Driving around Cape Town

I would drive, you will have enough time to take it easy, and the scenery from Cape Town to Hermanus to Stellenbosch to Franschoek to Cape Town is very beautiful. Only with a car you will be flexible to stop where you want etc. There is no real alternative for the route you are looking at (besides taking the bus to Hermanus and another bus to Stellenbosch). Driving around this part of South Africa isnt challenging.

Even if you like wine, I would consider spending one night in Hermanus, its s very pleasant place. And take the scenic way along the coast to there.

There are plenty of beautiful wineries to discover, and the Wine Tram (which is actually more a bus) is a good way to get to some wine farms. My favourite place at the moment is Babylonstoren https://www.babylonstoren.com (ots not on the tram route). The setting is beautiful, there is a huge garden, the cellar, a very good restaurant (make a reservation if you want to eat there) and its a lovely place to spend half a day.

I second Nathalie's recommendation for Babylonstoren - great place. Also nearby is the Franschoek Motor Museum - though by the sounds of it - cars might not be your thing.

If you're going from Hermanus it makes more sense to stop in Franschoek first before going to Stellenbosch.

Thanks so very much for your replies, I would certainly be happy to go to one or two wineries by driving, but the majority I will use the tram/bus.
I do like museums, just not the best driver in the whole wide world, but I'm thinking if I were to rent a GPS I should be ok!
I could definitely shuffle my dates around so I'm doing it in reverse, and ,y last night is in Hermanus before driving to the airport? Do I need to do a whale watch trip do you think, or would shore sighting suffice?

Hermanus - Franschhoek - Stellenbosch would be the best route. Going from the airport to Hermanus, I would use the coastal route (past Betty's Bay, etc.).

Never done a whale watching trip (in fact I always seem to be in Hermanus at the wrong time for whales) but I'd wait until the last moment to book. Weather (besides the whales location) can play a big part in whether the trip is worth it.

When you talk about the tram, I assume you mean the Franschhoek one - though I think there is a company in Stellenbosch that offers a similar hop on hop off service.

Yes I was talking about the tram from Franschhoek, but am also thinking of doing a hop on hop off bus in Stellenbosch too, just to really get a good range.

New question, if I am seeing Hermanus, Stellenbosch and Franschhoek separately from my time in Cape Town, would I still comfortably fill 2 full days and nights, or would 1 suffice. I'm definitely a bit worried about feeling lonely/lost in a big city setting?

I did a whale watching trip in 2013, and even though I usually don't get sea sick, I got sea sick. Not the throw up kind, but really dizzy and unwell for two whole days. About 50% of the people on the boat threw up. So I now prefer seeing the whales from shore. They get really close, so it is a good option. If you decide to do a whale cruise, take a sea sickness pill.

Don't drive to the wineries, because then you won't be able to enjoy the wine. Just drive to Stellenbosch or Franschhoek and take the tram, or do a wine tour. And visit some of the excellent restaurants in Franschhoek.

Wheather permitting, I would take pills and get on a whale watching trip. Yes, the whales come very close to the shore and you can observe them from there, which is also a great experience. But on a boat you get even closer, and as they are curious, they might swim really close to the boat (or under it), which is a great experience. And yes, I got sea sick, and felt quite unwell for most of the rest of the day, but for me it was worth it.

In case you take the Metrorail to the False Bay (to further explore Simons Town), consider stopping in Kalk Bay for lunch. The pier of the small working harbour is a great place for whale watching. And if you want to splurge, have lunch at the Harbour House (book a table at the window), its almost like your sitting in the sea.

I didn't mean to discourage whale cruise, it was an amazing experience, and as nathalie2 says the whales comes really close to the boat. I just meant that if you're going to do it, don't be brave (or stupid)like I was and skip the sea sick pills.

Thanks so much all, I might be being very ambitious, but I must say I come from a sailing background and have never suffered from sea sickness. So I'll definitely look into the boat.

Does anyone have any recommendations for budget accommodation in Stellenbosch or Franschhoek. I'm too old and boring for hostels, but a nice cheap basic central guesthouse maybe?

And regarding Cape Town itself, one day or two?