About Us

Russell and Cherie Waddy are the principals of Yachting Holidays. They have been sailing the Med and other destinations for over 25 years - and organising flotilla and charter holidays for well over a thousand happy repeat customers.

Our Yachting Story

Russell had a long corporate management and sales career in transport, aviation and service companies and had been an avid sailor for years. He joined Allsail Sailing club in the mid 1990s as a member, eventually becoming an instructor and skipper.

Russell and his wife Cherie went on their first Allsail overseas sailing flotilla holiday to Greece in 2001.

Both were hooked and have been organising and hosting overseas yachting holidays, regattas and gulet adventures ever since.

In 2008 they bought Allsail, expanding its Pittwater sailing club and charter fleet – but continuing every year organising overseas flotillas, private charters and regattas in the Mediterranean, Thailand, the Pacific – as well as in the Caribbean and Canada.

In 2019 they bought their own private Beneteau 43ft yacht Pankina which they keep in Greece and sail on her in the northern summer each year.

With the sale of Allsail in 2022 Russell and Cherie created Yachting Holidays to provide a boutique service offering overseas charters, flotillas and regattas  – as well as racing their Allsail Pittwater based First 40 Leeward in major series and regattas in Australia.

They use their expertise, worldwide contacts and experience to ensure their personal clients get the best holidays or charters.

Contact us below or call Russell on +61 419 602327 for a chat about your dream holiday.