Most swashbucklers have a leading lady who functions almost purely as a love interest for the hero, a trope that is half-mocked and half-embraced in The Princess Bride, and wholeheartedly adopted in almost everything else, like the pretty island girls in Mutiny on the Bounty, though in that case, the girls might be more adequately described as sex toys. There are also more than a few swashbucklers that have no female speaking parts, or no female parts at all - one thinks of Master and Commander: The Far Side of the World. But, search long enough and there are some great female characters, swashing and buckling alongside of the men. None of the women on this list are genuinely feminist, but their presence alleviates the extreme phallocentrism of the genre.
Elizabeth Swann (Keira Knightley) - Pirates of the Caribbean (2003, 2006, 2007)
I was more than a little tempted to leave Elizabeth Swann off of this list. Don't get me wrong - I love the Pirates of the Caribbean movies. I could watch them all day (and I have). The problem is that the character of Elizabeth (as well as the latest female lead, Angelica, played by Penelope Cruz) panders to politically correct ideas about female empowerment without rejecting the stubborn misogyny of gender politics in mainstream cinema. Elizabeth is a strong fighter, who by the end of the first movie is fully capable of rescuing herself as well as rescuing others - though the action of the first film is predicated on a damsel in distress scenario - and she even moonlights as a pirate captain, fully capable of being a leader in battle and at sea. What's frustrating is the ending - the pirates win, her true love Will is now an immortal only able to touch land once every nine years, and Elizabeth, the battle-hardened adventuress - what does she do? She sets up house on an apparently deserted island, barefoot and pregnant, waiting for her husband to come back. In nine years. In other words, Elizabeth is awesome until she has the chance to get married. There would have been an easy way to fix this. Will is off doing his job; why couldn't Elizabeth go off, doing what pirates do best? The answer - that would mean that Elizabeth actually is an empowered, independent woman, rather than an aspiring housewife who did all that badass stuff because marketing polls indicated that teenage boys think girls with swords are cool.
Arabella Bishop (Olivia de Havilland) - Captain Blood (1935)
In this, one of the greatest swashbucklers of all time, Arabella Bishop is the stunningly beautiful niece of the military commander of Port Royal. Captain Blood (Errol Flynn) is a doctor, caught giving medical care to a wounded rebel during the Monmouth Rebellion and sentenced to transportation and slavery, who catches the eye of Arabella. She buys him as an act of mercy, finding his forceful personality attractive and recognizing that it could cost him his life. Blood is resentful that he has been rescued by a woman, all the more so because he's in love with her. The balance of power inevitably changes and later, when Arabella has been taken prisoner by another pirate (Basil Rathbone, an actor who literally never gave a bad performance), Blood buys her, half to rescue her and half in retaliation for having been purchased himself, earlier in the film. Arabella never lifts a sword in this film, nor she does take command of a ship, but she is a shrewd politician and without her favors, our hero would never have been one. The fact that Blood can't really rest until he's readjusted the power differential is yet one more aspect of the deeply patriarchal politics at play in swashbucklers. Arabella may not be a feminist, but she's a strong, intelligent, politically savvy woman - and, let's be frank, there aren't that many such characters in films today, almost eighty years later.
Roberta (Janet Munro) - The Swiss Family Robinson (1960)
This film, one of Disney's finest live action films, is about a shipwrecked Swiss family who create a home in their idyllic island paradise, only for pirates to attack. The pirates attack because the family has rescued their prisoner, Roberta, a young woman who had disguised herself as a cabin boy when captured. The two older sons, Fritz and Ernst, are both enamored of her as soon as her sex is discovered, and their already contentious relationship becomes even more so as a result of their rivalry. Roberta is a proper young lady from London, far more used to dancing at a ball than battling an anaconda or shooting murderous pirates. And that's why she's such a wonderful character. Roberta starts out with almost no survival skills and by the end of the movie, she rides a zebra, holds her own against pirates, asserts herself sexually and romantically, and even teaches Ernst a thing or two about shooting a rifle. Again, Roberta's no feminist, but she develops strength, independence, and ingenuity in the course of her adventures.
Manuela Alva (Judy Garland) - The Pirate (1948)
In this Caribbean musical fantasy, the incomparable Judy Garland plays Manuela, a young woman whose fantasies are aroused by tales about the legendary pirate captain Macoco. Gene Kelly plays an unscrupulous womanizing traveling acrobat, Serafin, who decides to impersonate the pirate of Manuela's dreams in an attempt to get her into bed ("marriage" is really a euphemism in this movie). The most revolutionary aspect of Manuela's character is her unabashed sexuality, expressed both in her fantasies, dramatized in dance and featuring Kelly in some of the most flamboyantly sexy choreography in a Hollywood musical, and in the song, "Mack the Black." If she was easily swept off her feet, she would however be an unremarkable heroine - but she's not. Her discovery of Serafin's treachery results in a brawl of epic proportions, during which Serafin is made to realize he's certainly met his match. At least in an oblique way, this film - made in 1948 - examines female sexuality and sexual fantasy and it allows its heroine surprising latitude to be bold, sexually and physically.
Sorsha (Joanne Whalley) - Willow (1988)
Sorsha, daughter of the evil Queen Bavmorda, is a hard-as-nails military commander, ambitious, brutal, brave, and an expert with a sword. In the course of the film, she - of course - experiences a romantic and sexual awakening, which also awakens her sympathies for the just cause against her mother. It's worth noting that, although there is a misogynistic element to her political re-education, especially since it's achieved by "reminding" her that she's female a.k.a. sexual, she falls for a man (Val Kilmer) equally battle-hardened and even better with a sword. Though Madmartigan - yes, that's his name and you can thank George Lucas for that - is better, he's only slightly better, and he generally treats Sorsha as an equal in military situations, respecting her ability to take care of herself (and quite a few enemies to boot). Sorsha is undoubtedly one of the most awesome women in any fantasy film or swashbuckler.
Maid Jean (Glynis Johns) - The Court Jester (1955)
The Court Jester is a brilliantly funny send-up of swashbucklers and Arthurian epics. Danny Kaye stars as the jester, Hubert, eager to take up arms to restore the true king to the throne. He's in love with Maid Jean, his superior in the resistance and an acute military commander. She isn't at the top of the heap, but she's certainly in the upper echelons of command. Played by the lovely Glynis Johns, Maid Jean is a whip-smart political player, protecting the inept jester, rather than being protected by him. The true king is a mere infant and one would typically expect Maid Jean to be the royal caretaker, given her sex, but instead it is Hubert who is assigned childcare, from singing lullabies to changing diapers. When her sex makes her vulnerable, as in the scenes in which she is captured as a "present" for the royal pretender, she makes her weakness a strength, taking advantage of her access to the royal chambers and inventing a terrible contagious familial disease that keeps her potential rapist at arm's length. But, really, what gives Maid Jean a feminist edge is the fact that she is dominant in her romantic relationship, protecting rather than being protected, ordering rather than being ordered.
Maid Marian (Olivia de Havilland) - The Adventures of Robin Hood (1938)
The Adventures of Robin Hood is the greatest swashbuckler ever made and the film that crystallized our modern pop culture conception of the Robin Hood legend. In most Robin Hood movies, Maid Marian is a damsel in distress, a helpless girl enamored of the handsome outlaw, but utterly unable to do much of anything but await rescue. Not so as played by Olivia de Havilland in this, the definitive version. While in all versions Maid Marian has relative importance as a marriage object and a means of forging political alliances, in this one, she is active in politics. Her politics are not swayed by her attraction to Robin Hood, but rather by the terrible suffering of the people he shelters in Sherwood Forest. Her compassion and intelligence change her politics and only then does she allow herself to acknowledge her love for the outlaw. Maid Marian also works as a spy from within Prince John's castle and when she is caught she bravely acknowledges what she has done and faces the penalty - death - without tears or pleading. Her bravery and her capability, her refusal to stay passive in the face of injustice, her assertiveness, all make her the most awesome female character in the swashbuckler genre.