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Andrew Montgomery is the black sheep of the Montgomery family. Seventeen years ago, Andy and his best friend, Kurt, took off for the army and planned to never look back. Once overseas, they realized the depths of their mistake. But once Kurt died in combat, Andy decided to turn his back on his past for good. Years later, Andrew is bound to the US again with an injury. A phone call a few weeks before Christmas changes everything and beckons him home. His father has been involved in a horrible car accident. When Andrew returns to the island, he finds himself in the center of so many ghosts.

Audrey gives birth at the end of February. Although she’s young, healthy, one of the most vibrant people on the Vineyard, the birth is a troubling one—and the baby’s health is cast into doubt. This adds even more stress to an already stressful situation. After all: Christine planned to help Audrey raise her baby, to allow her to return to school and get the degree she so desperately wants. As Christine, Audrey, Lola, and Zach wade the waters of this delicate new family plan, and grapple with the fears surrounding a very sick baby, they find new strength together.

Since Jason drowned over a year and a half ago, Charlotte has struggled moving forward. She owns a popular wedding planning and events business and throws some of the most expensive and intricately coordinated weddings, occasionally featuring celebrities, and always with her fourteen-year-old daughter’s help. But her devastation is so complete that sometimes she struggles to get out of bed in the morning. As Thanksgiving approaches, a celebrity asks Charlotte to plan a gorgeous multi-million-dollar wedding on Martha’s Vineyard.

Kelli Montgomery spent the previous twenty years in a loveless and abusive marriage. Last Christmas, after her brother, Andy, arrived home after decades away, she finally found the strength to leave her husband—but as anyone who’s ever been through such trauma knows, what happens next—the healing process, the rebirth which is the hardest, and most grueling part of healing. Years ago, Kelli and her ex took over her parents’ prosperous real estate business. Now that Mike has officially left the island, the work has fallen on Kelli’s shoulders.

Susan Sheridan left her life in Newark almost a year ago. Since then, Susan, Christine, Lola, Audrey, and Amanda have lived out every life milestone under the sun—from divorce to new loves, illnesses, to second-chance romances, and beyond. Now, after a year of cancer and healing, it’s time for Susan Sheridan to have her happily-ever-after with her high school sweetheart, Scott. There is so much to be done before the huge event—but Susan Sheridan is good at staying busy.

If there’s anything Susan Sheridan understands, it’s that things don’t always go as planned. From her divorce, to her move from Newark, to her cancer diagnosis, finally to Scott popping the question at the Sunrise Cove Inn’s New Year’s Party in front of all her closest family and friends. She never thought she’d find her way back to a love like this. Amanda prepares herself for the ride of her life as she plans a dream-wedding to Chris, a man she’s loved desperately for years. But there’s something off about him. Something that rears its ugly head as the January wedding date rolls near.

When her Great-Aunt Jessabelle passes away and leaves her home to Samantha, Sam and her daughters, Darcy and Rachelle, begin refurbishment on The Jessabelle House, a glorious house not far from the town of Siasconset on Nantucket. Once there, Samantha discovers her aunt's diaries, which reveal dramatic secrets from the past—and still more reasons not to trust the Colemans.

Estelle Coleman is on cloud nine. She's just released a new novel, A Bright Christmas, a joint love letter to her husband, Roland, and her mother, who died so long ago. She's thrilled to reveal another piece of her soul to her incredible fans. This is the life of her wildest dreams. But another romance writer named Margorie Tomlinson can't stand Estelle's fame. She'll stop at nothing to take Estelle down. Margorie accuses Estelle of plagiarism and seeks immediate legal action. Estelle's publisher drops their newest deal, and Estelle's readers begin to turn on her.

Meghan Coleman has been head-over-heels for her husband, Hugo, for twenty-seven years. But one afternoon a few weeks before Thanksgiving, she discovers a box of letters from his ex-fiance, which illustrate a smoldering love, one he never mentioned. Not long after that, she learns her children already knew about the ex-fiance and kept it a secret. Tormented, she finds her world crumbling around her. Who can she trust?

Oriana Coleman is one of the most sought-after art dealers on the east coast, renowned in New York, London, Paris, and Tokyo. She fought tooth and nail to get to the top—and didn't always play by the rules. At the beginning of Oriana's career, her best friend and coworker swapped out a multi-million-dollar painting for a very convincing forgery. When she confessed to the crime, Oriana knew better than to tell anyone she hadn't noticed the painting was a fake. It would have destroyed her reputation and dropped her back on square one.

Hilary and Aria have never needed anyone but each other. Because Aria's father left Nantucket before she was born, Hilary isn't sure why anyone would fall in love on purpose, and she's fought hard to become a sought-after interior designer for Sotheby's. Plus, now that Aria left Tufts University, she's been tagging along with her mother as an interior design apprentice, which thrills them both.

At seventeen, Charlie Coleman was on top of the world. He was captain of the football team, dating the smart and beautiful Shawna David, and on his way to becoming another pillar of his Nantucket community, just like his father before him. But all that changed in the blink of an eye. It's been thirty years since the accident, and Charlie is still overwhelmed with guilt. Why has he been blessed with so much—a gorgeous wife, three children, and two grandchildren, while Nora is left with nothing? Why did he escape that night with his life?

Charlotte Hamner lost her beloved husband Jason three years ago. His death nearly destroyed her—but with the help of her dearest sisters and cousins in the Montgomery and Sheridan clans, she was able to find hope once more, and ultimately build her wedding planning business back to new heights. And against all odds, she found love again with the dashing photographer, Everett.

After a blizzard roared across the island in February, Lola Sheridan was forced to postpone her wedding to Tommy Gasbarro, the handsome Italian sailor who stole her heart two summers back. Their June wedding approaches—and the Sheridan women have a surprise party up their sleeves, one that will shock all involved and make Lola question her allegiances.

Quentin's at the top of his game. He's the nightly news anchor for the biggest broadcast company in the United States. On top of that, he has three beautiful children and a wonderful wife, Catherine. What more could he want? Life isn't done with him yet. Out of the blue, his wife is diagnosed with cancer, and Quentin finds himself reeling. With Catherine so sick, his career no longer matters to him, and his father's invitation to Nantucket is looking more and more appealing. Maybe he should take his family out of the city for a while.

It's finally time for Carmella to marry the love of her life—her best friend turned boyfriend turned fiancé, Cody. As she grapples with her new role as stepmother to Gretchen, she learns some surprising news about her own situation and finds herself rewriting a future she'd once thought would be aimless and incredibly lonely.

A never-before-seen Christmas guest arrives to the island, filled with secrets of her own. The Sheridans welcome a brand-new baby. Complications arise left and right as the Sheridan sisters grapple with another season of changes. The Sheridan sisters’ mother, Anna Sheridan, never spoke much about her family, which is why the appearance of her younger sister is a surprise for all of them. She brings with her a host of troubles at the very worst time, as Audrey arrives home from a tumultuous semester at Penn State, just as Christine gives birth to her very first child.

Elsa's eldest, Cole Steel, is on the brink of the rest of his life. Like his father before him, he's a remarkable sailor—but unlike his father, he has no wife, no children, and just the open ocean at his feet. Elsa's not entirely pleased with his reckless nature. But she knows he has the same adventurous spirit his father always had. Aiden lives through Cole every day. Recently, Cole signed a contract to sail professionally. It's the opportunity of a lifetime—with a caveat. His boss is widely known as the toughest in the business.

Elsa's middle child, Mallory, is often described as the quietest and sweetest of all the Remington women—just as happy-go-lucky as Elsa, agreeable as Janine, and punctual as Nancy. Needless to say, it never pleased Mallory to be overlooked. But after her accidental pregnancy with her on-again, off-again boyfriend Lucas, plus the death of her father and grandfather in the span of a year, she's had very little time to ask herself that pivotal question: Who am I?

For the past twenty years, Lola Sheridan has worked tirelessly as a single mother to Audrey and a renowned journalist across the eastern seaboard. Now, she finds herself in a particularly strange and beautiful scenario. She’s fallen in love with the handsome Italian sailor, Tommy Gasbarro, and made a home with him on the Vineyard. But life circumstances are ever-shifting. And when Tommy pops a question Lola never imagined anyone would ask her, she is shocked.