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.
In the evening, the family gathers around for fresh crab, and Abby spends her time on the phone arranging her work schedule, despite her father’s wishes that she put the phone away. She opens up to Jess that she has no time for dating and has even forgotten how to flirt.
On Sunday morning, Abby hits the ground running, literally, taking a beach jog. She is joined by Trace for a brief moment before he leaves her in the dust. Finally, the two are able to catch up about their current life, including the fact Trace moved back to Chesapeake Shores six years ago to recharge his batteries. He moved into the beach shack, the house that he and Abby dreamed of living in when they were teenagers in love. Abby’s father sold the house to him.
Abby confronts her father about selling the beach shack to Trace and he says that Trace had the money and the dream to fix the place up. She decides to surprise Trace with a visit to the shack. She opens up to Trace about her failed marriage to her ex-husband, Wes, and her life as a single mom.
After Abby leaves the shack, she heads home for dinner, where tensions arise as Abby’s daughters discover that their favorite nanny has quit. Nell and Mick are witnesses when the little girls reveal they know more than they should about Abby and Wes’s custody agreement with their daughters. Mick offers up some of his own parental advice to Abby and she doesn’t react so kindly. Their argument brings up some harsh memories of Abby’s own mother, who ran off to the big city leaving three daughters and son with workaholic Mick to raise. Abby points out just how dysfunctional their family really is, especially when it comes to all the siblings who are currently estranged from Mick.
The next morning Abby heads back to the beach shack to see Trace. She tells him she missed her flight back to New York City but he knows there is something more than that. She confesses that her life has been a lie. Despite having the high-powered job and daughters who are attending the best schools and get the best grades, she is still not happy. She admits to Trace that she was a coward when she left him all those years ago without saying goodbye. Their conversation is interrupted by Jaqueline, an attractive woman who Trace has agreed to go paddle boarding with. Abby takes it as her cue to leave. When she heads home, she is shocked to see an ambulance at the house taking Nell away.
Meanwhile, at the hospital, Mick receives an update that Nell passed out due to low blood sugar. Both Abby and Jess are happy to hear she will be fine, but Abby agrees she should probably stay at Chesapeake Shores until her gran makes a full recovery.
That evening she calls Wes to talk about their girls. She asks why they are under the impression that they will be moving in with Wes and his girlfriend, Gabrielle. He assures Abby that it is about moving the girls to Brooklyn and saving money on private schools. She hangs up on Wes when Trace pulls up on his motorcycle to check in on Nell’s condition. When Abby brings up Jaqueline, Trace assures her the two are not dating but he does enjoy seeing Abby jealous. After seeing how upset Abby is when talking about her conversation with Wes, Trace takes her to their favorite beach.
While at the beach, Trace admits he went to New York to try to win Abby back. When Trace found out Abby was engaged, he turned around and went back home. After that he moved to Nashville to pursue his singing career. He tells Abby that Nashville left him unfulfilled and that is why he returned to his hometown. The mood is lightened when Trace invites Abby to join him for a swim. She takes the plunge and the two share a kiss in the water. After Trace drops her off at home, she goes through a box of all the cards and love letters from her teenage relationship with Trace.
The next morning, Jess and Abby’s sister Bree arrives at the house from Chicago. She is met with coldness from Mick. The sisters all bond over their lousy relationships with men and how it is all related to their father. Bree tells Abby and Jess that she is planning on staying in Chesapeake Shores until Nell has made a complete recovery. Their conversation turns juicy when the sisters want to know all the details about Abby’s night with Trace, including their kiss.
The next morning in the O’Brien house, Carrie and Caitlyn are in the kitchen making breakfast. The girls tell Abby it was grandma who taught them how. Abby heads out to Baltimore to host a very important business meeting at her work branch. Back at the house, Mick and Nell have a frank conversation about Nell’s health. She points out that Mick should focus less on Nell’s health and more on making amends with his three daughters. He doesn’t think a rift exists, but Nell points out that Mick was always a workaholic throughout their entire lives and he should now build a future and legacy with his children.
Back in Baltimore, Abby is shocked when she receives a job relocation offer after her meeting. She mulls over the conversation in her head as she heads back to Chesapeake Shores.
Jess visits her bed & breakfast to find Mick working on just a handful of the repairs that need to be done. Mick tells Jess he wants to patch up his relationship with her and make up for lost time. Bonding over all the bed & breakfast repairs is a good start.
Abby returns to her and Trace’s favorite beach spot, where Trace finds her taking a dip in the water. He asks when she is heading back to New York and she tells Trace about her Baltimore job offer. Abby wants to revisit their kiss and before they have a moment to address it, Fourth of July fireworks set off over their heads. Once Abby realizes the time, she heads to the city center to join her family for the fireworks show. She tells her father about her job offer and he thinks it’s a great idea to move back to Chesapeake Shores. The moment is interrupted when a taxi pulls up and Mick’s ex-wife and Abby’s mother Megan, walks out. Mick confesses that he called Megan, and when asked why, he says, “Sometimes you have to go back and make peace before you can go forward.” Megan’s presence is met with hugs from her granddaughters and daughters. The ultimate surprise comes when the O’Brien’s deployed son, Kevin also pulls up in a taxi.