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The Best Boating & Sailing Movies to Keep you Afloat on Rainy Days

Post by Becky at Dockwa - Published on 7/26/21 9:12 AM
We’ve all endured our fair share of sun and rain this season. As spring ends and summer begins, for some of us, it feels as though fall approaches quicker every year, especially when the weather doesn't cooperate. While there is only so much time left for Northern boaters to enjoy whatever days we have left to spend on our boats, that doesn't mean we should let the rain stop our fun.

Here's our list of favorite boating and sailing movies to get us through any cloud-covered days! From the classics to documentaries, family-friendly flicks, and more–this list has it all! So batten down the hatches, grab the popcorn, and pop in a movie to find your next high seas adventure off the water.



Boating and Sailing: The Classics

Moby Dick (1956)

In this film adaptation of Herman Melville's classic novel, Moby Dick, Captain Ahab (Gregory Peck) seeks revenge on a great white whale that once maimed him. Set in New England, Captain Ahab's obsession with the whale leads his crew into grave danger. If you prefer to see an updated version of this classic, In the Heart of the Sea (2015) stars Chris Hemsworth, Tom Holland, Benjamin Walker, and Cillian Murphy.

The Old Man and the Sea (1958)

An adaptation of Ernest Hemingway's novella, "The Old Man and the Sea" features Spencer Tracy as The Old Man, a Cuban fisherman who hasn't caught a fish in 84 days. On the 85th day, his luck changes once he hooks a huge marlin, which he then battles with for three days to bring back to shore. 


Mutiny on the Bounty (1962)

Based upon a real 1795 mutiny, Fletcher Christian (Marlon Brando) leads the crew of the H.M.S. Bounty in a mutiny against the sadistic Captain Bligh in this historical drama. 

Wind (1992)

In more than 140 years of competition, the United States has lost the America's Cup only once. “Wind” is the dramatic, fictional story of a group of American challengers whose drive to win back sailing's top prize plunges them into a world where money, power, love, and ambition intertwined. 

White Squall (1996)

This coming-of-age story features Dr. Sheldon “Skipper” (Jeff Bridges) as he leads a crew of teenage boys on the voyage of a lifetime, which test their skills as they face an unexpected storm. 

Master and Commander: The Far Side of the World (2003)

Set during the Napoleonic Wars, this historical drama is adapted from the Aubrey-Martin book series written by Patrick O'Brian. Captain Jack Aubrey (Russell Crowe) of HMS Surprise must lead his crew to capture a powerful French vessel of the coast of South America. 





Boating and Sailing Comedies 

One Crazy Summer (1986)

Set on Nantucket Island, Hoops (John Cusack) must write and illustrate a love story in order to gain admittance into art school. In an effort to impress the girl of his dreams, he enters a sailing regatta despite his fear of the ocean. Hoops’ crazy summer adventures serve as inspiration for his story. 


Overboard (1987)

Joanna (Goldie Hawn), a wealthy heiress, hires Dean (Kurt Russell), a carpenter who she mistreats and takes advantage of. Joanna sets sail on her yacht, leaving the carpenter unpaid for his work. After falling overboard at sea, she is diagnosed with amnesia and Dean finds a creative solution to his money problems. 

Captain Ron (1992)

This gem is perhaps the most notorious of cult classics for sailors. A suburban family from Chicago hires Captain Ron (Kurt Russell), a laid back and unconventional Navy veteran, to sail them around the Caribbean. This comedy will have the whole family laughing as their adventure unfolds. 

Waterworld (1995)

In this futuristic thriller, the majority of Earth’s land has been submerged under melted polar ice caps. The human race struggles to survive on dilapidated boats and makeshift floating cities. Fun Fact: Waterworld was the most expensive movie made at the time. 


The Life Aquatic with Steve Zissou (2004)

Steve Zissou (Bill Murray), an eccentric oceanographer, loses his partner to a deadly jaguar shark attack while filming his latest documentary. For his next project, Zissou gathers a group of friends and sets out on a mission to document the shark’s demise. As a Wes Anderson film, “The Life Aquatic” includes many standard Wes Anderson characteristics: a peculiar color palette, an all-star cast, and quirky characters with dysfunctional relationships. 

Pirate Radio (2009)

This British comedy tells the story of a pirate radio station that broadcasts from a ship anchored in the North Sea. Despite the genre being heavily censored by the government, the station plays pop and rock music that inspired the 60’s generation.



Boating Movies Based on a True Story


Titanic (1997)

Based on the true story of the sunken RMS Titanic, this classic movie stars Leonardo DiCaprio and Kate Winslet who portray young lovers traveling aboard the ill-fated ship.

The Perfect Storm (2000)

Billy Tyne (George Clooney) insists that his crew go out on one last fishing trip before winter sets in. Unbeknownst to them, a brutal storm is slowly gaining steam. Based off of the nonfiction book by Sebastian Junger, “The Perfect Storm.”

Kon Tiki (2012)

Legendary Norwegian ethnographer and explorer Thor Heyerdahl hypothesized that South Americans settled in Polynesia in pre-Columbian times. In order to prove his theory, Heyerdahl set out on an epic 4,300 mile crossing of the Pacific on a wooden raft named Kon Tiki in 1947. 

Captain Phillips (2013)

Tom Hanks stars as the eponymous hero in this thriller based on a real-life hijacking of the MV Maersk Alabama by Somali Pirates.

The Mercy (2018)

“The Mercy” relays the incredible story of amateur sailor Donald Crowhurst as he attempts to solo circumnavigate the globe in the first race of its kind: The 1968 Sunday Times Golden Globe Race. 

Adrift (2018)

Shailene Woodley and Sam Claflin star as a couple who sail from Tahiti to Hawaii aboard a sailing yacht named Hazaña. Based on a true story, the film shows how the characters deal with life at sea after a hurricane passes through their path.



Family-Friendly Boating and Sailing Movies

Hook (1991) 

When Captain Hook kidnaps adult Peter Pan’s children, Peter must return to Neverland and reclaim his youthful spirit in order to challenge his old enemy. Packed with A-list stars Robin Williams, Dustin Hoffman, Julia Roberts and Maggie Smith, Hook is a family classic you can’t skip!


Pirates of the Caribbean: Curse of the Black Pearl (2003)

Packed with stars, this Disney film is one of our family movie favorites. Captain Jack Sparrow (Johnny Depp) and blacksmith, Will Turner (Orlando Bloom) pair up to rescue the Governor's daughter, Elizabeth Swann (Keira Knightley) from the cursed pirate ship, The Black Pearl, which is under the command of  the wicked Captain Barbossa (Geoffery Rush).

Life of Pi (2012) 

After a cataclysmic shipwreck, an Indian boy named Pi finds himself stranded on a lifeboat with a ferocious Bengal tiger. Together they face nature's majestic grandeur and fury on an epic journey of discovery. 

Moana (2016) 

In this Disney animated film, Moana sets sail on a daring mission bestowed upon her by the ocean itself, to save her Polynesian village. Along the way, she meets the once mighty demigod Maui. Together they cross the ocean on a fun-filled, action-packed voyage. 



Boating and Sailing Horror Movies

Jaws (1975)

When a killer shark unleashes chaos on a beach resort, it's up to a local sheriff, a marine biologist, and an old seafarer to hunt the beast down. 

Dead Calm (1989)

After the sudden death of their son, an Australian couple decides to cope with their grief at sea. Along the way they pick up a mysterious lone survivor of a shipwreck. This psychological thriller leads both the husband and wife into grave danger in their efforts to uncover the truth about the shipwreck. 

Ghost Ship (2002)

In a remote region of the Bering Sea, a marine salvage crew discovers the eerie remains of a passenger liner that went missing more than 40 years ago. 

Open Water 2: Adrift (2006)

This psychological horror features five friends who struggle to get back onto their yacht after forgetting to lower down a swim ladder. Two diving masks, a knife, and a toy inflatable are the only tools they have to save themselves from their demise.



Boating and Sailing Documentaries

The Endurance (2000)

Named after his ship, “The Endurance” retells the legendary adventure of Sir Ernest Shackelton along with his 28-man crew and their ill-fated expedition to Antarctica from 1914-1916. Original footage of the voyage as well as interviews with surviving crew members no doubt aided in the success of this documentary. 

Racing Around the World Alone (2010)

Thirty skippers compete to be the fastest person to solo circumnavigate non-stop and with no assistance around the globe in the 2008/2009 Vendée Globe. In one of the most challenging and dangerous races of all time, weather is not the only factor that could sabotage their journey. 

Red Dot on the Ocean: The Matt Rutherford Story (2014)

Matt Rutherford was considered an “at-risk” youth, suffering from ADHD and drug abuse, when he decided to change his life’s course by sailing non-stop single-handedly around the Americas. Labeled a “suicide mission” by many seasoned sailors, Rutherford achieved the unexpected.

The Weekend Sailor (2016)

In 1974, Mexico native Ramon Carlín entered his yacht Sayula II into the first crewed around the world sailing race. With little experience and a crew comprised of his family and friends, Carlín beat all odds and won this prestigious race, today known as The Volvo Ocean Race. 


What are some of your favorite can’t miss boating movies? Let us know by sharing in our Facebook Group. Stay up to date with all things Dockwa and more on our blog and join the conversation on Facebook, Twitter, and Instagram.

This post has been updated and republished to include current information.



Post by Becky at Dockwa

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