| Inside Fleet Trophies | 2023 Winner |
| Diamond Seamanship | 1st Zak Cowell
2nd Sienna Faulkner |
| Diamond Trophy | 1st Hannah Child
2nd Harry Daniels 3rd Max Hurst 4th Hugo Langley 5th Olivia Lovegrove |
| Emerald Seamanship | 1st Amy Filtness
2nd Chloe Charlton |
| Emerald Trophy | 1st Freddie Tyler
2nd Angus Cock 3rd Cody Macdiarmid |
| Ruby Seamanship | 1st Max Faulkner
2nd Finn Walsh |
| Ruby Trophy | 1st Lucas Day
2nd Lyra Doyle 3rd Jenny Simpson |
| First Bronze in Ruby | 1st Ben Ketley
2nd Jack Marfleet 3rd Finn Walsh |
| Gold Seamanship | 1st William Marfleet
2nd Elvi Coates |
| Gold Trophy | 1st Oscar Coates
2nd Thomas Child 3rd Charlie Bradshaw |
| Endeavour | Blake Lovegrove |
| Most improved sailor | Max Brand |
| Outside Fleet Trophies | 2023 Winner |
| Slow fleet overall | Sonny & Joel Simpson |
| Feva | 1st Sonny & Joel Simpson
2nd Scarlett MacLennan & Issy Bartlett 3rd Sam Cook & Zac Minnis |
| Topper | 1st Izzy Kelly
2nd Sofia Bellomo 3rd Zac Murrell |
| Fast fleet overall | Alex Canham |
| Laser 4.7 | 1st Morty Mastin
2nd James Blackmore 3rd Jacob Green |
| Laser Radial | 1st Alex Canham
2nd Sam Grout 3rd Muiris Capon Telford |
| Hannah Stodel Endeavour Trophy | 1st Willum Taylor Green
2nd Florrie Golding |
| Good Sportsmanship | Harry Fuller |
| Overall Trophies | 2023 Winner |
| Viking Trophy | Sonny Simpson |
| Tomato Trophy: Most number of 1sts | Lucas Day |
| Most Positive Cadets | Alex Bartlett & Janey Clarke |
| First Tollesbury Sailor | John Clarke |
| Best Dressed Boat | 1st: “Nemo” – Isobel Lovegrove
2nd: “Charlie & the Chocolate Factory” – Eddie Hall 3rd: “Jaws” – Hayden Andrews |
