Travel for two weeks through a tapestry of the Cape Town region's attractions with this trip plan. You'll start with Cape Town itself as your base for day trips into the Winelands and out to the Cape of Good Hope, then drive off through smaller cities and towns. Visit animal sanctuaries, ancient caves, national parks, and more before ending your trip with a classic safari.


  • Sample the vintages of the Winelands
  • Meet the penguin colony of Boulders Beach
  • Paddle through Table Bay on a sunrise kayak tour
  • Delve into the Cango Caves
  • Seek out the “big five” and their friends on safari

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Cape Town Cape Town
Day 2 Guided Bike Tour of the Winelands Franschhoek
Day 3 Guided Cape Peninsula Sidecar Tour Cape Town
Day 4 Guided Sea Kayak & Table Mountain Tour Cape Town
Day 5 Cape Town to Greyton Greyton
Day 6 Greyton to Oudtshoorn Oudtshoorn
Day 7 Explore Nature & Wildlife in Oudtshoorn Oudtshoorn
Day 8 Oudtshoorn to Knysna Knysna
Days 9-10 Free Day in Knysna Knysna
Day 11 Knysna to Eastern Cape Safari, Sunset Game Drive Eastern Cape Game Reserve
Days 12-13 Eastern Cape Safari Eastern Cape Game Reserve
Day 14 Depart Eastern Cape via Cape Town  

Detailed Itinerary

Day 1: Arrive in Cape Town

Cape Town with Table Mountain in the background
Cape Town with Table Mountain in the background

Welcome to South Africa! Arrive at Cape Town International Airport and transfer to your accommodation to unpack and unwind. After you settle in, spend the rest of your day exploring the city. 

Known as the 'Rainbow Nation,' Cape Town and South Africa have a long and complicated history involving a multitude of ethnic and cultural groups. The area's history starts with the indigenous Khoisan and Bantu people, who were the primary residents of the area until the Portuguese and Dutch arrived in South Africa, beginning a centuries-long occupation. 

These days, South Africa is home to a diverse population. Roughly 80% of South Africans are of Bantu ancestry from a variety of ethnic groups, each with a distinct language. The remainder of the community is made up primarily of European, Asian (Indian, Chinese, and others from the formerly enslaved and indentured population), and mixed-race (Cape Coloured) ancestry. 

After checking in to your accommodation, spend the afternoon relaxing, taking in the views, and exploring the town. In the evening, head to the Victoria and Alfred Waterfront. Shop for art and crafts at the expansive Watershed market, visit the Two Oceans Aquarium to explore underwater life, or enjoy a harbor cruise as you watch the sunset. Other options include the Diamond Museum, which explores the history of the diamond rush in South Africa, or a helicopter flight to see Cape Town's sights from the sky. 

For dinner,  choose from a variety of restaurant and bar options.

Day 2: Guided Bike Tour of the Winelands

So many views
So many views

Start your morning with a pickup from your accommodation for your full-day biking tour. Spend the day riding a mountain bike through the vineyards of the Franschhoek Valley, stopping along the way for wine tastings. End the tour with a picnic lunch in the shade of centuries-old oak trees at a wine estate. 

Although the biking distances are short (maximum 12 miles/ 20 km), there's always an option to ride along in the support vehicle if you need a break.

Return to Franschhoek afterward for a relaxing rest of the day. 

Day 3: Guided Cape Peninsula Sidecar Tour

Cape Point
Cape Point

Hit the road with your guide for a full-day sidecar adventure on this Cape Peninsula tour. The Cape Peninsula is a rocky peninsula that juts out into the Atlantic Ocean at the south-western extremity of the African continent. At the southern end of the peninsula are Cape Point and the Cape of Good Hope. On the northern end is Table Mountain, overlooking Cape Town. The Cape Peninsula has outstanding flora and fauna and is part of the UNESCO World Heritage Cape Floral Region. 

Head out from Cape Town early in the morning, passing Cape Town University and Constantia before heading for Ou Kaapse Weg in Noordhoek. Stop here for a coffee break and some photos, then head to the Cape Point Nature Reserve where you will visit the Cape of Good Hope and the lighthouse.

Afterward, head to Simons Town and visit the penguin colony before breaking for lunch at a local seafood restaurant along the water in the sleepy fishing town.

In the afternoon head to the scenic Boyes Drive above Muizenberg—famous for its surfing—then continue to the Constantia Winelands district. Pick from the many wineries to experience a South African wine tasting, then return to the city in time for dinner.

Day 4: Guided Sea Kayak & Table Mountain Tour

Looking down the cableway
Looking down the cableway

Start your morning off with a sunrise kayak on the Cape Town coast. Meet your guide at Moullie Point, then cruise on comfortable and stable kayaks as you keep watch for dolphins, sunfish, and whales. Depending on your ability level, enjoy a relaxed morning paddle or test your skill on the water as you cruise around looking for wildlife. 

In the afternoon, let your arms rest with a hop-on-hop-off tour aboard the distinctive, open-top bus. Start at the Cape Town City Center Terminal, then take the bus to Table Mountain. From the bus stop, continue to the summit on the rotating cable car for spectacular views of the city, mountains, and ocean. Once at the top, take in the scenery from the walking paths. Keep an eye out for the playful dassies sunbathing in the sun (surprisingly, the little creatures are actually the elephant's closest living relative). 

Take the cable car down the mountain, then return Cape Town in time for dinner at the Victoria & Alfred Waterfront, where you'll find a variety of fine dining restaurants and pubs with views of the ocean.

Plan your trip to South Africa
Chat with a local specialist who can help organize your trip.

Day 5: Cape Town to Greyton

Greyton streets
Greyton streets

Pick up your rental car (or opt for a hotel delivery), then hit the road for your two-hour morning drive to Greyton. The drive there takes you along the R406, a road that's only slightly more substantial than a farm track, through wheat and sheep fields. As you arrive in Greyton, pass into the shade of the massive oaks that line the avenues of this sleepy town. 

Spend the rest of your day exploring on your own time. 

  • Take a stroll through the historic village of Greyton to see preserved buildings like the Moravian church, cobbler's home, and 1860s mud-brick homes
  • Meet a donkey at the EARS Donkey Sanctuary, a working farm that's a haven for ex-working donkeys. Put a carrot in your pocket and spend some time with Pedro, Lena, Boesman, and Dobbin, as well as a handful of other donkeys at the farm
  • Enjoy a wine tasting at one of the three boutique wineries near Greyton
  • Shop for antiques in the many small shops and boutiques that dot the town
  • Rent a bike for a relaxed ride around town. For an old-fashioned flair, rent a vintage bike for a leisurely cruise. If you're in the mood for an adventure, opt for an exciting mountain bike ride in the area (guided bike tours are also available)
  • Go for a hike and enjoy the abundant plant life in the Greyton Nature Reserve, one of the largest reserves in the Western Cape
  • Indulge in sweet handmade Belgian chocolates at the town's chocolatier. Sample dark and milk chocolates in flavors like Frangelico, rose geranium, and maraschino cherry

Day 6: Greyton to Oudtshoorn

Along the road
Along the road

After a relaxing breakfast, hit the road for the four-hour drive east on the famous Route 62 towards Oudtshoorn. Modeled after America's Route 66, Route 62 brings its own unique South African flair and distinct local character. 

More than just dive bars, farms stalls, or small country towns, Route 62 is full of surprises. One of the highway's legendary attractions is Ronnie's Sex Shop, a roadside bar, and restaurant. Legend has it that in the 1970s, local farmer Ronald Price set about opening a roadside produce sign, complete with a proudly handpainted sign. Mischevious friends took it upon themselves to amend the sign, ultimately convincing Ronnie to scrap the farm stand idea and open a bar for highway travelers. 

Forty years later the bar's quirkiness doesn't end with the sign. Inside, the entire room is decorated with traveler's graffiti, donated neckties and bras, and a random assortment of other oddities. As well as a restaurant, Ronnie's offers overnight accommodation, a pool with landscape views, and good old-fashioned respite from the dusty road. 

Other notable attractions along the way include the Ladismith Cheese Factory and the Barrydale Heritage Garden

Arrive in the late afternoon, then enjoy a relaxing evening. 

Day 7: Explore Nature & Wildlife in Oudtshoorn

Feed the ostriches
Feed the ostriches

Spend the day exploring the region's nature and wildlife. As you drive along the highway you'll pass by countless ostrich-filled paddocks, colorful feather stalls, and show farms. Palatial sandstone homesteads dot the landscape, a throwback to a time when ostrich feathers were worth more than gold.   

A stop at the Cango Ostrich Show Farm offers a glimpse into the farming industry and gives you the chance to come face-to-beak with the world's biggest bird (and their adorable fluffy offspring). 

From here it's time to dive deep underground, into the spectacular limestone chambers of the Cango Caves. Opt for the casual Heritage Tour to check out the cave's stalactite and stalagmite formations, as well as remnants of Khoikhoi paintings. To test your agility and contortion skills choose the Adventure Tour, where a series of tight squeezes and wiggles lead through narrow limestone chimneys on an unforgettable adventure. 

If there's time later, head out for a game drive in the Buffelsdrift Private Game Reserve to catch glimpses of the area's resident wildlife. 

Round out your day with ostrich steaks or kebabs at one of Oudtshoorn's many eateries and experience the region's legendary hospitality for yourself. If you get the chance, make sure to try the Karoo lamb—it's delicious.

Day 8: Oudtshoorn to Knysna

Houses on Knysna Head
Houses on Knysna Head

Start the morning with a drive to Knysna on the coast, approximately a two-hour drive from Oudtshoorn. The town of Knysna sits on South Africa's Garden Route and is a popular stopping point for travelers driving along the coast. It's located on the country's only national lake (which is also South Africa's largest permanent estuary).  

The town is a haven for outdoor adventure enthusiasts, foodies, and travelers seeking a quiet and relaxing getaway. After checking in, spend your afternoon enjoying some of the many activities the area has to offer. Go golfing on one of Knysna's three championship golf courses, shop for art and gifts in town, and visit the town's several heritage and cultural museums. 

Among other things, the Knysna Lagoon is world-famous for its oyster farming. Round out your evening with a decadent oyster dinner, then find the perfect place for a sundowner as you watch the sun sink below the watery horizon.

Days 9-10: Free Day in Knysna

Look for the Knysna's turaco
Look for the Knysna's turaco

Beautiful landscapes and adrenaline-filled adventures go hand-in-hand today. Start your day with a relaxing stroll on the beach in Knysna.

Continue east along the coast to Bloukran's Bridge where daring travelers leap into the gorge on the world's highest commercial bridge bungee jump. The bridge itself is relatively unassuming, but it's evident from the squeals and screams that this isn't an average photo stop. If you're feeling adventurous, try the 708 ft (216 m) jump and experience the thrill for yourself. If you would rather keep your feet on solid ground, head to the thick forests of nearby Tsitsikamma National Park for a beautiful hike. 

There's plenty of options to experience the region's beautiful nature. Enjoy a boat cruise on the Knysna Lagoon, take a guided walk in the Featherbed Nature Reserve, head upstream on a boat cruise of the Keurbooms River, or rent a paddleboard for a relaxed afternoon on the water. 

Visit Monkeyland, located in nearby Plettenberg Bay, to experience the world's first free-roaming multi-species primate sanctuary. 

End your day with a peaceful walk along the beach as you watch the sunset. 

Day 11: Knysna to Eastern Cape Safari, Sunset Game Drive

Grazing hartebeests
Grazing hartebeests

In the morning, hit the road for the 4.5-hour drive to a private game reserve on the Eastern Cape. After arriving, head out for your first evening game drive. Take in the sunset views while enjoying drinks and snacks like biltong—a South African favorite. 

Spend your time at the reserve enjoying daily morning and evening game drives and exploring the abundant wildlife, diverse flora, and dramatic coastlines of the Eastern Cape.

Days 12-13: Eastern Cape Safari

Elephant cuddle
Elephant cuddle

Start your day with an early morning wake up call. Enjoy a cup of coffee and homemade baked goods as you drive along the landscape in search of wildlife. 

The game reserve houses a complex and diverse ecosystem, with over 60 species of mammal (including the Big 5) present in the park. Lions, elephants, cheetahs (only 7,000 left in the wild!) and giraffe all call this landscape home. On the plains, you'll find herds of game animals including zebra, black wildebeest, red hartebeest, oryx, and eland (to name a few). 

As the day draws to a close, nocturnal species begin to forage. Rangers will shine spotlights on your way back to the lodge to spot aardvark, endangered brown hyena, and others. 

Birding enthusiasts will love spending time on the Bushman's River, which winds its way through the reserve. Enjoy a peaceful boat cruise and see if you can spot some of the area's 239 bird species. For the serious birder, local highlights include Knysna turacos, secretary birds, Denham's Bustard, and an array of barbets, woodpeckers, and sunbirds.

In the evening, enjoy a fire and local cuisine as you share stories of your day beneath a canopy of stars.

Day 14: Depart Eastern Cape via Cape Town

Say goodbye
Say goodbye

After your last game drive and breakfast at the lodge, drive to Port Elizabeth and board your flight to Cape Town. From here, catch your flight home.


Map of South Africa Road Trip: Cape Town, Winelands, Garden Route, & Eastern Cape Safari - 14 Days
Map of South Africa Road Trip: Cape Town, Winelands, Garden Route, & Eastern Cape Safari - 14 Days
Written by Sonya Pevzner, updated Feb 18, 2021