The dynamic world of 18th-century Europe was filled with energy, new ideas, elegant royal courts, luxury, and intrigue. The masqueraders in this Venetian gambling establishment give a hint of the era’s elegance, merriment, and mischief: mirrors reflect the grand surroundings—its paintings and glittering fabric-covered walls—as well as the festive company. The revelers are clothed in sumptuous costumes and have concealed their identities with masks. Their dress and demeanor reveal the period’s fascination with theatricality and artifice. How best to unmask this intriguing century of fast-growing cities, increasing geographical and social mobility, and artistic excellence? We need a guide . . . and Giacomo Casanova, a representative par excellence of the moment, would be delighted to step in.

Why Casanova? He was sharply intelligent, an ambitious author and playwright, a financial opportunist, and a spy. A social climber by virtue of his wit, he was able to fit in just about anywhere and eager to make connections with those who could further his desires. He went everywhere, knew everyone, and wrote it all down. His twelve-volume autobiography—The Story of My Life—provides an unrivaled account of 18th-century society as well as his personal exploits. As we follow in Casanova’s footsteps from his native Venice to some of the great cities of Europe, we tread a path through this era’s life and culture that nobody else walked in quite the same way. There is no denying, however, that he is also a problematic anti-hero – the very definition of a womanizer, con man, and a fraudster.

Masks are everywhere in this painting by the Venetian artist Francesco Guardi. In the complex social environment of 18th-century Venice, identity could be invented and performed by anyone, as an actor performs on the stage, and masks played a significant role. Fanciful masks were worn for balls and the magnificent carnival season that preceded Lent, but white half-masks were also worn daily for half the year, from October until Lent. They were a perfect way to circumvent Venice’s strict social hierarchy, enabling interaction between people of different classes. And they offered anonymity, allowing lower-class citizens—so long as they were suitably dressed—to mingle with the wealthy at the public gambling hall or the theater, to become “equal” for a few hours, at least.

The interiors of Venetian palaces, or palazzi, were richly appointed with elaborately carved furnishings, delicate gilded stucco plasterwork, sumptuous damask walls, frescoed ceilings, and paintings by the masters of the day. In addition to grand ballrooms, Venetian palazzi also contained smaller, intimate spaces, still richly decorated but specifically designed for more private encounters, such as courtship. In this painting by Venetian artist Pietro Longhi, set in closer quarters, there’s more going on than a simple music lesson. Music itself, involving harmony and emotion, often symbolized love or romance. And the pianist certainly seems more interested in the young woman than in his keyboard. Similar paintings by Longhi hang in the small but regal interior of the Ca’Rezzonico, shown below.

Casanova’s memoirs are filled with accounts of his experiences in such lush environments which he enjoyed both in Venice and later in Naples and Rome. Constantinople, now Istanbul, was the first of Casanova’s many journeys abroad, which would add up to 40,000 miles over his lifetime—an extraordinary achievement at a time when travel was difficult, dangerous, expensive, and time-consuming. Even just the 140 miles between Rome and Naples took six days by coach.

This was the era of the libertine, a freethinker who rejected polite society’s conventions regarding love and sex. Libertines challenged the constraints of marriage and the condemnation of adultery. More broadly, the 18th century was a period in which notions of personal liberty expanded, ushering in new thinking about both sexual promiscuity and the ideal of romantic love. Within this environment women at times found more freedom, but they also ran greater risks. Bearing children during this period remained dangerous, with 1 out of 10 women dying during childbirth. For women in society, a baby born out of wedlock meant scandal for her family. For a female servant, it could spell complete ruin.

Before the 18th century, mythological images of the gods displayed heroic conquest and were restrained in their nudity. But by the time of Casanova, themes of love proliferated. In this French painting of 1770, Venus, the goddess of love, and her paramour, Mars, god of war, appear as naked mortals, in a bed rumpled by the night’s activities. The language of mythology gave many artists license to explore overtly erotic themes that reflected the era’s permissive attitudes toward sex. But not everyone was persuaded; the French philosopher and critic Denis Diderot deplored such displays of flesh, writing that he was tired of so many images of “tits and asses.” Symbols associated with classical mythology provide a veneer of respectability to this racy scene. Doves build a nest in Mars’s armor, signaling the peace brought about by the sensual reconciliation between the deities of love and war.

Manon Balletti, painted here at age 17, was the daughter of Silvia and Mario Balletti, the theatrical family who befriended Casanova when he first arrived in Paris. After having an affair with Silvia, Casanova fell deeply in love with her daughter. His relationship with the younger Balletti was a tumultuous one, and their affair came to an unhappy resolution for Casanova: Manon eventually rejected him and married another.

Although Casanova was unable to retain the affections of Manon, his time in France proved financially successful. In an astonishingly audacious endeavor, he successfully pitched French officials on establishing the first national lottery—taking ownership of the idea after hearing it explained and using his own masterly powers of persuasion to make it happen. The lottery built Casanova’s reputation as a financial wizard, and endless credit was extended to him. He set up an expensive textile workshop, but squandered huge amounts of money on it. Eventually, the market collapsed and Casanova lost almost all of his fortune. Loveless and penniless, Casanova was forced to move yet again, this time to England.

By 1763, when Casanova began a nine-month visit to London, it was the biggest city in Europe. Its growing wealth was based on international trade, banking, and insurance. Casanova found British society very different from the Venetian and Parisian environments he had become adept at negotiating. In London, there was no glittering court, and his deficient English limited his opportunities. Nevertheless, the London chapters of his memoirs are crowded with accounts of places he went and people he met.

Londoners of all social classes went to Vauxhall Gardens for fireworks, music, and people-watching. In this print, well-dressed patrons stroll among the octagonal orchestra pavilion, Turkish dining tent, and supper boxes. Vauxhall was the place to see and be seen.

Kitty Fisher, London’s most celebrated courtesan, was one of the world’s first celebrities. Similar to reality television stars today, Kitty was an astute businesswoman and famous simply for being famous, illustrating the emerging influence of mass media on public opinion. Artists frequently reproduced portraits of beautiful women in prints and spread their images near and far, multiplying their fame. In this portrait Kitty is shown in a grand setting, with fine clothing and jewelry earned by her profession. The painter plays on her name with the little kitten fishing in the glass bowl. Naturally, an assignation with London’s foremost courtesan was irresistible to Casanova. Yet nothing sparked between the two. Casanova’s English was not up to the witty banter he liked to employ with women, and, as he put it, “love without language is an ugly business.” His lack of English marred his enjoyment of London, and shady financial dealings eventually forced him to flee back to France to avoid arrest.

Casanova’s biography abruptly ends in 1774, when the more adventurous chapters of his life had passed. In 1785, at age 60, he became librarian to Count Josef Karl von Waldstein at Duchcov Castle, Bohemia (now the Czech Republic). Casanova complained of the lack of excitement in letters to friends, but his years there were productive. He completed Icosameron, a sprawling science-fiction novel that did not bring him the anticipated fame and livelihood he had hoped for. Turning to his own sensational recollections, he wrote The Story of My Life. “Writing my memoirs was the only remedy I found to avoid going mad or dying of grief,” he wrote in a grim aside to his usually sunny narrative. Casanova remained at Duchcov until his death, in 1798, at age 73.