Dynamic Watchlist Hub: May 11, 2026

10 Best Movies Like Up in the Sky

If you loved Up in the Sky, we've curated the perfect watchlist for you based on shared genres, themes, and directorial style.

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Expert Review & Ratings

See our full critical analysis and audience score for Up in the Sky.

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#1
Free Rein: Valentine's Day

Free Rein: Valentine's Day

2019★ 7.5

Why watch this? A perfect follow-up to Up in the Sky for fans of Romance & Family. It captures a similar heartwarming atmosphere.

Love is in the air as Zoe and friends go on a quest to find a fabled Maid's Stone. But when rivalry blinds them to danger, it's Raven to the rescue!...

#2
Attraction

Attraction

2001★ 6.9

Why watch this? A perfect follow-up to Up in the Sky for fans of Romance. It captures a similar heartwarming atmosphere.

A writer/radio advice show host fails to heed his own advice as he stalks his ex-girlfriend and then becomes involved with an actress friend of hers....

#3
Sailing Into Love

Sailing Into Love

2019★ 6.9

Why watch this? A perfect follow-up to Up in the Sky for fans of Romance. It captures a similar heartwarming atmosphere.

A biology teacher’s crusade to save a nearby island from development leads to unexpected romance with the handsome and mysterious young sea captain who is new to the seaside town o...

#4
Holiday Date

Holiday Date

2019★ 6.5

Why watch this? A perfect follow-up to Up in the Sky for fans of Romance. It captures a similar heartwarming atmosphere.

When Brooke’s boyfriend, Ethan, breaks up with her just before the holidays, she agrees to go home with Joel, an actor who will pose as her boyfriend....

#5
Secret Millionaire

Secret Millionaire

2018★ 6.5

Why watch this? A perfect follow-up to Up in the Sky for fans of Romance. It captures a similar heartwarming atmosphere.

When a bored millionaire (Steve Lund) is mistaken for a parking attendant by a beautiful girl (Siobhan Williams) who is protesting against his family’s intention of closing a local...

#6
Matching Hearts

Matching Hearts

2020★ 6.5

Why watch this? A perfect follow-up to Up in the Sky for fans of Romance. It captures a similar heartwarming atmosphere.

As Valentine's Day nears, a matchmaker is tasked by her mentor to find a match for an entrepreneur who believes staying single is the key to success....

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