Olivia Lupo feels stuck. All her friends have gone on to their first year of college while she's still at home with her family. There's a good reason though, her beloved grandmother, Annie, has dementia, and Olivia can't bear the thought of being so far from home when Annie needs her the most.

So when her stepmother asks the family to spend three weeks of the summer on Martha's Vineyard, Olivia plans to say no...until she discovers an old box Annie filled with photos and memories from her own time there. Olivia decides to follow in her grandmother's footsteps and spend some time on the island that Annie describes as magical.

When she arrives, she meets Connor, a boy from her past who really wants to be a part of her present... and future. Olivia's never thought about forever with someone until meeting Connor...and it scares her. How can she make plans when all she wants to do is keep close to her grandmother before she's gone forever? As she recreates the memories Annie made a lifetime ago, she has to decide if she's finally willing to give someone her heart, just when she needs it the most.