Tavern on the Bay is a privately owned business in a Victorian home overlooking the bayfront of historic downtown Saint Augustine. Here you have a panoramic view of the fort, Matanzas Inlet, horse and carriages & the Bridge of Lions. The private rooms have a very beautiful Victorian setting.

The tavern was once the private home of WIlliam Diskmuits, built in 1917. Mr. Diskmuits was the first president of Florida National Bank.

The site where Tavern on the Bay sits was well north of the original settlement of Saint Augustine, which was originally south of the Bridge of Lions. During the building of the Castillo, this location was probably an open house area used for construction storage or kilns for the making of tabby, a cement mixture of lime and crushed oyster shells. In 1668, pirates landed a few yards away, along the riverfront, and sacked the original St. Augustine settlement. In 1740, the area where you are sitting was in turmoil, as residents rushed to seek refuge inside the fort from the invading British. The redcoats landed and immediately places the Castillo de San Marcos under a siege that lasted a starving 38 days. During the Civil War, this area was occupied first by Confederates and secondly by Union troops. In the years following the Civil War, maps indicate there were a couple of Flimsy clapboard structures on this site which were most likely barns or single room dwellings. In 1887, most of this part of the city was destroyed when a great fire swept the area southward from this location to the Market Plaza. In the 1890's the Bennett Hotel was built at this location and remained in operation until the 1950's.

Robert "Bob" Henry was teh head waiter during the mid-1900's and would ride a bicycle to work each day from the city's Black neighborhood of Lincolnville. In the later years, city officials held meetings and socials on this spot, but did not ride their bicycles to the gatherings. Next to this location, at 24 Avenida Menendez was a waterfront house, now a bed and breakfast, which had a widow's walk on the roof. It was run by a lady who rented rooms to revenue agents during Prohibition. The agents were puzzled at why they were so unsuccessful at seizing rum-running boats that came regularly into St. Augustine harbor. It seems their landlady would signal the bootleggers offshore by hanging a lantern from the widow's walk can still see a lantern swinging from the top of the building at night. When Warner Brothers filmed "Distant Drums," a 1950's movie about the Seminole War, the movie executives made their headquarters at the Bennett Hotel. Gary Cooper, the star of the movie was lodged on this site during filming. On         , 200        and         held their historic wedding reception at this location, however, the British did not invade, and the pirates, being drunk at the time, did now sack the place.