What Is Havana About?
The premise of Havana in 321 words, with nothing given away. The full story follows below.
In the waning days of the 1950s, Havana swirls with a restless energy that feels both intoxicating and precarious. The city’s glittering casinos sit beside crumbling colonial facades, while the rumble of revolution seeps through its streets like a low, omnipresent drum. Nights are alive with the clatter of chips, the hiss of cigarettes, and whispered promises of a new order that may topple the old‑world decadence at any moment.
Jack Weil arrives in this charged atmosphere with a reputation for taking risks that most would deem reckless. A seasoned gambler whose distrust of everyone around him is as sharp as the cards he plays, he is drawn to Havana not only by the lure of high‑stakes poker tables but also by the tantalizing promise of a quick, decisive win that could finally tip the scales in his favor. His confidence masks a deeper need to prove himself in a world where fortunes change as quickly as allegiances.
It is amid the smoky lounges and the fevered chatter of revolutionaries that Roberta Duran first crosses his path. Elegant, enigmatic, and married to a charismatic Communist leader, she embodies the dangerous allure that the city itself offers. Their connection crackles with forbidden intensity, pulling Jack into a delicate dance between personal desire and the volatile political currents swirling around them. The prospect of love becomes another high‑risk gamble, one that could cost far more than a single hand at the table.
The film balances the seductive pulse of Havana’s nightlife with the looming uncertainty of a nation on the brink of transformation. Tension hangs in the air like a half‑lit cigar, and every encounter feels charged with the possibility of both triumph and tragedy. As the stakes rise—both at the casino and in the streets—Jack’s world tilts ever closer to a point of no return, where the line between fortune and fate blurs beneath the rhythm of a revolution in full swing.
What Happens in Havana?
The complete story of Havana, from the first scene to the last, in 795 words (about 3 minutes). Spoilers throughout. Names in the text link to 1 cast member page.
Spoilers ahead
On Christmas Eve, 1958, as Cuba’s revolution edges toward its crescendo, Roberta Duran enlists the help of Jack Weil, Robert Redford, to smuggle radios for the insurgents hiding in the hills. Weil agrees only because he is drawn by a romantic interest in her, and the arrangement feels like a dangerous, glittering bargain. When they meet again for the promised payoff, Roberta reveals she is married, shattering Weil’s hopeful illusion and setting a precarious course through a world of risk and loyalty.
In Havana, Weil reconnects with a Cuban journalist acquaintance, and during a night on the town they unexpectedly cross paths with Roberta and her husband, Dr. Arturo Duran, a recognized revolutionary leader. Duran asks for Weil’s continued aid, but Weil, wary and overwhelmed, refuses to be drawn deeper into the conflict. This moment marks the uneasy blend of charm and duty that threads through Weil’s choices.
After a night of hedonistic excess, Weil learns from the newspapers that Duran has been arrested and killed, a blow that leaves him reeling yet still technically entangled in the game. He presses on with the poker schedule, a distraction that mingles with real danger when he meets the head of the secret police. The news of Roberta’s arrest and torture follows, and Weil uses leverage over a debt-ridden player to secure her release, a move that binds his fate to hers in increasingly intimate ways.
Roberta, shaken by danger and captivity, takes shelter in Weil’s apartment, then vanishes that afternoon, leaving Weil to confront the price of attachment in a country tearing itself apart. Realizing he has fallen in love with her, and buoyed by the encouragement of an old gambling friend, Weil ventures into Cuba’s interior to locate her at Duran’s old estate. He persuades Roberta to return with him to Havana and to leave the country together, even as he reveals a secret: a diamond concealed in a lump on his arm—insurance from a youth spent in risk and riskier gambles. Plans are set for her to depart by boat, but when Weil returns to the apartment he is confronted by two Cubans who inform him that Duran’s men want him to extract Roberta from the country.
A CIA acquaintance, Marion Chigwell, confirms that Duran is alive, and Weil uses that leverage to coerce Chigwell into assisting with the rescue. Posing as an agent, Weil visits Duran, who is being held by the chief of the secret police, and tells the officer that Washington intends to free Duran, offering a $50,000 payoff. To fund the rescue, Weil visits a doctor and a jeweler to convert the diamond into cash, all while telling Roberta that her husband is still alive. Overwhelmed by the deception and the stakes, Roberta departs to search for Duran herself.
Back at the casino, Weil dominates the big games with a blend of nerve and nerve-racking risk, and the casino’s manager, Joe Volpi, forgives him, recognizing that Weil’s primary aim has always been saving Roberta. As New Year’s Eve 1959 arrives, the revolution triumphs and the social order in Havana collapses in a chaotic exodus: the upper classes flee as the streets erupt in celebration, destruction, and renewal. Weil and Volpi decide it’s time to leave, yet the morning after finds Weil preparing to depart when Chigwell delivers a new, surprising line of work: he is told of a different book ahead. Roberta appears at the door, noticing the bandage on Weil’s arm and understanding the cost he paid to rescue her and her husband. She chooses to stay with the revolution, and Weil is deeply changed by the experience.
Four years pass. In 1963, Weil drives down to the Florida Keys, gazing out toward Havana and hoping to glimpse a boat carrying Roberta. He knows the ferry no longer runs, yet he continues the yearly vigil, a quiet testament to what Cuba’s upheaval did to him—and what it said about the rest of his life. The changes in Cuba echo across the United States, reminding Weil that escape is not the same as freedom, and that love, loyalty, and atonement can endure even as the world around them shifts beneath their feet.
- The tale is driven by the fragile thread between desire and duty, the lure of easy fortune, and the stubborn pull of a promise kept under impossible circumstances. The characters navigate a landscape where loyalties are tested, where wealth and power blur moral lines, and where a single act of courage can redefine a man’s future. The story leaves us with a mirrored image of departure and longing: a man who watches the horizon for a boat that may never return, and a woman who chooses a future rooted in a cause greater than any single plan.
Havana Timeline: Every Key Event in Order
12 key events in the order they happen, from “Roberta seeks radio smuggling help on Christmas Eve” to “The endurance of love and change”. 12 events name a place, across 8 locations.
- 1
Roberta seeks radio smuggling help on Christmas Eve
Roberta Duran asks Jack Weil to help smuggle radios for Cuban revolutionaries aboard the Miami to Havana crossing. Weil agrees, drawn to her romantically even as he understands the mission's danger. The pact sparks a fragile alliance that threads through the explosive events to come.
When:Christmas Eve 1958 Where:Aboard the boat from Miami to Havana
- 2
Havana rendezvous and a fateful encounter
Upon arriving in Havana, Weil encounters a Cuban journalist acquaintance, and during a night on the town they unexpectedly run into Roberta and her husband Arturo Duran. Duran asks Weil for continued aid to the cause, testing his loyalty. Weil declines, setting the stage for later tension.
When:December 1958 Where:Havana, Cuba
- 3
Roberta's arrest and Weil's uneasy moral twist
After a night of revelry, Weil reads a newspaper report that Arturo Duran has been arrested and killed. The shock pulls him into the underworld of the city as he learns Roberta has also been arrested and tortured. The personal stakes suddenly dwarf his earlier plans.
When:Late December 1958 Where:Havana, Cuba
- 4
Roberta sheltered, then vanishes
Weil engineers the release of Roberta by pressuring a fellow debtor to help, though the rescue is precarious. She is sheltered in his apartment, but she vanishes that afternoon, leaving Weil unsettled and more determined to find her. The events dramatize the cost of love and the risks of rebellion.
When:Late December 1958 Where:Weil's apartment, Havana
- 5
Weil pursues Roberta into Cuba's interior
Realizing he is in love with Roberta, Weil, spurred by an old gambling friend, travels deep into Cuba to locate her at Arturo Duran's former estate. He persuades her to return with him to Havana and to consider leaving the country. He reveals a diamond in his arm that he carries as a personal insurance in case of need.
When:Early 1959 Where:Duran's old estate, Cuba interior
- 6
Duran demands Roberta's exit; Chigwell is enlisted
Two Cuban men intercept Weil's return and inform him that Duran demands Roberta be taken out of the country. Weil then enlists Marion Chigwell, a CIA acquaintance, who confirms that Duran is alive and pushes him to help. He pressures Chigwell to cooperate in freeing Duran.
When:Early 1959 Where:Havana, Cuba
- 7
CIA masquerade and the bid to free Duran
Posing as a CIA operative, Weil visits Duran, who is being held by the chief of the secret police. He tells the chief that Washington wants Duran released for a payoff of $50,000. He funds the bribe by selling the diamond, visiting a doctor and a jeweler. He also tells Roberta that her husband is alive, prompting her to leave to find him.
When:Early 1959 Where:Secret police detention center; doctor and jeweler in Havana
- 8
Gambling and forgiveness on the casino floor
Weil shifts his focus to the casino, pulling off a big gamble that tests his nerves and finances. Joe Volpi, the casino manager, forgives him, understanding that his priority is saving Roberta rather than profit. The line between gambling risk and personal rescue blurs on the floor.
When:1959 Where:Havana Casino
- 9
New Year’s Eve 1959: revolution triumph
On New Year’s Eve, 1959, the revolutionaries win and Havana erupts in celebration as the old order scrambles to flee. The upper class abandons their luxury while the people trash the casinos in a spontaneous show of power. Weil and Volpi decide it is time to leave, even as their personal story remains unresolved.
When:December 31, 1959 Where:Havana, Cuba
- 10
A farewell in the morning light
The next morning, Weil sits in a Havana restaurant preparing to depart when Roberta appears to bid him farewell. She sees the bandage on his arm and realizes the price he paid to save her husband. She chooses to stay with the revolution, and Weil is forever changed by the ordeal.
When:January 1, 1960 Where:Havana restaurant
- 11
Four years later: longing across the sea
Four years later, in 1963, Jack drives to the Florida Keys and gazes toward Havana, hoping to glimpse a boat bringing Roberta. He knows the ferry no longer runs, yet he keeps the annual vigil as a symbol of longing and of Cuba's shifting fate. He recognizes that changes in Cuba are echoed in the United States.
When:1963 Where:Florida Keys, USA
- 12
The endurance of love and change
Roberta remains with the revolution, while Weil's experiences have left him a changed man. The ending underscores the collision of personal longing with political upheaval and hints that some bonds survive only in memory.
When:1960s Where:Havana, Cuba
Who Are the Main Characters in Havana?
4 characters, among them Jack Weil (Robert Redford), Roberta Duran (Lena Olin) and Arturo Duran (Raúl Juliá): who each one is and the part they play in the story. Every profile links to the actor’s page.
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Jack Weil (Robert Redford)
Played by Robert Redford
Jack Weil is a seasoned American gambler who arrives in Havana with a wry charm. He is pragmatic, risk-taking, and capable of bending rules to survive. His growing affection for Roberta becomes a catalyst for his transformation as he chooses risk for love and for others over self-interest.
- 🎩 Charming
- 💼 Gambler
- ❤️ Romantic
-
Roberta Duran (Lena Olin)
Played by Lena Olin
Roberta Duran is a determined revolutionary's wife who recruits Weil to smuggle radios for the movement. She reveals she is married, complicating their budding romance. Her capture, torture, and shifting loyalties test Weil and push her toward choosing the revolution or saving their relationship.
- 🎯 Determined
- 🕊️ Loyal
- 🧭 Calculating
- AD
Arturo Duran (Raúl Juliá)
Played by Raúl Juliá
A revolutionary leader and Roberta's husband, Arturo Duran embodies the movement's political stakes. His arrest and fate become a driving force for Weil’s actions and Roberta’s resolve, highlighting the personal cost of rebellion.
- 🔥 Revolutionary
- 🗡️ Determined
- 🎖️ Martyr
- MC
Marion Chigwell (Daniel Davis)
Played by Daniel Davis
Marion Chigwell is Weil's CIA contact, a capable liaison who confirms Duran’s survival. Weil then pressures her to help secure Duran’s release, drawing her into a high-stakes political effort where professional duty collides with personal risk.
- 🕵️♀️ CIA Liaison
- 🎭 Mysterious
- 🧭 Strategic
Where and When Is Havana Set?
Havana is set in Havana, Cuba, Miami, United States, Florida Keys, United States (1958-1959, 1963). Here is why the time and place matter to the story.
When
1958-1959, 1963
The principal events unfold on Christmas Eve 1958 through New Year’s Eve 1959, as Cuba's revolution intensifies and key figures are drawn into peril. Four years later, in 1963, the narrative shifts to Weil’s longing from the Florida Keys, with Havana still in sight but the country forever altered. The period anchors a romance amid political upheaval and a country on the cusp of dramatic change.
Where
Havana, Cuba, Miami, United States, Florida Keys, United States
Set predominantly in Havana, a bustling port city that sits at the crossroads of wealth, crime, and revolution. The story follows a tense journey beginning with a ship from Miami to Havana, and unfolds across casino streets and revolutionary hills. The Florida Keys serve as a brief backdrop for Weil’s longing and the broader exile looming over the characters.
- 🗺️ Havana
- 🇨🇺 Cuba
- 🏝️ Caribbean setting
What Are the Themes of Havana?
3 ideas the story keeps returning to, among them Love vs Duty, Gambling and Morality and Revolution and Escape.
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01
Love vs Duty
A romance blossoms between Weil and Roberta, pulling him into a dangerous mission. He must choose between personal happiness and a sense of responsibility to the revolution. The escalating political conflict tests loyalties and reshapes what each character is willing to sacrifice. In the end, love and duty redefine one another rather than resolve simply.
-
02
Gambling and Morality
Gambling serves as both metaphor and mechanism for moving through danger, as Weil leverages bets and bravado to protect allies and outmaneuver powerful enemies. The casino world blurs lines between risk and ethics, pushing Weil to confront what he’s willing to lose for others. The stakes extend beyond money to freedom, life, and political responsibility.
-
03
Revolution and Escape
The Cuban revolution frames the characters’ choices, turning personal risk into collective action. The escape from Cuba becomes a driving force for Weil, Roberta, and their allies, highlighting the lure and peril of leaving a homeland behind. The era’s upheaval casts a long shadow over loyalties, identity, and future possibilities.
What Kind of Film Is Havana?
Tense in tone, with steady pacing and a moderate story, going by the plot summary.
- Tone
- Tense
- Pacing
- Steady
- Story
- Moderate
- Intensity
- High
- Ending
- Bittersweet
A tense and passionate romantic drama set against the backdrop of the Cuban Revolution, creating a feverish atmosphere of dangerous allure, high-stakes choices, and a melancholic sense of loss for a world on the brink of collapse.
- tense
- romantic
- dangerous
- melancholic
- feverish
- political
- forbidden love
- political revolution
- gambling
- espionage
Content notes: torture, political violence, death, arrest.
Quiz
How well do you remember Havana? Test yourself on the story.
Where to Watch Havana
Rent or buy it from Amazon Video and Apple TV Store. US availability and prices from JustWatch.
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