When young Han Solo (Alden Ehrenreich), who describes himself as a driver and a flyer, is offered a job working for a bigtime gangster by Tobias Beckett (Woody Harrelson), his faithful companion Chewbacca (Joonas Suotamo), isn't as thrilled about the prospect. Beckett does, however, offer sage advice: "Assume everyone will betray you and you will never be disappointed."
Four successful women in their sixties — Diane (Diane Keaton), Vivian (Jane Fonda), Sharon (Candice Bergen) and Carol (Mary Steenburgen) — each have something in her life that she needs to set right. Vivian is a wealthy hotel magnate who has been ignoring love for most of her life, settling instead for flings.
Sharon (Candice Bergen), a Supreme Court justice, still hasn’t gotten over her divorce and hates the fact that her ex-husband is dating a woman young enough to be his daughter. Carol (Mary Steenburgen) is married, but her husband shows no interest in her. Diane (Diane Keaton) is a widow whose grown daughters treat her like a child.
Having read the book Wild the month before, but feeling unable to relate to it, Vivian decides to introduce the women to Christian Grey – the handsome title character of the bestselling novel Fifty Shades of Grey. The other women protest her choice at first, but soon each one is captivated by the story. From discovering new romance to rekindling old flames, they inspire each other to make their next chapter the best chapter.
World-traveler Tami Oldham (Shailene Woodley) journeys to the island of Tahiti, where she meets and quickly falls in love with Richard (Sam Claflin), an avid sailor who introduces her to the world of sailing. Over the next five months, their romance blossoms and the two bond over their shared love of adventure and travel.
Richard is approached by friends who request he sail their boat to California in exchange for $10,000 and plane tickets home. Richard agrees, and Tami joins him on the 4,000-mile voyage across the Pacific Ocean. During their travel, they learn of an approaching hurricane and attempt to avoid it, unintentionally sailing directly into the storm as it changes course. Richard tells Tami to go below deck where she is knocked unconscious. When she wakes, the storm is over, the boat is badly damaged, and Richard is nowhere in sight.
Eventually, she discovers Richard floating amongst debris in the ocean, but he is too injured to help her navigate the ship towards land. Alone in the middle of the Pacific with no radio contact and a quickly decreasing food supply, Tami must take control of the wrecked boat and brave the treacherous waters in a desperate attempt to save them both.
Based on the memoir Red Sky in Mourning: A True Story of Love, Loss, and Survival at Sea by Tami Oldham Ashcraft with Susea McGearhart.