The fall boat shows have come and gone, winter is settling in, and sailing may seem like a distant dream as you hold your breath until your warm-weather Christmas charter.
All is not lost, though, as this is also a great time to both distract yourself and work on creating some cohesive group dynamics prior to your arrival at the charter base. Maybe your brother isn’t much of a sailor. Maybe no one has met the cousin’s new boyfriend. Who knows what drama awaits? Inject some excitement, anticipation and common experience into your group with a few nautical movie nights. Here are 10 films that are bound to get the group talking, laughing and asking questions as you wait on that delayed flight to paradise.
White Squall — Not exactly a chuckle fest, White Squall is based on a real tragedy from the 1960s, with Jeff Bridges as the stalwart captain in charge of a bunch of wealthy newbie sailors who relies on discipline to keep an orderly ship. Take notes if you need tactics to manage an unruly crew.
Wind — Racers Mathew Modine and Jennifer Grey act their hearts out in this tale of competitive drama. The plot is thin, but the cinematography is mesmerizing. Use this film if you want the group to consider actually sailing for speed rather than as a way to get to the next cocktail.
Dead Calm — Nicole Kidman and Sam Neill cruise a remote stretch of the South Pacific and come across the evil Billy Zane. Quiz the group about the completely improbably scenarios, sailing inaccuracies and Kidman’s bizarre hair.
Captains Courageous — This 1937 classic tells the story of a spoiled rich kid who ends up on a fishing schooner and learns the value of hard work. This may well be the best introduction to boat life your crew could have.
Jaws — This one is just to freak out your sister and maybe scare the kids enough to get them out of the water at the end of the day. Spielberg’s major directorial debut couldn’t be more iconic, and quotes from it can be entertaining at happy hour.
The Mercy — A fictionalized tale of the very real and very disturbed Donald Crowhurst, this 2017 film centers on the first around-alone nonstop race. Use this film to put the rigors of sailing in context. Having to wash dishes on a charter pales in comparison to facing the open ocean alone and may well provide perspective on shipboard complaints.
Captain Ron — Mandatory watching for any sailor, Captain Ron with Kurt Russell is remarkably accurate from a technical standpoint except for one glaring piece of silliness as it relates to sailboats. Ask your group to spot it. Bonus points go to the one who memorizes the most lines, which will appeal to the more competitive types in your group.
Adrift — A fairly accurate account of a cruising couple whose boat is dismasted after sailing into a hurricane, Adrift is based on a true story. Shailene Woodley does an impressive acting job in this tale, which ends with a major twist. Skip this one if you ever want your significant other to go long-distance cruising with you.
Maiden — A fascinating 2019 documentary about Tracy Edwards and her all-woman crew in the 1989 Whitbread Round the World Race. For sheer grit (and to get the girls in your group riled up) you can’t beat this true-life story.
All Is Lost — Completely the opposite of the factually correct Maiden is Robert Redford’s absurd All is Lost. Use this sheer bumbling nonsense as a quiz on how to (and not to) actually sail. Consider extra credit for anyone who stays awake through this bit of foolishness.
Use these and any other movies you can think of as an excuse to gather prior to your charter. Create a game out of each on movie night, both to serve as an icebreaker and to build anticipation until the charter itself. Not only will you catch onto any group issues, you’ll also learn how to better set and manage expectations. You’ll learn who’s naturally dramatic, who always lends a helping hand, who knows enough to be your go-to mate and what that new boyfriend is like. And if no one wants to play, then just enjoy these on your own as you’re waiting to get back under sail once more.