(work in progress)
Well, actually it's all three ...
One of the charms or challenges of travelling in South Africa (depending on your perspective) is that we are a country that has more than one official language. In fact, since the transition to democracy in 1994, we actually have 11 - which is a bit too inclusive to be practical in my opinion - and even in the Bad Old Days of pre-democracy, both Afrikaans and English were recognised as dual official languages.
But, back to Simon's Town/Simons Town/Simonstown. In English, the correct spelling is 'Simon's Town' as it was named because it was located on Simon's Bay (now False Bay) which was named in honour of the early Cape Colony governor, Simon van der Stel. However, this has often been corrupted to 'Simons Town' or 'Simonstown', particularly by non English speakers, who find the English use of the apostrophe confusing. This isn't unexpected, as many native English speakers have trouble using this pesky little piece of punctuation correctly, and to add to the confusion, in Afrikaans, the apostophe is sometimes used to indicate a plural (for example, the Afrikaans plural of 'taxi' is 'taxi's').
Oh, and just to add further confusion, in Afrikaans, it's known as 'Simonstad' ...
So, other than being a piece of cultural whimsy, why should this be relevant to you? Well, the differing spelling of the name for the same place can cause problems when looking for information: an excellent example of this would be the VT website itself, which only recognises the 'Simon's Town' spelling. So if you're searching for a particular place name (particularly one which contains an apostrophe), then be sure to check the other possible permutations.
All South Africans accept that Cape Town is a different world ... it's not until we start reading their warning signs that we realise QUITE how different!!!
Capetonians are renowned - some would venture, 'notorious' - for their laid back manner, which makes us frenetic Johannesburgers want to give them a good shake to return them to reality. So whilst you're doing the responsible thing and checking for penguins with suicidal tendencies who may have parked off under your car, perhaps it would be also prudent to also check for those 'laid back to the point of being comatose' surfy types, who may have decided to commune with the penguins and have a nap under there too ...
(work in progress)
The Boulders may be a designated nature reserve, but that only restricts people entering penguin nresting areas, and doesn't prevent the little darlings going walkabout! Penguins have taken up residence most places in Seaforth (the suburb of Simon's Town that abuts Boulders Beach) and although they lie low during the day when there are people around, they are very much in evidence after dark.
These two were out jaywalking along the road linking Seaforth to the main road every evening we were there, and live in the adjacent stormwater drain. So if you're driving in this area after dark, be especially cautious and remember that they most certainly have right of way!
(work in progress)
Finding parking is always a challenge along the False Bay coastline - particularly in peak season - as the towns have developed as ribbons along the narrow coastal strip of flat land between the mountains and the sea. There is limited street parking along the main road in Simon's Town, but this fills up quickly, so you need to get there early to get a place.
It is therefore somewhat of a relief to know that there is a small public parking area on Jubilee Square, which has the added bonus of wonderful trees that lend excellent shade (also often in short supply along this coastline). The tariffs are reasonable, so I would therefore suggest that you try to park your car here when you arrive, and use this as your base to explore not only the harbour but the gorgeous architecture of the Historic Mile and Simon's Town's delightful backstreets, as well as the unexpected Simon's Town mosque, which is located up a flight of stairs in a narrow alley on the other side of the main road.