From August 1895 to October 1897, she and her father assumed the lives of itinerant aristocrats traveling across Europe and the British Isles. They stayed in the French Riviera, Paris, and on the island of Jersey, as well as England, and Scotland. Kaʻiulani was treated as royalty in the French Riviera where they wintered each year and made friends, including Nevinson William (Toby) de Courcy, a British aristocrat who corresponded with her over the next three years and saved her letters until his death.