- Main Road - The Main Road running through Simon's Town changes its name at regular intervals from Main Road to Station Road, St George's Street. Queens Road, Macfarlane Road and then back to Main Road
- Admiralty House off Station Road was originally the home of the naval commandeer and is now open to the public. Built in typical Cape Regency style by VOC Antoni Visser in the early 19th century.
- Church of St Francis on Court Road which was built circa 1837 and is rumoured to be the oldest Anglican church in South Africa.
- The Residency on Court Road houses the Simon's Town Museum. The building has also served as the offices of the magistrat and the governor's retreat, hospital, slave quarters and prison.
- Jubilee Square is the heart of Simon's Town and home to a myriad of shops, market stalls, pubs, coffee shops and street vendors. Jubilee Square is also home to the bronze statue of "Able Seaman Just Nuisance", the only dog ever to be enlisted in the Royal Navy.
- False Bay Yacht Club lies north of Jubilee Square offering first class moorings, fishing boats, yachts and kayaks for charter from the centre.
- Warrior Toy Museum on St George's Street always popular with the kids holds a collection of antique and more recent children's toys including old dolls, trains and original lead soldiers which date back to the 1700s.
- Roman Rock Lighthouse situated at the harbour entrance was built in 1861 to guide the ships visiting Simon's Town into the precarious bay. Roman Rock Light House is still in full working order and is said to be the third oldest lighthouse in South Africa.
- Martello Tower and the Naval Museum document South Africa's rich maritime history.
- Boulders Beach also known as "The Boulders" is home to one of the largest colonies of endangered African penguins. The beach is protected by massive granite boulders which create this safe protective enclave for the penguins.
- Beaches: visit Boulders, Foxy, Seaforth, Long and Glencairn.
- Miller's Point is popular especially during spring when Southern Right, Humpback and Bryde's Whales visit the point. Miller's Point is where you'll find one of South Africa's most highly acclaimed seafood restaurants the Black Marlin, definitely worth a visit.
- Smitswinkelbaai forms part of the Cape of Good Hope Nature Reserve and is inaccessable by car. Stunning beach ideal for swimming and fishing, the walk down the steep footpath is really worth it.
Simon's Town was originally named Isselsteijn Bay from a Dutch East Indiaman of the same name who sheltered there in 1671 during a storm. Reports from this ships' crew filtered back to the Governor of the Cape, Simon van der Stel that the bay provided ideal shelter from the winter winds and storms of Table Bay. This prompted Van der Stel to explore the bay, duly recommending the development of the bay which was later renamed Simon's Bay in his honour.
The British converted Simon's Town to a naval base in 1814 for the South Atlantic Squadron. Workshops were erected in addition to the barracks and forts which were built in 1743 and continued to operate until the South African Navy took over the naval base on 02 April 1957.