This October, noted gay historian Andrew Lear of Oscar Wilde Tours will guide a new, immersive journey through Italy’s gay history and same-sex artistic heritage: Gay Italy: From Caesar to Michelangelo and Beyond. Running Oct. 9–18, the expedition begins in Rome, where participants will uncover the private lives of emperors, explore Caravaggio’s influential works, and visit locations celebrated in famous operas such as Tosca. The itinerary then moves to Naples to view the provocative displays of the Gabinetto Segreto, the historic “secret museum” gallery at the Naples National Archaeological Museum.
From Naples the tour travels along the spectacular Amalfi Coast and to the island of Capri before continuing south to the ancient Greek site of Paestum. There, well-preserved Greek temples and striking wall paintings with homoerotic themes reveal another facet of classical life. The route concludes in Florence, offering time to appreciate the city’s unparalleled Renaissance collections and the artistic achievements that shaped European culture.
Accommodations throughout the trip are selected for their beauty and distinct character, providing a comfortable and memorable base in each destination. Dining emphasizes authentic regional cuisine and fine local wines from three of Italy’s celebrated culinary areas. Highlights include tasting pizza Margherita in the restaurant where it was first created, sampling artisanal gelato, enjoying fresh buffalo mozzarella, and savoring babà al limoncello, the classic rum-soaked cake infused with lemon liqueur.
Groups are intentionally small to encourage conversation and a close-knit atmosphere; the tour is limited to a maximum of 18 participants. Single travelers should note that a single supplement may apply. This carefully curated itinerary blends expert historical insight, world-class art, and authentic local experiences to offer a focused exploration of Italy’s LGBTQ+ cultural legacy.