Don Antonio
Don Antonio, a Spanish nobleman and the wealthy son of a Viceroy of Spain, has been betrothed to Florinda through an agreement with his good friend, Florinda's brother, Don Pedro. However, Don Antonio is intrigued with the courtesan, Angellica. It is apparent that if he marries Florinda as planned, he will keep Angellica as a mistress, too. Don Antonio fights with the English gentlemen over the right to visit Angellica and is wounded by Willmore in a brawl. Eventually, Don Antonio gives up his claim on Florinda and forms a bond with Angellica, whom he nobly undertakes to support after her career as a courtesan is ruined.

Colonel Belvile
Belvile is an honorable and steadfast English colonel who fell in love with Florinda when he protected her from an attack during the siege of Pamplona. Belvile is one of many exiled Englishmen traveling around Europe during the Interregnum, the period after the beheading of Charles I and before the reinstatement of his son, Charles II. Unlike his English fellows, Belvile is not interested in any of the many courtesans in Naples, but pines away for his true love. He hopes to find her in Naples and marry her. However, it is Belvile's bad luck to get himself into countless situations that make it difficult for him to meet Florinda and elope with her as they had planned.

Angellica Bianca
Angellica is a famous courtesan who at the time of the play's events has just lost her benefactor, Don Pedro's wealthy uncle, who had been paying her monthly expenses of 1,000 crowns. Now she is advertising for a new lover, so she has placed three portraits of herself on the outside of her palatial home, along with the price. Angellica is accustomed to a life of luxury, but she has paid for it by sacrificing her honor and virginity for the riches she extracts from the men who fall prey to her seductive beauty. For Angellica, being a courtesan is a matter of survival and independence; to fall in love would ruin her, for then she would be at the mercy of the men she uses. Unfortunately, she falls hopelessly in love with one of the worst sort of men, Captain Willmore, who wants only physical satisfaction and not a love relationship. After being "undone'' by Willmore, Don Antonio graciously offers to be her lifelong companion, thus removing her from the need to market her body.

Ned Blunt
Blunt is a country gentleman and not as sophisticated as his friend Belvile. His favorite oath, "adsheartlikins," gives him away as a landed country bumpkin, a stock character. Blunt foolishly believes that a courtesan has fallen in love with his manly physique, and thus he proves an easy mark for her ruse to take him to her house and defrock him of his valuables and clothing. Blunt fears that his friends will laugh at him for his misfortune, since he had bragged overmuch of his conquest before he went with the "wench." This fuels his desire for revenge, which he nearly takes upon Florinda, the next woman he meets in the street, whom he mistakes for a harlot and whom he intends to rape brutally to avenge his wounded pride. When his friends do in fact laugh at him, Blunt goes into a rage, spluttering that he is "not an ass to be laughed at.’’ He lacks their gentlemanly power of restraint and decorum. Blunt is further humiliated when, ironically, a local tailor sews him a Spanish costume, ‘‘the mode of a nation [he] abominate[s],’’ instead of a "proper" English one.

Callis
Callis is governess to Florinda and Hellena. She is sympathetic to their plights, and so she willingly assists them in deceiving their brother, Don Pedro, so that they can enjoy the carnival in Naples. They are not so loyal to her, however, for when Florinda decides to run away from her brother's home to find and marry Belvile, Valeria pushes Callis into a chest and locks her in to give Florinda time to escape. Neither Florinda nor Hellena shows any remorse for this subterfuge.

Florinda
Florinda is the only pure and innocent young woman in the play. Florinda is a noblewoman who has been betrothed to wizened old Don Vincentio by her father, but since she and her sister and brother are away in Naples, she has been able to put this out of her mind. In the meantime, she has fallen in love with the English Colonel Belvile, who protected her and her brother when they were besieged in Pamplona and whom she hopes to marry. Her brother, however, has different plans. Being out of the purview of their father, he hopes to confer his sister and her sizeable dowry on his friend, Don Antonio. Don Pedro thinks his plan will please his sister, since Don Antonio is young and handsome. To this plan Florinda is blithely unaware, until she gets a rude awakening when her brother announces that she must marry Don Antonio the next day. Thus Florinda is willing to accompany her more adventurous sister Hellena in a final night on the town, so that they each can experience a taste of love, and so that Florinda can hopefully speak to Belvile of her plight. During their adventure, Florinda is twice nearly raped, first by a drunken Willmore and then by Blunt, bent on revenge against women in general and harlots in particular.

Frederick
Frederick is an English gentleman and friend to Belvile and Ned Blunt. Frederick shares Blunt's anger at the courtesans of Naples who strip Blunt of his belongings and his clothes. Thus, he is easily convinced to help Blunt rape the innocent Florinda in revenge, when they mistake her for a whore. However, he convinces Blunt to stop when Florinda mentions that she knows Belvile, and thus proves she is a "maid of quality'' and not a harlot.

Hellena
Florinda's younger sister, lively Hellena, is destined for the nunnery, a common destination for younger sisters since the Medieval period. Before being carted off to a life of devotion devoid of men and fun, Hellena intends to spend an evening on the town in Naples searching for "a saint of [her] own to pray to,’’ so that she can experience the "sighs" and "wishes" of being in love. She and her sister don masks and colorful clothing so that they can masquerade as courtesans and flirt openly in this society that frowns on such behavior from "women of quality.'' Hellena feels confident in her ability to play with love and not be smitten, but smitten she is, by the quintessential rover himself, Captain Willmore. Both of them espouse a policy of loving and leaving, and in this they prove a perfect match for each other. So perfect is their match that even the dour Don Pedro approves their marriage, and therefore Hellena does not have to cloister herself in a nunnery after all.

Lucetta
Lucetta is a common whore who seduces the naïve Ned Blunt into meeting her at her house to consummate their passion. He fails to recognize the harlot's trick, and she gets him to remove all of his clothes while she steals out of the room and locks him in it. Although she enjoys stealing his belongings, she expresses some regret that he did not at least get a chance to enjoy her favors before he was stripped of his possessions. Her paramour, Phillipo, has no such regrets and in fact finds his passions inflamed by the thought of her being with another man.

Moretta
Moretta is Angellica' s servant and is herself a courtesan to less wealthy patrons. Moretta tries to steer Angellica away from Willmore, for she sees that he does not have a noble heart. Her warnings go unwarranted and unwelcome.

Don Pedro
Don Pedro is a Spanish nobleman who has been left in charge of his two sisters in their father's absence. Don Pedro follows the European tradition of marrying off the older sister, Florinda, and committing his younger sister, Hellena, to the nunnery. Florinda's sizable dowry makes her an excellent gift for his good friend, Don Antonio. Don Pedro tries to protect his sisters' virginity by keeping them out of society.

Phillipo
Lover of the whore, Lucetta, Phillipo feels fully justified in bilking an Englishman due to the long rivalry between Spain and England. The idea that Lucetta nearly went to bed with Blunt makes Phillipo feel "wanton," so he goes to bed with her himself.

Sancho
Lucetta's pimp, Sancho, leads the naïve Blunt to Lucetta's house for what Blunt thinks will be an amorous tryst, but which Sancho knows will be his undoing.

Valeria
Valeria, whose name connotes the Latin-based word "valiant," is cousin to Florinda and Hellena. Valeria finds the costumes and masks that the three of them wear to disguise their noblewoman's demeanor and masquerade as courtesans. Valeria falls in love with the English gentleman, Frederick, and they marry at the end of the play.

Captain Willmore
Captain Willmore, the rover, is an English sailor traveling with the exiled Prince (Charles II), and who is on leave after many months at sea without any women. A man without a conscience, Willmore wants nothing more than to enjoy the pleasures of as many women as possible during his brief stay in Naples. Willmore is a smooth talker who charms both lady and courtesan, and he repeatedly manages to earn back their love even after they catch him in another tryst. Nor does he scruple to take their money. While drunk, he attempts to rape a noblewoman. He meets his match in Hellena, who shares his appetite for adventure and love and whose streak of bold independence may inspire him to fidelity.