South Africa Road Trip: Cape Town, Winelands, Garden Route & Eastern Cape Safari - 16 Days

Day 1: Arrive in Cape Town, Explore the Port City at Leisure

Welcome to South Africa and the picturesque port city of Cape Town! Meet your driver outside the airport and transfer to your accommodation to unpack and unwind. After you settle in, spend the rest of the day exploring the city at your own pace. Head to the V&A Waterfront, named after Queen Victoria and her son, Prince Alfred. Wander down the promenade, shop for arts and crafts at the expansive Watershed market, or visit the Two Oceans Aquarium to explore underwater life. Another option is the Diamond Museum, which explores the history of the diamond rush in South Africa.

In the evening, join a sunset boat cruise to sail across the tranquil waters of Table Bay, with the iconic Table Mountain providing a dramatic backdrop. As the boat glides along the pristine coastline, unwind on deck with a refreshing drink while you watch the sun transform the sky into warm hues of red and orange. When darkness starts to fall, return to the shore and browse the array of eateries. Whether you're craving fresh seafood, international fare, or local delights, there's something here to suit every palate.

Day 2: Guided Bike Tour of the Cape Winelands

Start your morning with a 50-minute transfer to the Franschhoek Valley in the Cape Winelands, South Africa's lush wine country. When you arrive, jump on a bike and cycle past lush vineyards and soaring mountains surrounded by the scent of ripening grapes. If you get tired throughout the day, you can rest your legs in the support vehicle. Along the way, stop at world-renowned vineyards to sample local wines and learn about the winemaking process. Take a break in the shade of centuries-old oak trees at one of the estates to enjoy a picnic lunch of locally sourced delicacies.

After your picnic, head to your hotel in Franschhoek, where you can relax for the rest of the day or refresh before venturing into town to explore on your own. Visit some of the eclectic boutiques, craft markets, or antique stores in the center to find unique souvenirs, or head to the Huguenot Monument and Museum. Step inside and browse the artifacts, documents, and exhibits that provide insight into the arrival of the French Huguenots, who were fleeing religious prosecution in the 17th century. In the evening, treat yourself to a well-deserved dinner at one of the restaurants along the main street.

Day 3: Guided Cape Peninsula Sidecar Tour

After a restful night in Franschhoek, set off on a full-day sidecar tour along the Cape Peninsula, which juts out into the Atlantic Ocean at the southwestern extremity of Africa. At the southern end of the peninsula is Cape Point and the Cape of Good Hope. On the northern end is Table Mountain, overlooking Cape Town. The southernmost point of the Cape Peninsula has outstanding flora and fauna and is part of the UNESCO-listed Cape Floristic Region. Pass Cape Town University and make your way to the coastal suburb of Noordhoek.

Stop here for a coffee break and some photos, then visit the Cape Point Nature Reserve, where you'll see the Cape of Good Hope and its iconic lighthouse. Continue to Simon's Town to see the penguin colony nearby on Boulder's Beach before breaking for lunch at a local seafood restaurant along the water in the sleepy fishing town. In the afternoon, follow the scenic Boyes Drive, which climbs the lower slopes of Muizenberg Mountain, to get to the Constantia Winelands. Pick from the many wineries to experience another South African wine tasting, then return to the city in time for dinner.

Day 4: Sunrise Kayak Ride, Cable Car Up Table Mountain

Start your morning off with a sunrise kayak ride along Cape Town's pristine coastline. 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, give your arms a 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, keeping an eye out for the playful dassies sunbathing along the trail. Surprisingly, the little creatures are actually the elephant's closest living relative. Take the cable car down the mountain, then return to the V&A Waterfront, where you'll find a variety of fine dining restaurants and pubs to enjoy dinner overlooking the ocean.

Day 5: Robben Island & Zeitz Museum of African Art

In the morning, make your way to the waterfront to catch a ferry across the water to the UNESCO-listed Robben Island, located 4.3 miles (6.9 km) offshore. Meet your guide, a former inmate of the island's prison for criminals and anti-Apartheid political prisoners. Nelson Mandela, South Africa's first Black president and recipient of the Nobel Peace Prize, was imprisoned here for 18 years of his 27-year term for his anti-Apartheid activism. On the tour of the abandoned maximum-security prison, stop at his cell before exploring more of the island.

Bird-watching enthusiasts will enjoy a walk along the rugged coastline, as the island is a safe haven for about 132 species of birds, such as crowned cormorants and black-crowned night herons. After the tour, return to the mainland and spend the afternoon browsing the seven floors of the Zeitz Museum of Contemporary Art Africa, housed within a refurbished grain silo complex. Step inside and admire the array of art, from avant-garde installations to striking paintings and sculptures from around Africa and its diaspora. 

Day 6: Enjoy a Free Day in Cape Town

Take a breather with a free day to explore the city at your own pace. A good place to start is the Kirstenbosch National Botanical Gardens, one of the world's most exceptional botanical gardens. Set against the slopes of Table Mountain, this lush paradise houses thousands of species of indigenous and exotic plants. Walk along the elevated curved steel and timber Centenary Tree Canopy Walkway to enjoy panoramic views of the lush garden and surrounding mountains. 

Next, head to Bo-Kaap, the city's Malay district. Wander through the colorful streets and visit the Atlas Trading Company, a family-owned spice shop that's been in operation since 1946. Sample local delights like a fragrant curry or bobotie, a savory dish made with spiced minced meat topped with an egg and milk custard. Those who want a more adventurous day can soar above the city on a tandem paragliding flight instead. Complete a safety briefing, then jump off the mountainside to glide above the rugged cliffs and sparkling ocean as you look down at the cityscape below.

Day 7: Drive to Greyton, Explore at Leisure

Pick up your rental car or opt for a hotel delivery, then hit the road for a two-hour drive to the quaint village of Greyton. Follow 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, then spend the rest of the day exploring on your own. If you're looking for an active adventure, go on a hike through the Greyton Nature Reserve, one of the largest reserves in the Western Cape.

Follow one of the well-marked trails through colorful wildflowers and indigenous trees, looking out for birds like the Cape sugarbird or African fish eagle. Those who just want to relax can wander through the town, visit a spa, or stop for a treat at Von Geusau Chocolates. The boutique chocolate shop is a haven for chocolate lovers, as it's full of handcrafted treats crafted from the finest Belgian chocolate and locally sourced ingredients. Sample dark and milk chocolates in flavors like Frangelico, rose geranium, and maraschino cherry.

Day 8: Drive to Oudtshoorn Along Route 62

After just one night in Greyton, hit the road again for a four-hour drive east on the famous Route 62 to the town of Oudtshoorn. Modeled after America's Route 66, Route 62 brings its own South African flair and distinct local character. More than just dive bars, farm stalls, or small country towns, the road is full of surprises, like 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 stall, complete with a proudly hand-painted sign.

Mischievous friends took it upon themselves to amend the sign, ultimately convincing Ronnie to scrap the farmstand 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. Other notable attractions along the way include the Ladismith Cheese Factory and the Barrydale Heritage Garden. Arrive in town later in the afternoon and enjoy a relaxing evening. 

Day 9: Visit the Cango Ostrich Show Farm & Cango Caves

Find out why Oudtshoorn is nicknamed the "Ostrich Capital of the World" today as you drive along the highway, passing 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. Stop at the Cango Ostrich Show Farm for a glimpse into the farming industry and to come face-to-beak with the world's largest birds 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 paintings from the Indigenous Khoekhoe group. Or, to test your agility and contortion skills by choosing the adventure tour, where a series of tight squeezes and wiggles lead through narrow limestone chimneys on a memorable adventure. If there's time later, go on a game drive in the Buffelsdrift Private Game Reserve to catch glimpses of the area's resident wildlife. Back in Oudtshoorn, round out your day with ostrich steaks or kebabs at one of the town's many eateries.

Day 10: Drive to Knysna, Explore at Leisure

Say goodbye to Oudtshoorn this morning and set off on a two-hour drive down the coast to Knysna, a popular stop on the Garden Route. Drive past rolling hills, lush forests, and dramatic mountain ranges. Stop in the town of George to grab a bite to eat, then continue through the Outeniqua Pass, where you can visit one of the designated observation decks for panoramic views of the Outeniqua Mountains and vast valleys. After checking in at your hotel, spend your afternoon enjoying some of the many activities the area has to offer.

The town is a haven for outdoor adventure enthusiasts, foodies, and people seeking a quiet and relaxing getaway, so there's something for everyone. Go golfing on one of the three championship golf courses, shop for art and handmade goods, or visit the town's museums, like the Knysna Museum or Millwood House Museum. If you want to get out of town, head to the nearby Knysna Lagoon to explore the tranquil waters by boat, kayak, or standup paddleboard. In the evening, visit a local restaurant to try the fresh oysters the town is known for. 

Days 11-12: Free Days in Knysna

Beautiful landscapes and adrenaline-filled adventures go hand-in-hand for the next two days as you spend time exploring the area at your own pace. You can start your mornings with a relaxing stroll on the beach. Then, 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-foot (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 scenic hike. There are plenty of options to experience the region's beautiful nature. 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. You can also visit Monkeyland, located in Plettenberg Bay, to experience the world's first free-roaming multispecies primate sanctuary. End both days with a peaceful walk along the beach as you watch the sunset. 

Day 13: Drive to Eastern Cape Game Reserve, Sunset Game Drive

After breakfast, hit the road to your final destination, a private game reserve on the Eastern Cape. After the 4.5-hour drive, refresh at your lodge, then set off on your first evening game drive. Look out for the Big Five game animals, lions, rhinos, elephants, leopards, and buffalo as your driver navigates the diverse landscapes, from dense bushveld to expansive plains. Back at the lodge, take in the sunset views while enjoying drinks and snacks like biltong, a form of dried, cured meat—a South African favorite. 

Days 14-15: Explore Eastern Cape Game Reserve

Spend the next two days exploring the reserve, starting your days with an early wake-up call, a cup of coffee, and homemade baked goods as you drive along the landscape in search of wildlife. The reserve houses a complex and diverse ecosystem, with over 60 species of mammals present in the park. Wildlife like lions, elephants, cheetahs, and giraffes all call this landscape home. On the plains, you'll also find herds of game animals, including zebra, black wildebeest, red hartebeest, oryx, and eland. 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. As the days draw to a close, nocturnal species begin to forage. Rangers will shine spotlights so you can catch a glimpse of aardvarks, endangered brown hyenas, and African civets. Back at the lodge, enjoy a fire and local cuisine as you share stories of your day beneath a canopy of stars.

Day 16: Fly to Cape Town, Depart

After spending 16 days exploring Cape Town and driving across South Africa, your adventure comes to a close today. Enjoy breakfast at the lodge, then go on one last game drive through the reserve. Look out for animals you may have missed, like hippos and crocodiles navigating the rivers and dams. Then, return to the lodge to grab your bags and drive to Port Elizabeth, where you can drop off your rental car and board a 1.5-hour flight to Cape Town. From here, catch your flight home. Safe travels!

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