A Guide to Building Your Perfect Cape Town Itinerary

by Trav | Oct 8, 2015 | Destinations

Our real picture from the helicopter ride.

So, you’re heading to Cape Town, eh?

Or maybe just dreaming about it?

Either way, you’ve made a great choice, because Cape Town is one of the coolest, most fun, and most beautiful cities in the world.

If you’re taking an 18 day trip to Cape Town and want to do EXACTLY what we did, well, we’ve provided our complete itinerary.

And I’m flattered.

But more likely, you’re going for less days…or more days…or want to do some of your own things.

So to help you build your own perfect Cape Town itinerary, we’ve done four things:

1. Broken down our itinerary day by day.
2. Given you advice on what to do if you’re going for a longer or shorter time.
3. Created an ordered list of “must dos”.
4. AND created a cheat sheet of the best places to eat, sleep, and things to do.

So have a look, run with the things you like, and ditch the others.

And enjoy Cape Town, one of my favorite cities in the world!

Our Itinerary

Day 1 – Downtown Cape Town

(arrived late previous night, stayed at Park Inn Foreshore using Club Carlson points)

• Had lunch at the Food Market at V&A Waterfront
• Took a 20-minute helicopter ride.
  • Definitely opt for 20 minutes vs. 15 as this allows you to go behind Table Mountain.
  • Also, negotiate!  We were able to get it down to $80 per person.  Plenty of options all right next to each other, so just go around and ask their best price.
• Sunset boat cruise.
  • Sunset cruise costs about 220 rands per person ($16).  Bring a jacket or sweatshirt because it’ll get cold when the sun goes down.
• Had dinner at Quay 4 on the waterfront.
  • Avoid at all costs, this place is awful.
• Slept at Park Inn Foreshore.

Day 2 – Downtown Cape Town

• Moved to the Radisson Blu Waterfront, using Club Carlson points to book.
  • Easy, free parking on the street.  Cool views of the stadium on one side and the water on the other.  Walking distance to V&A waterfront.
• Went to Truth Coffee’s flagship shop downtown for lunch.
  • Really interesting spot with Heather’s favorite coffee in Capetown and good food.  Highly recommended.
• Went to the Eastern Bazaar for dinner.
  • Cheap and pretty good.  Interesting enough to check out if you have time.
• Slept at Radisson Blu Waterfront.

Day 3 – Downtown Cape Town

• Rained all day, so we actually stayed in, for the most part, doing work and reading.
• Walked to Origin Coffee stand at the waterfront.
  • 2nd best coffee in Capetown, but by far the best hot chocolate.  Yum!
• Lunch at the Food Market at V&A Waterfront again.
  • Followed by ice cream at The Creamery!
• Went out for a drink at the Fireman’s Arms.
  • The oldest pub in Capetown (I love anything that is the “-est”)!
  • Good spot to hang out, no idea how the food is. I wouldn’t suggest walking there at night as I did though.
• Slept at Radisson Blu Waterfront.

Day 4 – Downtown Cape Town

• Spent morning sipping hot chocolate and coffee on the deck of Radisson Blu.
  • Walk out the pier (even if you aren’t staying there, maybe you can sneak in) for a great photo op of Table Mountain and the stadium.

Met up with Jacqueline from Adventure Capetown, who tailors day tours to your specific desires.  She took us to do all of the following:

• Went to Knead Bakery for pastries.
• Headed north and stopped at Milnerton Beach
  • Great views of Cape Town and a nice beach – but cold water!
• Ate lunch at Klein Roseboom, a gorgeous little winery with great food.
• Tasted wine at the Klein Roseboom tasting room.
• Headed to the Ostrich Farm.
  • I wouldn’t go out of my way to see this unless you love ostriches, but they do have the world’s smallest ostrich here (those “-est” again!)
• Headed to Bloubergstrand and Big Bay to watch windsurfers and eat dinner at Primi.
  • If you have a car, worth going here to windsurf or just check out a different part of Cape Town.
• Went back to Park Inn Foreshore to sleep, using points again.

Day 5 – Downtown Cape Town

• Went to Arnolds on Kloof Street for lunch.
  • Everyone says to go for breakfast, but we didn’t find out they had an all-day breakfast menu until AFTER we ate lunch.  Opt for breakfast.
• Walked up Kloof Street and found a great cafe called Beleza.
  • Incredible pastries and neat buildings.  Love this part of town – highly recommend you just wander around here.
• Went to Greenmarket Square and bought some gifts for people.
  • Bargain, bargain, bargain!  I always start at about 25% of what they say and can usually get it at 50% or less.
• Drove to Hout Bay.
  • Stunning drive through Camp Bay and down the coast
• Ate at Fish on the Rocks in Hout Bay.
  • Certainly not the best fish and chips like everyone claims – they were average at best – but a neat spot if you are passing through right on the water.
• Drove up Signal Hill for sunset.
• Slept at Park Inn Foreshore

Day 6 – Downtown Cape Town then Wine Country (Stellenbosch)

• Went to Truth Coffee downtown. 
  • Hot chocolate was just ok, not near as good as Origin, but Heather LOVES the coffee!
• Dropped one rental car off at the airport, picked up another one (don’t ask).
• Drove to Vredenburg Manor in Stellenbosch/Somerset West to stay for a few nights.
  • Incredible place with amazing hosts, Leon and Luke.  We paid 1050 rand ($75) total for 3 people in one of their cottages and a fabulous breakfast was included.
  • LOVE this place (keep reading, you’ll see).
• Went to Ken Forrester for first wine tasting.  
  • Nice people, just ok wine.  But, they told us to go to…
• Annandale Farms for second wine tasting.
  • Our favorite winery of the whole trip.  An absolute must.
  • Incredible reds, super unpretentious, very “rustic”, and you can bring your own meat and bbq on their firepit if you want!
• Dinner at Vredenburg Manor.
  • 4-course meal on the patio prepared especially for us.  390 rand per person ($29).  Really fun and special.

Day 7 – Wine Country (Stellenbosch)

• Awesome breakfast (included) at Vredenburg Manor.
• Went to Delheim for our first wine tasting of the day.
  • They have wine and cupcake pairing (woohoo!) but you have to set it up beforehand (boo!) so I didn’t get to do it.  You should.  And tell me how it goes.
• Headed to Jordan for our second wine tasting of the day.
  • Prettiest winery we went to with decent wines.  Overpriced but pretty good food.
• Lovane Boutique winery was our third stop.  
  • The smallest winery on the wine route, so I had to go (-est!).  Neat downstairs tasting room.
• Walked around the quaint Stellenbosch downtown.  Worth stopping and doing, for sure.
• Watched South Africa vs Japan at a packed college bar.  
  • South Africa lost in the biggest upset in Rugby World Cup history (whoops!).
• Dinner at Col’Cacchio pizzeria in Stellenbosch.
  • Chain around South Africa but with good, reasonably priced pizza.  Not a bad option.

Day 8 – Wine Country (Stellenbosch)

• Awesome breakfast (included) at Vredenburg Manor again.
• Drove to Muizenberg, stopped to see the colorful beach huts.
• Went to Boulders Beach to see the penguins.
  • Easiest place in the world to see penguins, so you have to stop and see it.
• Ate lunch at Brass Bell in Kalk Bay.
  • Heard from a few people that this was THE place to eat in the area, but we were not impressed.
  • I’d recommend skipping it and trying Kalky’s (which we didn’t go to) instead.
• Drove to the Cape of Good Hope.
  • Arrived with only 2 hours before closing, which wasn’t enough time.  I’d recommend having at least 4 hours so you can explore more.
• Ate dinner at Thai Cafe in Stellenbosch.
  • They have khao soi, my favorite dish in the whole world, which was very surprising.  Unfortunately, it was just average, as was the rest of the food.  I wouldn’t go out of my way to eat here.

Day 9 – Wine Country (Stellenbosch)

• Awesome breakfast (included) at Vredenburg Manor...again.  
  • But this time, we got cinnamon pancakes with caramel banana sauce.  Ask for them…wow!
• Did our first real exercise of the trip by going for a run.
• Spent the day relaxing around Vredenburg and doing work.
• Dinner at the Thirsty Scarecrow.
  • Awesome pub outside of Stellenbosch with their own, delicious strawberry beer.

Day 10 – Wine Country then Start of Garden Route

• Awesome breakfast (included) at Vredenburg Manor…again
• Lunch at the Farmer’s Kitchen – which is connected to the Thirsty Scarecrow.
  • Wow, some of the best food we had the entire time.  A must go for brunch or lunch (only open until 5 pm).
• Started driving out the Garden Route to Plettenberg Bay.
• Stopped in Hermanus.
  • Great spot for whale watching – saw one as soon as we pulled up.
  • Wandered around the cute downtown area, bought a book at Hemmingway’s bookstore, which is a neat spot.
• Drove to Arniston and stayed at “Marlene’s Fishing Cottage”.
  • Booked for us by Leon at Vredenburg Manor House.
  • This is a very barebones house with 2 bedrooms.  I wouldn’t recommend it unless you want a real rustic, out of the way spot.
• Ate dinner at the restaurant/house next door, Willene’s.
  • Worst food we had the whole trip – if you somehow find yourself in Arniston (and why would you?) – avoid.

Day 11 – Garden Route

• Woke up for sunrise over Arniston, the one plus.  
  • Then got chased by wild dogs, so even that got ruined.
• Drove to Mossel Bay.
  • no real reason to stop here.  Keep pushing on to somewhere better.
• Lunch at Salinas in Wilderness, which was recommended by Leon from Vredenburg.
  • Great call Leon!  Spectacular views over Wilderness beach and really good food.
  • Ask for the half grilled, half calamari platter (not on the menu, I made it up).  It’s awesome, as are fish and chips.
• Stopped and wandered around Knysna.
  • Cool town, much better place to stop and explore than Mossel Bay.
• Drove to Plettenberg Bay.
• Ate dinner at The Table in Plettenberg Bay.
  • Great salads and pizzas and a fun place to sit outdoors.
• Slept at Robberg Beach Club.

Day 12 – Garden Route

• Ate breakfast at Robberg Beach Club (included)
• Hiked the 5-hour Robberg trail.
  • One of the best things we did on the entire trip.  Incredible cliffside hike where you’ll see seals, whales, and maybe even sharks.
• Ate dinner at Fat Fish.
  • After 5 hours of hiking, anything would have tasted good, but this was an awesome meal.  Definitely eat here – but call for reservations, they get busy.
• Slept at Robberg Beach Club.

Day 13 – Garden Route then back to Downtown Cape Town

• Ate breakfast at Robberg Beach Club (included).
• Hung out on the beach for three hours.  
  • Went swimming, water was cold refreshing!
• Ate lunch at Salinas in Wilderness – again.
• Got 3 speeding tickets driving the Garden Route back to Cape Town (do as I say, not as I do!)
• Booked an apartment on AirBnB for the next four-night, arrived in Cape Town at 10 pm and went to bed.

Day 14 – Downtown Cape Town

• Went to the incredible Saturday market at the Old Biscuit Mill.  
  • If you’re here on a Saturday, this is a must for the food alone.
• Drove to Klein Constantia winery set in a beautiful area south of Cape Town.
• Ate late lunch/dessert at Jonkershuis Restaurant at Groot Constantia winery.  
  • Jacqueline’s favorite “upscale” restaurant in Cape Town and a real gem.
• Went to The Devil’s Peak Taproom to watch South Africa in the Rugby World Cup…
  • …and sip on the best craft beer and cider in Cape Town.
  • Definitely head here for good food and drinks.
• Ate dinner at Sawadee Thai restaurant in The Gardens neighborhood of Cape Town.  
  • Decent food at good prices.

Day 15 – Downtown Cape Town

• Drove to Hout’s Bay for the weekend market (open Friday, Saturday, Sunday).
  • If you miss the market at the Old Biscuit Mill or you just love markets (like us), this is worth the drive.
• Went shopping at the Canal Walk Mall
  • Not exactly my idea – but still cool because it’s 3rd biggest mall in Africa.
• Heather and her sister went to see a movie at the waterfront.
• I ate dinner at Hudson’s Burger Joint (just ok) while trying to (unsuccessfully) stream NFL games on my laptop – a big night out!

Day 16 – Downtown Cape Town

• Hiked up Table Mountain via the Platteklip Gorge route.
  • Started at 10:00 am, reached the top at 12:30 pm.
  • Awesome hike but a bit difficult.  Wear good shoes and bring plenty of water and sunblock.
  • We “treated” ourselves and took the cable car down, which is what many people do.
  • Overall, this is a definite must-do in Cape Town.  Fantastic views!
• Ate lunch at Addis in Cape.
  • Fun, friendly Ethiopian restaurant with a good, filling lunch special (99 rands).
• Drove to and wandered around Kirstenbosch Gardens.
  • Neat botanical gardens right at the foot of Table Mountain so you have great views (of what you may be just climbed!).
  • Worth the visit even if you aren’t a “flower person” like me.
• Ate dinner at Beluga.
  • Known as one of Cape Town’s best restaurants – rumor has it that Prince Harry dined here – it’s got good food at reasonable prices.
  • We opted for the “set menu”, where three courses are 190 rands and you can pick from a variety of options.  Great value and nice ambiance.

Day 17 – Downtown Cape Town then back to Wine Country

• I started my day by getting a shave and haircut at Yogi’s barbershop.
  • Awesome, old school barbershop in heart of Cape Town that’s an experience in and of itself.
  • Highly recommended for guys who want a trim – haircut and straight razor shave cost less than 200 rands ($15).
• Went back to V&A waterfront for early lunch and to shoot some videos.
• Camera battery died, so went back to Devil’s Peak Taproom to record a podcast while tasting beers and charging batteries.
  • Multi-tasking never tasted so good!
• Back to the Old Biscuit Mill – close to the Devil’s Peak Taproom – for more filming.
• Went shopping at Green Market Square to pick up last-minute gifts.
• Headed to the Beerhouse on Long Street for more “filming”.
  • Where I had to – in the name of research – sample 3 more beers!
• Back to Devil’s Peak – yes, this is twice in three hours – for dinner.
  • Tuesdays have live music and a crazy burger and beer special for 65 rands.  Couple that with rugby on tv and I was in heaven.
• Drove back to Vredenburg Manor in Stellenbosch/Somerset West.
  • We loved this BnB so much we went back for our last night and so we could have a great breakfast in the morning.
• Went out to Thirsty Scarecrow to meet up with EPoP reader Bryan Teare.

Day 18 – Wine Country (Stellenbosch)

• Awesome breakfast (included) at Vredenburg Manor…for the last time.
• Drove to Cape Town airport.
  • One thing that is great about Cape Town airport is that it’s so easy to get to from both downtown and the wine region – 30 minutes max on the highway.
• Shot intro/outro videos in the airport.
• Got on the plane and headed off to New York via Abu Dhabi.
  • Cried because we were leaving the amazing city of Cape Town.

So there you have our exact itinerary for 18 days in the Cape Town area.  But here are our suggestions for people with more or less time in Cape Town.

If You Have More Time in Cape Town:

• Hit up Cape Town attractions we missed such as Robben Island, District Six Museum, and Castle of Good Hope.
• If you’re adventurous, dive with great white sharks (I’m definitely doing this when I come back).
• Spend a night or two at towns along the Garden Route.  I’d recommend Hermanus and Knysna.
• Check out even more wineries around Cape Town by heading to Franschoek or Paarl (or both!).

If You Have Less Time in Cape Town:

• Out of the three regions – Cape Town, wine country, and the Garden Route – I’d cut out the Garden Route.
  • The drive is boring and far (and you may end up with speeding tickets!) and you can get the same feel by going to coastal towns much closer like Hout Bay.
• Pick up the pace.
  • We did things slower because we had more time and had to film stuff.  Cape Town is easily navigable, so you can fit a lot of the stuff we did in downtown Cape Town in a few days.
• Take a day tour out to wine country.
  • If you’re really pressed for time, you can do a wine tour in one day (like EPoP reader Nate). We loved staying out there and spending time in Stellenbosch, but a day tour will allow you to at least see it.

And since I have no idea how many days you have or your travel style, here is an ordered list of what I think are the things you can’t miss in Cape Town.

It always helps to know the “best of the best”.

Things I Wouldn’t Miss (starting with the most important)

• Hiking Table Mountain – if hiking is too hard, you can take the cable car up and down.
• Cape of Good Hope – stop to see the penguins at Boulders Beach!
• A trip to wine country – whether that be one day or a week, get out there.  And if you’re in Stellenbosch, go to Annandale, our favorite winery.
• Old Biscuit Mill Saturday market.
• Helicopter ride over Cape Town.
• V&A waterfront – wander around, take a boat cruise, eat at the market.
• Truth Coffee in District Six for coffee lovers and Devil’s Peak Taproom for beer lovers.
• Drive-up Signal Hill.
• Drive out to Milnerton/Big Bay for views of Cape Town.
• If you do drive the Garden Route, hike Robberg Trail in Plettenberg Bay.

Have you been to Cape Town?  If so, what are some of your favorite recommendations?  What did you love?