An estate suitable for someone of their social standing

The stories and legends of Pleasure Island are vast, and though many of the buildings have changed from their original purposes at Walt Disney World, the Imagineers themselves repurposed these buildings from Merriweather Pleasure’s original intent for them. Well, that’s if you believe the tales told around the island. Pleasure Island may now be as deserted as it was the day Merriweather found the area, but a place with so much history can never be totally empty, and at least the homes of the Pleasures still stand. These are the stories of Portobello Yacht Club and Fulton’s Crab House (previously known as the Empress Lily), as presented by the Pleasure Island Historical Society.

PLEASURE FAMILY HOME
1918

When Isabella Pleasure finally became convinced that her husband was serious about abandoning Pittsburgh for the wilds of Orland, she grudgingly agreed to move -- PROVIDED her husband built her an estate suitable for someone of their social standing. Merriweather commissioned Howard “Gaucho” Jones to build her the house of her dreams, and on July 4, 1918, the Pleasure family happily moved in. In very short order, Mrs. Pleasure became the leading light of Orlando society, hosting hundreds of tea socials, garden parties, croquet tournaments, and semi-formal dances, including the prestigious “Ides of March Roman Gala”, which raised thousands for charity. She and Merriweather hosted many luminaries in their home, including Teddy Roosevelt, Louis Comfort Tiffany, Samuel F.B. Morse, Robert W. Service, G.B. Shaw, Billy Sunday, Adolph Ochs, and Carl Hubbel. Her soirees were lively affairs, filled with fine food and uninhibited conversation. As she often said to visitors, “If you don’t have something nice to say about someone, come sit next to me!” In 1937, Mr. and Mrs. Pleasure built a new and even larger home where they lived for just four years (now the Disney Grand Floridian Hotel).

EMPRESS LILLY
1885

Originally built as “The Cox-Sherohman Floating Arts Palace, The Most Majestic ShowBoat on the Might Mississippi”. Colonel Tom Sherohman, Sir Roger Cox, and Their Original Dixie FootLighters sang, danced, and over-acted more than 8700 times on this boat. Their most popular melodramas included “The Laughing Octoroon”, “Bertha, the Sewing Machine Girl”, and “The Blackguard!”. Officially retired on October 29, 1909, after carrying President William Howard Taft from Yazoo City to New Orleans for the First Lakes-to-the-Gulf Deep Waterways Dramaturical Convocation. Purchased by Merriweather Adam Pleasure in 1911, re-named that same year for his beloved Aunt Lilly (wife of Pleasure’s zany Uncle Walt), and docked just off his Island in 1912. The “Empress Lily” served as home/guest home/entertainment center for the Pleasures in their early years in Central Florida. Once their home was finally completed in 1918, the “Lilly” was used mainly as a social center and floating summer palace. Every summer, from 1919 to 1928, Merriweather and Isabella Pleasure would cast off from this spot and guide the “Lilly” through the lush, tree-lined waterways of Central Florida. With the catastrophic decline of the St. Johns Aquifer in 1928, the “Lilly” became much less mobile. In fact, the Island’s “Grand Dame” was permanently moored here from 1928-43, when Stewart Pleasure took up residence on the top deck. He held an unending series of riotous parties on the boat, and two of those parties (1943, and 1954) ended with the biblious young Pleasure crashing the “Lilly” into the bridge on the opposite side of the Island. This once proud “Jewel Of The Mississippi” lay abandoned with the Island in 1955. In 1971, the “Lilly” was finally restored to her original glory by the Walt Disney Company.