Calle Vallaresso (Hotel Monaco & Grand Canal), Venice

Calle Vallaresso sits just off Saint Mark's Square, and for centuries it operated as Venice’s unofficial casino row. Gambling houses multiplied here with remarkable efficiency, and Giacomo Casanova was a regular presence. For a man with expensive tastes and unreliable income, cards offered a quick fix—along with a steady supply of conversation, flirtation, and fresh acquaintances. Winning was helpful; being seen was essential.

Casanova’s preferred arena for high-stakes play—and high-stakes seduction—was the building that now houses the Hotel Monaco & Grand Canal. In the eighteenth century, this was Il Ridotto, Venice’s most famous gambling establishment. Behind gilded leather walls and under glittering decoration, nobles and non-nobles alike gathered at the tables, provided they wore a mask—the baùta—being the great social equalizer. Rank stayed outside; luck and nerve took over.

Officially, games here were fair. Unofficially, the house had learned a few elegant tricks. Over time, Il Ridotto and its competitors refined discreet methods to tilt the odds, separating eager players from their money with impressive consistency. Casanova, sharp though he was, fell victim more than once, recording both his losses and his bruised pride.

Ironically, the lesson stuck. At one point, Casanova found himself running a small gambling operation of his own, backed by a wealthy patron. In Venice, after all, experience—even the expensive kind—was never wasted...