Our History

Ever wondered why it is called Longboat Key?

Juan Anasco, scout and treasurer, first explored this area under orders to find a suitable landing place for Don Hernando De Soto’s party. Anasco told his leader that the only way to get through the pass from the Gulf to the Bay was by longboat, hence one explanation for the name Longboat Key.

Can you remember the first time you stepped foot on this property?

Anasco is said to have been the first man to set foot on Longboat Key and the present location of The Diplomat (3155 Gulf of Mexico Drive) is said to be the location.

What was built here before The Diplomat?

The popular resort, The Cheeri-Ho Beach Cottages, advertised as distinctive simplicity, aerated water, and charm in a tropical setting. However, it burnt down and is now the location of The Diplomat.

What was it before it became The Diplomat Beach Resort?

During World War II, it was reported that German submarines were in the Gulf of Mexico. The U.S. Coast Guard took over the Cabana Club (now The Diplomat) staffing it with men and dogs, so that the beach might be patrolled at night looking for “aliens.”