Cape Town South Africa Itinerary

Cape Town is that rare diamond of a travel destination that actually lives up to its hype. It has PENGUINS just CHILLIN on a beach for goodness sake! If you don’t love that, then you also must hate puppies and candy, and might need a hug. Cape Town is fully satisfying in it’s beauty, diversity, and itinerary, which for any traveler is just about the best thing ever.

Here’s my favorite way to spend 3 days in Cape Town:

Day 1:

  • Wake up at the Cape View Clifton luxury boutique hotel to an amazing water view in Clifton.
  • Having booked a private driver, you’ll set out at 9am for a tour of the beautiful Peninsula.
  • First stop is Muizenberg to take pictures of those famed colored beach houses. Warning, those are actual changing rooms so knock before you open one or be greeted by a naked South African screaming “close the door bru!”
  • On to Kalk Bay where you pop into great art galleries. Make sure to check out the art of Anat Oren at Chameleon gallery, her work is a personal favorite.
  • From the Kalk Bay strip you can walk right to your lunch at Harbour House, which you’ll have pre-booked a window table for 12:30pm to eat their deliciously fresh daily specials and feel skinny while watching the plump seals sunbathe on the rocks beneath you.
3 days in Cape Town Penguin Beach
  • Then by 2pm it’s PENGUIN TIME! Walk the long wooden platform at Boulder’s Beach to end up in the most adorable beach in existence. Make sure to check beneath your car for penguins before leaving, they may try to hitch a ride back to Antarctica with you!
  • Settle into a post penguin nap while driving the hour down to Cape Point and Cape of Good Hope to see where the Atlantic and Indian oceans meet. Keep an eye out for baboons and ostriches that are sightseeing as well (you thought we were the only mammals who like to vacation?!)
  • Enjoy a sunset drive around Chapman’s Peak as you make your way back north for dinner. The roads are a bit windy, but the views are pretty spectacular.
  • End the long drive at an 8pm Kitima reservation, where you’ll dine in a 17th century Cape-Dutch homestead.
  • With a second wind you finish with some drinking on Long Street.

Day 2:

  • At 9am, with the same private driver, you’ll embark on everyone’s favorite day of the week…winery day!
  • 45min of driving puts you in the wine lands at the perfect time for your pre-booked 10am tour of Babylonstoren’s “Garden of Eden”.
  • By 11:30am you’re off to your 12pm lunch reservation at Delaire Graff, where you’ll dine on the terrace and take in the best views in Stellenbosch. Warning, excessive drinking could cause purchasing of South African diamonds in their shop…a girl can dream right?!
  • You turn into a South African pumpkin by 1:30pm and it’s time to roll to Grande Provence Wine Estate where you’ll taste wine (obviously), check out their art gallery and peruse their boutique of local crafts.
  • As if the day wasn’t already going swimmingly, your next stop is a wine and chocolate paired tasting at Lanzerac, the home of the first Pinotage. (tip: their chocolate tasting is technically paired with their middle range wines, ask them nicely if you can do a tasting of their higher end heritage wines instead and match the chocolate best they can to those wines)
  • Stumble your way (that private driver is coming in handy right about now) to Meerlust, who tout themselves as the oldest winery and have some of the best wines in South Africa.
  • End your day at Waterkloof for sundowners and a 7pm dinner reservation with a beautiful view.
  • Now I dare you to stay awake on the car ride back to the hotel!

Day 3:

  • Day 3 can start one of two ways: you could wake up at 6am and sweat out the hangover by hiking 2hrs up Table Mountain, or you could leisurely wake up, buy your cable car tickets online to skip the line like a pro, and take the entertaining glass bubble up the mountain at 9am. Either way you’ll get to experience one of the 7 natural wonders of the world (tip: the cable car closes if it’s too windy, rainy, or cloudy, so check online to make sure it’s open when you want to go).
  • After taking in the panoramic views of Table Mountain, head to the world’s first indigenous botanic garden, Kirstenbosch National Botanical Gardens. Assuming you’re not afraid of heights, check out their tree canopy walkway, it’s worth the hike.
  • Famished from your hike, cable car, and garden filled morning, you sit down for your 1pm reservation at La Colombe in Constantia.
  • Refueled and ready to spend some South African rand you head to The Watershed at the V&A Waterfront. The Watershed has awesome locally made items that are well worth the schlep home. Afterwards walk through the V&A Food Market for some tasty treats and stroll around the V&A Waterfront promenade.
  • Sundowners are then consumed at Camps Bay taking in the beach views while scheming an outlandish, but plausible, plan to leave your normal life behind and shack up in a multimillion dollar home on the hill above (see day 2 for explanation on how you woke up owning said home and not remembering how it happened).
Best Boutique Hotels Cape Town, South Africa Cape View Clifton
  • Ready for more amazing food, you’ll head to The Old Biscuit Mill in Woodstock where you’ll sit down at one of two amazing restaurants for your 8:30pm reservation. Pot Luck Club is more casual and trendy with small plates (by this I mean tapas style, not like the plates are physically tiny in size…these plates need to be at least…10 times this size!). Or there’s Test Kitchen, which is PLC’s fancier older sister that ranked 28th in the world last year. Either one you choose will require reservations up to 3 months in advance during peak season.
  • After dinner you end your night on trendy Bree Street or Kloof Street.

Now THAT’S how you see Cape Town in 3 days! Is there more to see and do in Cape Town? ABSOLUTELY. But, if you only have 3 days, you’ll have spent them wisely with this itinerary. For people who can spend more time, I’ll post a separate laundry list of additional wineries, hotels, restaurants, and activities.

Email if you want the contact information for our personal driver in Cape Town 🙂

Why not?!