In her mid 30s and trying to make sense of her floundering relationship, Regina is restless. Throwing caution into the wind, she books herself a one-way ticket to the Caribbean and joins the crew of a small, vintage racing yacht to satisfy her growing appetite for adventure. Once aboard the old yacht in Antigua, Regina and her fellow crew members work tirelessly under the watchful eye of its cantankerous owner, as they prepare for the passage back to Australia. During a sultry sunset party on a clifftop, Regina encounters an alluring man. When her sailing trip is abruptly cancelled, Regina sets course for Europe aboard another boat, leaving the budding romance in her wake. Released from former ties and without a home, Regina returns to the Caribbean. She moves into a rustic shack and as the only white resident in the tiny community, she must forge a new path. A new life beckons, but are her dreams worth abandoning the comfort and security she has back home? This is a true story of Regina's wanderings in the Caribbean, her passion for sailing and the unexpected, of love lost and found, and her search for freedom.