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What’s On – Yachting Holidays 2026/27

June 2026 – Luxury Hotel and Cruising Holiday out of Corfu

A great time was had by our crews and the brand new Sunsail Leopard 42 catamaran that was part of our fleet was really inpressive as we cruised the Ionian islands and Greece mainland coast – check out the highlights on our Facebook page.

Boatshows in 2026

In May 2026 we attended the Turkey Charter Meetup and gulet show in Gocek and Marmaris – we found the Turkey charter market to be in resurgence with some great operators in yachts and gulets. We’re now better ready to tailor Turkey charters and gulet holidays for our clients.

Come chat with us about charter and holiday opportunities at:

Sail Expo 2026 Australias largest Sail Only boatshow – 17/18 October 2026, Royal Prince Alfred Yacht Club. See the Event

Timber Boating Festival – 7/8 November 2026, Royal Motor Yacht Club Newport. See the Event

October and November are the best times to book for 2027 in the Med or Turkey – with really good deals available. Or talk to us about our Luxury Hotel and Tall Ship Sailing Holiday out of Malta late April 2027.

22nd April to 1st May 2027 – Luxury Hotel and Tall Ship Cruising Holiday out of Malta

We’re planning something truly special:

  • Start with three nights in a top boutique hotel in Valetta old town on the Mediterranean island of Malta.
  • Then transfer to our luxury 115 metre sailing Tall Ship – Star Flyer.
  • We’ll cruise to Syracuse in Sicily – then to the Greek Peloponnese peninsula visiting Pilos, Monemvasia and Nafplio on the way to our destination 7 days later on Saturday at Athens.

From Athens you’re well positioned at the start of the European Spring and Summer.

Full details in the event flyer

Racing, Regattas & Pittwater Charters

Our First 40 racer/cruiser Leeward has a full calendar of racing and regattas for 2026/27, run in partnership with Allsail.

Highlights of the Season:

  • RMYC Monday & Friday Twilights – Top division champions 2024/25, second in 2025/26.
  • Broken Bay Island Series (3 passage races) – outright champions 2024/25.
  • Pittwater Regatta – February 2027 (2nd place in 2025).
  • Sydney Harbour Regatta – March 2027 (2nd in 2024, 3rd in 2026).
  • Yachting Holidays is also the major sponsor of this event giving away a 7 day Sunsail charter in Greece as the major regatta prize in 2026 – in 2027 the major prize is a 7 day Mediterranean cruise for two on a Star Clipper group tall ship.
  • Sail Port Stephens Race Week – April 2027 (2nd in 2024).
  • Lion Island Series – May 2027 (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 attended the Turkey Charter Meetup and gulet show in Gocek and Marmaris – we found the Turkey charter market to be in resurgence with some great operators in yachts and gulets. We’re now better ready to tailor Turkey charters and gulet holidays for our clients.

Come chat with us about charter and holiday opportunities at:

Sail Expo 2026 Australias largest Sail Only boatshow – 17/18 October 2026, Royal Prince Alfred Yacht Club. See the Event

Timber Boating Festival – 7/8 November 2026, Royal Motor Yacht Club Newport. See the Event

October and November are the best times to book for 2027 in the Med or Turkey – with really good deals available. Or talk to us about our Luxury Hotel and Tall Ship Sailing Holiday out of Malta late April 2027.

June 2026 – Luxury Hotel and Cruising Holiday out of Corfu

A great time was had by our crews and the brand new Sunsail Leopard 42 catamaran that was part of our fleet was really inpressive as we cruised the Ionian islands and Greece mainland coast – check out the highlights on our Facebook page.

22nd April to 1st May 2027 – Luxury Hotel and Tall Ship Cruising Holiday out of Malta

We’re planning something truly special:

  • Start with three nights in a top boutique hotel in Valetta old town on the Mediterranean island of Malta.
  • Then transfer to our luxury 115 metre sailing Tall Ship – Star Flyer.
  • We’ll cruise to Syracuse in Sicily – then to the Greek Peloponnese peninsula visiting Pilos, Monemvasia and Nafplio on the way to our destination 7 days later on Saturday at Athens.

From Athens you’re well positioned at the start of the European Spring and Summer.

Full details in the event flyer

Racing, Regattas & Pittwater Charters

Our First 40 racer/cruiser Leeward has a full calendar of racing and regattas for 2026/27, run in partnership with Allsail.

Highlights of the Season:

  • RMYC Monday & Friday Twilights – Top division champions 2024/25, second in 2025/26.
  • Broken Bay Island Series (3 passage races) – outright champions 2024/25.
  • Pittwater Regatta – February 2027 (2nd place in 2025).
  • Sydney Harbour Regatta – March 2027 (2nd in 2024, 3rd in 2026).
  • Yachting Holidays is also the major sponsor of this event giving away a 7 day Sunsail charter in Greece as the major regatta prize in 2026 – in 2027 the major prize is a 7 day Mediterranean cruise for two on a Star Clipper group tall ship.
  • Sail Port Stephens Race Week – April 2027 (2nd in 2024).
  • Lion Island Series – May 2027 (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.