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Sailing Holiday Photos of the Year 2023 - Vote now

Published on: 23 November 2023

03 - Rafting Up (David Novak)

Vote for your favourite Sailing Holiday photo of the 2023 season.

This season, there’s been hundreds of boats on the water, months of glorious sunshine, miles and miles of sailing, thousands of happy customers, and millions of photos to document it all – but it all boils down to this: the Top 12 entries to the ‘Sailing Holiday Photo of the Year’ have finally been announced.

The charter experts have shared their shortlist of their best sailing holiday photos, which include unbelievable sunsets, epic photos from drones, and action shots of people enjoying themselves on a boat. It’s now down to a public vote to see which one will win the crown - along with €1,250 off a 2024 sailing holiday with anywhere in the Mediterranean or Caribbean.

Anyone can vote for their favourite photo - head to to view the 12 entries and choose your favourite!

The voting period runs until Monday 27 November, and the winner will be announced early in December.

Tommy Tognarelli, co-founder of, said: “We love seeing what our customers get up to, and it’s an honour and a privilege to be able to share the best sailing holiday photos of the season from our wonderful customers. Some of these photos are simply stunning.

“We’ve had thousands of happy customers in 2023, and there were so many amazing sailing holiday photos to choose from – it has been a real challenge for our judges to even narrow it down to this shortlist of the top twelve photos, and they really are worth a look.

“If you follow us @PlainSailing on social, then you’ll have seen loads of other ‘Happy Customer Photos’, plus some have featured on our homepage through the season, but we’re excited to see which photo from our Top 12 gets the most votes and wins the grand prize.”