Picturesque Simon's Town has many lovely old buildings and possibly the peninsula's best swimming beaches at Seaforth and Boulders, a gem that is also home to a large colony of African penguins. The town has had a long association with the Royal Navy. British troops landed here in 1795 before defeating the Dutch at the Battle of Muizenberg, and the town served as a base for the Royal Navy from 1814 to 1957, when it was handed over to the South African navy. Today you are bound to see plenty of men and women decked out in crisp white uniforms.
Jubilee Square, a dockside plaza that serves as the de facto town center, is just off the main road (St. George's Road). Next to the dock wall stands a statue of Just Nuisance, a Great Dane adopted as a mascot by the Royal Navy during World War II. Just Nuisance apparently liked his pint of beer and would accompany sailors on the train into Cape Town. He had the endearing habit of leading drunken sailors—and only sailors—that he found in the city back to the station in time to catch the last train. The navy went so far as to induct him into the service as an able seaman attached to the HMS Afrikander. He died at the age of seven in April 1944 and was given a military funeral. Just below Jubilee Square is the popular Simon's Town Waterfront, with numerous shops and restaurants. Day cruises, deep-sea fishing trips, and kayaking trips leave from the harbor.
If you're looking for something to entertain children the area has quite a few child-friendly options, including the SAS Assegaai, the South African Naval Museum's submarine, which is moored in the harbor with former submariners as guides.