Abby O’Brien is a force to be reckoned with. The New York City single-mom knows how to jog a treadmill, get her daughters, Caitlyn and Carrie ready for the day, take care of business calls and run a Wall Street meeting, all before 10am! After her meeting she receives a call from her very excited sister Jess, begging her to come home for the weekend and Abby reluctantly agrees.
Abby makes her escape to her hometown, Chesapeake Shores, Maryland where Jess and her grandmother, Nell, are excited to greet her. Jess gives Abby a rundown of what the rest of the family is up to. After dinner, Jess shows Abby her new house, which she is turning into a bed and breakfast, and Abby immediately has questions about Jess’s latest investment. Jess mentions she is already behind in loan payments.
The next morning, Abby and Jess head down to the local bank to take care of a loan for the bed & breakfast. On their way, Abby comes face-to-face with the past in the form of her ex-flame, Trace Riley. Some words are exchanged between the two, when Trace reminds Abby she abandoned him and both their dreams when she moved to the big city all those years ago.
Later on, Jess grabs a bite at the local diner, where she is surprised with a visit by her father, Mick, who fills her in on life in Chesapeake Shores, including his plans to renovate the local church.