The Romeo and Juliet star accompanied British skipper Alex Thomson on an exhilarating 50-mile sailing sprint around the Isle of Wight, as part of the annual sailing regatta, Cowes Week.
With the wind in his hair, the suited sailor and former Burberry model appeared to be relishing the challenge as he raced to secure the £10,000 prize fund for his chosen charity.
But it was not meant to be. Narrowly missing the top spot, Douglas and the crew finished in second place this afternoon. A valiant attempt, though.
Booth is currently starring alongside girl-of-the-moment Hailee Steinfield in Romeo and Juliet, which has been adapted for the screen by creator Julian Fellowes.
The film also stars Homeland icon Damian Lewis and Gossip Girls Ed Westwick.