The 'Stepping Stones' campaign features a man arriving late to a sailing regatta, watching his team preparing to race without him.
The man, who is wearing Timberland's new Formentor Boat shoes, leaps across the competing yachts to join his crew out at sea.
The ad will run throughout the summer in Italy and Asia and will launch in the UK early next year.
The ad was directed by hip hop music video director Gil Green. Tim Delaney was the creative director, art director and copywriter on the ad. 305 Films, Miami produced the ad, and the media agency was Vizeum.
Tim Delaney, chairman at Leagas Delaney, said: "Timberland has extremely well regarded values within the sailing community. This spot plays to those strengths highlighting the valuable role it can play in the fun to be had while enjoying the great outdoors."
'Stepping Stones' follows on from Timberland's biggest integrated campaign, 'Nature Needs Heroes', which launched at the end of last year.
The ad was the brand's most environmentally-focused campaign so far and promoted its Earthkeepers collection, which is made with materials such as recycled rubber and recycled PET.
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