April. A myriad of beautiful and unexplored islands are sprinkled across this tropical paradise.

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Oyster Mediterranean Sailing Holidays


Mediterranean Sailing holidays

The Mediterranean is a fantastic sailing destination for the experienced skipper and novice alike, looking for the perfect Mediterranean sailing holiday. Its crystal-clear waters, spanning from Croatia in the East to the French and Italian Rivieras in the West, provide exciting challenges and a breathtaking backdrop for a crewed Meditteranean yacht charter.

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Maine, New England

New England

New England Sailing Holidays

An extremely popular vacation spot, New England yacht charters are renowned for excellent sailing conditions, rugged coastlines, picturesque landscapes and charming beach towns. Immerse yourself in nautical culture with a luxury sailing yacht charter around Maine or Newport.

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UK South Coast

UK Sailing Holidays

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2023 Greenland

Greenland Sailing Holidays

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Maine Sailing Holidays

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