Its original English name was Fifth Creek Island. Its first known white settler was Captain James Mackay, who served under General Oglethorpe at Fort Frederica. Subsequent holders included a series of St. Simons Island plantation owners, who used the land primarily for grazing. In 1926, automobile magnate Howard Coffin added it to his other land purchases in coastal Georgia. Two years later, on the advice of friends who foresaw the potential in oceanfront properties, he opened the Cloister Hotel that was nicknamed the "Little Friendly Hotel" and turned over its management to his cousin, Alfred W. Jones. Upon Howard Coffin's death in 1937, A. W. Jones inherited the property, along with other tracts of nearby coastal land owned by the Sea Island Company.From its beginnings, the Cloister was a success, attracting a variety of "Roaring Twenties" luminaries. When President Calvin Coolidge decided to spend his Christmas holidays on Sea Island in 1928, the new hotel gained national attention. Promoted as a quiet, worry-free escape, as opposed to some of the high-energy resorts in Florida, the Cloister appealed to businessmen, politicians, and celebrities, including New York Mayor Jimmy Walker, Edsel Ford, John D. Rockefeller Jr., Eddie Rickenbacker, and many others. In addition to the hotel, Mr. Coffin also dreamed of creating a residential community on the island and encouraged his guests to consider building "cottages" nearby. To that end, he brought in electricity, water and telephone service, and improved causeway access to both St. Simons and Sea Islands. Among those building homes was Eugene O’Neill, who wrote the play Ah, Wilderness! while there.
