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What’s On – Yachting Holidays 2025/26

June 2025 – French Riviera Boutique Cruise

Our luxury 51ft Jeanneau yacht hosted an unforgettable 10-day adventure from Marseilles to Nice. A fantastic trip enjoyed by all – check out the highlights on our Facebook page.

June 2026 – Greek Islands & Beyond

We’re planning something truly special:

  • 10 days based in stunning Corfu before cruising the North Ionian Greek Islands and mainland coast.
  • Sail in style aboard spacious 42 to 46ft catamarans and yachts.
  • Optional add-on: a unique road trip through Albania.

Full details in the event flyer – access it from the Overseas Holidays page.

Boatshows in 2026

In May 2026 we’ll be attending the Turkey Charter Meetup and gulet show in Gocek and Marmaris – the Turkey charter market is in resurgence with some great operators in yachts and gulet holidays and we’ll be there doing the homework.

Then come chat with us about charter and holiday opportunities at:

The Pittwater Sail Expo, October 2026, Royal Prince Alfred Yacht Club.

Sydney International On Water Boatshow– Darling Harbour 12-15 November 2026

October and November are the best times to book for 2027 in the Med or Turkey – with really good deals available

Racing, Regattas & Pittwater Charters

Our First 40 racer/cruiser Leeward has a full calendar of racing and regattas for 2025/26, run in partnership with Allsail.

Highlights of the Season:

  • RMYC Monday & Friday Twilights – defending top division champions 2024/25.
  • Broken Bay Island Series (4 passage races) – defending outright champions 2024/25.
  • Pittwater Regatta – February 2026 (2nd place in 2025).
  • Sydney Harbour Regatta – March 2026 (2nd in 2024).
  • Yachting Holidays is also the major sponsor of this event giving away a 7 day Sunsail charter in Greece or Croatia as the major regatta prize.
  • Sail Port Stephens Race Week – April 2026 (2nd in 2024).
  • Lion Island Series – May 2025 (five Saturday races).

Want to be part of the action? Join the crew for a race, or charter Leeward (bareboat or skippered). Other yachts and catamarans are also available through the Allsail Pittwater fleet.

Boatshows in 2026

In May 2026 we’ll be attending the Turkey Charter Meetup and gulet show in Gocek and Marmaris – the Turkey charter market is in resurgence with some great operators in yachts and gulet holidays and we’ll be there doing the homework.

Then come chat with us about charter and holiday opportunities at:

The Pittwater Sail Expo, October 2026, Royal Prince Alfred Yacht Club.

Sydney International On Water Boatshow– Darling Harbour 12-15 November 2026

October and November are the best times to book for 2027 in the Med or Turkey – with really good deals available

June 2025 – French Riviera Boutique Cruise

Our luxury 51ft Jeanneau yacht hosted an unforgettable 10-day adventure from Marseilles to Nice. A fantastic trip enjoyed by all – check out the highlights on our Facebook page.

June 2026 – Greek Islands & Beyond

We’re planning something truly special:

  • 10 days based in stunning Corfu before cruising the North Ionian Greek Islands and mainland coast.
  • Sail in style aboard spacious 42 to 46ft catamarans and yachts.
  • Optional add-on: a unique road trip through Albania.

Full details in the event flyer – access it from the Overseas Holidays page.

Racing, Regattas & Pittwater Charters

Our First 40 racer/cruiser Leeward has a full calendar of racing and regattas for 2025/26, run in partnership with Allsail.

Highlights of the Season:

  • RMYC Monday & Friday Twilights – defending top division champions 2024/25.
  • Broken Bay Island Series (4 passage races) – defending outright champions 2024/25.
  • Pittwater Regatta – February 2026 (2nd place in 2025).
  • Sydney Harbour Regatta – March 2026 (2nd in 2024).
  • Yachting Holidays is also the major sponsor of this event giving away a 7 day Sunsail charter in Greece or Croatia as the major regatta prize.
  • Sail Port Stephens Race Week – April 2026 (2nd in 2024).
  • Lion Island Series – May 2025 (five Saturday races).

Want to be part of the action? Join the crew for a race, or charter Leeward (bareboat or skippered). Other yachts and catamarans are also available through the Allsail Pittwater fleet.