Winners of the award «Person of the year» in sailing according to PROyachting were the Olympic bronze medallist Stefania Elfutina and her coach Viktor Ayvazyan.
Lanfranco Cirillo was awarded the «Philanthropist of the Year award» for his support of the Russian Olympic sailing team. Lanfranco Cirillo is an Italian architect who has been working in Russia since the 1990s.
In 2013 Fantastica became world champion in this class.
In the nomination «Discovery of the Year» PROyachting noted the founders of Black Water Sailing Team - Andreas Savvydis, Maxim Merzlikin, Alexander Zaytsev.
In the category «Sailing coverage» the winner was the financial and economic magazine Forbes.
«Sailing Event of the Year» was a large-scale innovative project of All-Russian Sailing Federation National Sailing League aimed at popularization of sailing in the country.
In the category «Children's Coach of the Year» PROyachting noted coach Svetlana Krotova. In 2013, she became «Coach of the Year» as part of another sailing award, «Yachtsman of the Year», established by the Russian Yachting Federation. Svetlana Krotova has been teaching young yachtsmen for over 50 years.
The winner of the «Photo of the Year award» was Ruslan Yakupov. It is the only award where the winner was chosen by subscribers of the PROyachting Instagram and Facebook pages.
Organizers also established a special prize for professional sailing photographer Evgeniya Bakunova in this category.
Her photo taken during the St. Petersburg stage of Extreme Sailing Series was included in the top twenty best sailing shots of 2016 according to the international jury of the contest.
In the mock nomination «Kettle of the Year» was won by Marina Demchenko, editor-in-chief of Fashion Collection magazine, who assembled a team of young Russian designers to participate in the PROyachting CUP 2016 business regatta. Although Marina and her team competed against more experienced sailors, they managed to win «bronze of the competition».
The first place in the Wednesday Night Race won the Alex Team (Irek Tenishev, Alexander Mikhailik, Igor Bragin, Irina Erokhina, Alexei Tarasov). They were awarded with Marine Diver watches by Swiss watch manufacturer Ulysse Nardin.
The winners of Tuesday Warm-Up Race were No Pasaran team(Mikhail Loskov, Nikolay Khlistov, Valentin Uvarkin, Ekaterina Sycheva, Igor Manshin).