Dynamic Watchlist Hub: Jan 19, 2026

10 Best Movies Like Sailing Into Love

If you loved Sailing Into Love, we've curated the perfect watchlist for you based on shared genres, themes, and directorial style.

🏆

Expert Review & Ratings

See our full critical analysis and audience score for Sailing Into Love.

View Review →
#1
Love by Chance

Love by Chance

2016★ 6.0

Why watch this? A perfect follow-up to Sailing Into Love for fans of Romance & TV Movie. It captures a similar heartwarming atmosphere.

Claire, an ambitious pastry chef, is busy running her new restaurant, but her meddling mom is preoccupied with her lack of love life. Without her knowledge, Claire’s mother finds h...

#2
Love in the Sun

Love in the Sun

2019★ 6.1

Why watch this? A perfect follow-up to Sailing Into Love for fans of Romance & TV Movie. It captures a similar heartwarming atmosphere.

When successful dating app creator Alana hesitantly gets engaged, she returns to her hometown in Florida to deliver the news to her dad. Upon returning home, she crosses paths with...

#3
Tulips in Spring

Tulips in Spring

2016★ 5.9

Why watch this? A perfect follow-up to Sailing Into Love for fans of Romance & TV Movie. It captures a similar emotionally gripping atmosphere.

At Payden Farms, Rose meets Tom Novak — a handsome “flower broker” who acts as a liaison between the farm and local distributors — and discovers that the farm is faltering financia...

#4
All Yours

All Yours

2016★ 5.7

Why watch this? A perfect follow-up to Sailing Into Love for fans of Romance & TV Movie. It captures a similar light-hearted atmosphere.

Cass, a high-powered attorney and single mother of two, is on the hunt for a new nanny after her precocious kids ran off the last one....

#5
Winter Love Story

Winter Love Story

2019★ 6.8

Why watch this? A perfect follow-up to Sailing Into Love for fans of Romance & TV Movie. It captures a similar heartwarming atmosphere.

When new author Cassie is paired with successful author Elliot on a promotional book tour, she learns to believe in her talent. She also finds truth in the old adage “you can’t jud...

#6
From Friend to Fiancé

From Friend to Fiancé

2019★ 6.1

Why watch this? A perfect follow-up to Sailing Into Love for fans of Romance & TV Movie. It captures a similar heartwarming atmosphere.

When Ted gets engaged to the high school mean girl and asks Jess, his childhood best friend, to plan their wedding, things get complicated. Her true feelings for Ted keep getting i...