On the eve of WW1, amidst the turbulence of the Ludlow Massacre and the Triangle Shirt Factory fire, the young Haskell brothers Davey (16) and Jacob (21) dream of escaping the poverty of their lobsterman life in Deer Isle, Maine.

Their sailing talents catch the eye of the powerful New York Yacht Club, with a chance for glory in the prestigious America's Cup race series.

However, the brothers' bond is tested as they both fall for Edith, a captivating Irish maid. Family loyalty is at stake, and now the pursuit of sporting fame threatens to drive them apart. Complicating matters further, someone must stay behind to care for their ailing parents.

When a near-fatal accident leaves one brother hospitalized and consumed by revenge, a compassionate Latina nurse helps him heal, showing him a path beyond bitterness. Meanwhile, the millionaire yachtsmen harbor dark secrets. A glamorous concubine is hidden away on a luxury yacht, leading to blackmail and scandal.

As the bachelor heir to the Vanderbilt railroad fortune grapples with his future, preferring the freedom of the sea over his family's wealth, the Haskell brothers must navigate their own choices between love, family, and ambition.

Can they overcome the trials that threaten to tear them apart, or will the winds of change leave them stranded in the past?