This is doable. Depending on what area you mean when you say wine land and how many wineries you'd be interested in visiting. It also depends on where you're staying. You could literally be staying on a wine estate in Constantia and, well, you don't have to drive far to get to the winery and all you'd really need is a guide/driver to other area wineries and out to Boulders (for the penguins).

Where are you staying. Can the hotel assist? How comfortable are you with driving yourselves around CPT.

Again, I'd ask the question about how comfortable you are driving yourselves. And, do you really need a "tour guide" or a hotel-arranged driver from place to place.


Folks here in this forum will generally ask you for a few more details about yourself and your trip details (time of year visiting, length and place of stay) and your travel habits, needs, level of comfort, etc. Cape Town can be everything from backpacking and hostels to ultra luxury and concierges and staff at your disposal with a myriad of prices and options in between.