Immerse yourself in South Africa and Lesotho's natural landscapes on this two-week road trip across both countries. Start in Cape Town with community development tours, a cruise to Robben Island, and a day trip down the Cape Peninsula. Then, drive yourself to Stellenbosch to explore the Cape Winelands, followed by Hermanus for a boat cruise to spot whales, sharks, seals, and penguins. From here, explore the Gondwana Private Game Reserve before ending with an epic waterfall in Lesotho.


  • Start your trip with a 14-dish traditional African dinner in Cape Town
  • Ride an e-bike through the gorgeous countryside in the Cape Winelands
  • Go on game drives and bush walks while spotting the Big Five animals
  • Drive through the dramatic and winding Sani Pass to get to Lesotho

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Cape Town (South Africa), Community Development Tour Cape Town
Day 2 Township Tour, Cruise to Robben Island, Traditional African Dinner Cape Town
Day 3 Full-Day Tour of the Cape Peninsula Cape Town
Day 4 Drive to Stellenbosch, Food Tour in the Historic Center Stellenbosch
Day 5 Cycle in the Countryside to Boschendal Wine Estate Stellenbosch
Day 6 Drive to Hermanus, Hike on the Hermanus Cliff Path Hermanus
Day 7 Boat Cruise to Dyer Island & Geyser Rock Hermanus
Day 8 Transfer to the Gondwana Private Game Reserve Herbertsdale
Days 9-10 Activities at Gondwana Game Reserve Herbertsdale
Day 11 Fly to Johannesburg, Drive to Clarens, Leisure Time Clarens
Day 12 Drive to Lesotho via the Sani Pass Lesotho
Day 13 Explore Lesotho at Your Own Pace Lesotho
Day 14 Depart Lesotho  

Detailed Itinerary

Day 1: Arrive in Cape Town (South Africa), Community Development Tour

Wander down the Victoria & Alfred Waterfront and find a good spot for dinner

Welcome to the vibrant city of Cape Town, nestled between the iconic Table Mountain and the vast Atlantic Ocean. Meet your driver outside the airport and transfer to your hotel, where you can refresh before venturing out on a five-hour tour of the city's eastern townships to learn about inspiring community development projects. This is where you'll discover South Africa's turbulent history and the challenges its residents face today.

Then, meet the unsung heroes working toward positive change in the city, from developing educational programs and skill-building workshops to sustainable agriculture and art initiatives. In the evening, make your own way to the V&A Waterfront, a bustling harbor area, to browse the array of boutiques, museums, and eateries offering local and international cuisine. Find somewhere to eat dinner, like a seafood establishment selling today's catch, overlooking the water and surrounding mountains.

Day 2: Township Tour, Cruise to Robben Island, Traditional African Dinner

Take a ferry to Robben Island to tour the maximum-security prison where Nelson Mandela was held

Dive deeper into South Africa's past today with a guided tour to one of the townships that were shaped by segregation policies from the Native Act of 1923 on the outskirts of the city. The townships are still filled with descendants of the original inhabitants who were forced to live here during the apartheid, so you can meet the locals and learn about their personal stories, struggles, and resilience. Then, explore the streets to see how residents have transformed the neighborhood into a vibrant, cultural hub. 

In the afternoon, return to the Victoria & Alfred Waterfront to catch a 40-minute ferry to the UNESCO-listed Robben Island for another guided tour, this time led by former prisoners for a firsthand account of the island's role as a political prison during the apartheid era. Follow your guide through the maximum-security prison, stopping at the cell where Nelson Mandela spent 18 years in captivity. After a day of learning about the city's dark history, sit down for a 14-dish tasting menu, inspired by recipes from across the continent. While you eat, enjoy a performance by African musicians and dancers to end the night.

Day 3: Full-Day Tour of the Cape Peninsula

Look out at the resident African penguin colony on Boulder's Beach

Leave the city behind for the day as you set off on a nine-hour tour of the Cape Peninsula, starting with a drive through the coastal suburbs of Sea Point, Bantry Bay, and Clifton. Stop at a viewpoint to see the Twelve Apostles mountain range, which forms the back of Table Mountain. After taking some pictures of the towering mountains, continue past Bakoven and Llandudno, coastal suburbs that have witnessed various shipwrecks over the centuries. Take a break from the scenic drive in the fishing village of Hout Bay, where you can join a boat tour to Duiker Island, home to thousands of Cape fur seals. 

Back in the car, follow Chapman's Peak Drive until you reach the Cape Point Nature Reserve. Climb up to the famous Cape Point lighthouse to see where the Atlantic and Indian oceans meet, then sit down for lunch at a nearby restaurant. Once you're refueled, visit Boulder's Beach to look out at the resident colony of African penguins before driving through Simon's Town and across Boyes Drive, passing the seaside villages of St James and Muizenberg. End the tour at the Kirstenbosch Botanical Gardens back in Cape Town to wander along the winding pathways through the themed gardens.

Day 4: Drive to Stellenbosch, Food Tour in the Historic Center

Set off on a walking tour through Stellenbosch to try local delights like biltong, a type of jerky

Pick up your rental car and say goodbye to Cape Town as you drive 40 minutes to Stellenbosch, a charming town in the Cape Winelands. Meet your guide in the historic center and set off on a 3.5-hour food tour to local markets, restaurants, and bars, each offering a twist on South African cuisine. Stop for a variety of sweet and savory tastings of local delights, like biltong, a flavorful cured meat, or koeksisters, deep-fried dough pastries that are twisted and coated in syrup.

Try not to fill up too much, as you have a sit-down lunch packed with seasonal, locally sourced produce to look forward to. You'll also have the opportunity to sample handcrafted beer and award-winning gin to wash everything down. Break up all the eating and drinking by exploring public art exhibitions lining the streets and learning about the town's rich history. Then, end the tour with a cup of delicious coffee paired with a decadent sweet treat.

Day 5: Cycle in the Countryside to Boschendal Wine Estate

Cycle past the lush vineyards and towering mountains surrounding Stellenbosch

Get ready for an active adventure, as you explore the Cape Winelands on an e-bike today. Navigate Stellenbosch's charming streets and vineyard-draped hills as you follow your guide through the historic Idas Valley and along the Banhoek Conservancy Trails. Look out at the majestic mountains, dense forests, and expansive vineyards while you ride, enjoying the ease the bike's electric assistance provides. Stop at Boschendal Wine Estate, nestled in the Franschhoek Valley, to take a break and enjoy a cup of coffee with a snack. 

Plan your trip to South Africa
Chat with a local specialist who can help organize your trip.
Don't worry about pedaling back, as a bus will be waiting for you outside the estate to transfer you to town. The rest of the afternoon is then yours to spend as you wish. You could visit another winery for a tour and tasting flight or head to the Stellenbosch University Botanical Garden, home to a diverse collection of South African plants. Wander through the themed sections, each showcasing different aspects of the country's rich flora, and stop in the cycad amphitheater to see ancient plants. In the evening, wander down the historic Dorp Street to find somewhere for dinner.

Day 6: Drive to Hermanus, Hike on the Hermanus Cliff Path

Keep an eye out for southern right whales as you trek along the Hermanus Cliff Path

Trade the countryside for the seaside today as you hop in your rental car and drive 1.5 hours down the coast to Hermanus, renowned as one of the best land-based whale watching destinations in the world. After settling into your hotel, the rest of the day is yours to spend as you wish. If you're up for an active adventure, you could set off on a 7.4-mile (12 km) hike down the Hermanus Cliff Path. Follow the rugged coastline lined with local plants and coastal flora to look out at the expansive Walker Bay.

Keep your eyes peeled on the water, as southern right whales often make an appearance here from June to November. You can walk the entire path, which normally takes three to four hours, or just a portion, turning back to town when you're ready. Return to the hotel to refresh, then wander through town to see the art galleries, boutiques, eateries, and markets. Shop for souvenirs or sit down to savor local delights, like grilled line fish or Cape Malay-style picked fish.

Day 7: Boat Cruise to Dyer Island & Geyser Rock

Walk around Geyser Rock, covered in a colony of 60,000 Cape fur seals

If you didn't get to see any whales from land yesterday, don't worry, as today you'll set off on a boat tour to get up close and personal with these magnificent creatures. Transfer to the coastal town of Gansbaai to board the boat at Kleinbaai Harbor, then cruise 5 miles (8 km) offshore to Dyer Island, a protected area known as the "Great White Shark Capital." Look out at the resident African penguins and the neighboring Geyser Rock, home to over 60,000 Cape fur seals year-round. After seeing the penguins and seals, cruise down the channel between the islands to look for great white sharks and whales.

Depending on the time of year you visit, you may see humpback whales, southern right whales, and even orcas. Back on land, transfer to your hotel to rest, or venture out to explore more of the area on your own. If you want to relax, head to Grotto Beach to walk along the golden sounds and take in panoramic views of the surrounding mountains. When you get too hot, the calm waters of Walker Bay will welcome you. In the evening, stroll along the waterfront, dotted with international and local restaurants, to find somewhere for dinner.

Day 8: Transfer to the Gondwana Private Game Reserve

Spend your first night in the Gondwana Private Game Reserve looking up at the stars

Say goodbye to Hermanus this morning, as you head to the Gondwana Private Game Reserve. To get there, you can drive the three hours yourself or have a private driver take you. If you don't want to drive, transfer two hours back to Cape Town, catch a one-hour flight to George Airport, then a 45-minute transfer to the reserve. When you arrive, settle into your lodge, then enjoy the rest of the day at your own pace. A good place to start is the visitors' center, where you can meet the friendly staff and discover all the activities available to you. 

While you're there, learn about the reserve's ongoing conservation efforts through interactive displays and audiovisual presentations. Sign up for some guided tours, like a game drive or bush walk, or ease yourself into the park with a stargazing tour, led by passionate astronomers armed with telescopes. Away from the glow of the city lights, the reserve offers optimal conditions for stargazing, so you can see the brilliance of the stars in their full glory. The astronomer will point out planets and constellations while teaching you about mythological tales and celestial scientific insights.

Days 9-10: Activities at Gondwana Game Reserve

Search for members of the Big Five and zebras as you explore the reserve

Spend the next two days exploring the reserve, choosing from an array of activities to discover the area and its wild inhabitants. One of the most popular activities is a game drive to spot the free-roaming Big Five animals, which includes lions, leopards, rhinoceros, elephants, and African buffalo. Mountain biking is also popular here, as the park has plenty of routes, ranging from novice to advanced, so anyone is welcome to rent a mountain bike and pedal down the rugged terrain with a guide to look for more wildlife.

If you want to explore the park on foot instead, join a guided bush walk to traverse the untamed landscape. Listen as your guide teaches you about the park's rich ecosystem and how to follow the animal tracks covering the winding trails. Bird-watchers can also thrive here, as the reserve is home to 42 of South Africa's 53 endemic bird species. Grab your binoculars and follow your guide through dense forests and open plains to look for birds like raptors, songbirds, or waterfowls flying overhead or nestled in the foliage.

When you're ready to just relax, visit the on-site spa and choose from a full-treatment menu utilizing luxurious African products and plants. You could even have your treatment outside to continue connecting with nature. Finally, if you want to contribute to the reserve's conservation efforts, spend an hour removing invasive black wattle trees from the landscape, as they consume excessive amounts of water and alter soil composition. 

Day 11: Fly to Johannesburg, Drive to Clarens, Leisure Time

Hike through Golden Gate Highlands National Park at your own pace

If you still have your rental car, drive yourself to George Airport this morning. If not, meet your driver at the reserve for a private transfer. When you arrive, catch a two-hour flight to Johannesburg, South Africa's biggest city. Pick up another rental car at the airport and drive 3.5 hours south to the town of Clarens, nestled in the foothills of the Maluti Mountains. You only have one day here, so use your free time wisely. If you want to get back into nature, head to Golden Gate Highlands National Park, just 20 minutes outside of town.

Follow one of the many hiking trails, offering panoramic views of the mountains and surrounding valleys, to spot wildlife like zebras, eland, and colorful bird species. Try to time your visit for sunset to watch the golden sandstone cliffs glow from the dying light of the sun. In the evening, return to Clarens to wander through the main square lined with restaurants, cafes, and pubs with outdoor seating. Try South African delights like bobotie, a savory spiced minced meat dish with an egg-based topping, or potjiekos, a slow-cooked stew with a variety of meats, vegetables, and spices.

Day 12: Drive to Lesotho via the Sani Pass

Follow the winding roads of the Sani Pass to get to Lesotho

Bid farewell to Clarens this morning, as you set off for your final destination, Lesotho, a landlocked country nestled within South Africa. The drive normally takes five hours, but you can take a longer route to cross the Sani Pass, one of the most scenic mountain passes in Africa. The journey from Clarens takes you through the scenic Drakensberg Mountains until you reach the base of the Sani Pass, where you can present your documents to border patrol to enter Lesotho at the end of the pass. Although the route is only 5.5 miles (9 km), the winding roads and steep gradients make it seem a lot longer.

As you ascend, watch as the landscape transforms into a panorama of rugged cliffs, deep valleys, and cascading waterfalls. When you reach the halfway point, you'll come across a viewpoint, where you can park to really take in the natural beauty of the Khomazana Valley. Back in the car, the road gets steeper, so you may experience altitude sickness. At the top, Lesotho border control will be waiting for you to show the necessary documents. Once you're welcomed in, head to your hotel to rest after the long, thrilling drive. 

Day 13: Explore Lesotho at Your Own Pace

Stop at Katse Dam to see the engineering marvel that supplies water to Lesotho and South Africa

Your penultimate day in Lesotho is yours to spend as you wish, and there's plenty to do here, despite the country's small size. If you're not tired of driving, you can explore more of the country's winding passes, like the Pass of Jackals or God Help Me Pass—just don't let the names scare you away. Those who prefer to explore on foot can set off on a hike through Tsehlanyane National Park, characterized by its lush valleys, towering sandstone cliffs, and diverse plant life. Follow the winding trails through dense forests of trees to reveal rare plant species, like the spiral aloe.

The highlight of the park is Tsehlanyane Waterfall, where rushing water cascades over rocky cliffs. You can't swim here due to the strong currents, but you can admire the natural spectacle from the shore. On your way back to the park's entrance, look out for unusual bird species, like the bearded vulture or the endemic Drakensberg rockjumper. Before returning to your hotel, stop at Katse Dam, one of the highest dams in Africa. From the observation deck, look out at the vast reservoir surrounded by mountain peaks, then join a tour at the visitor center to explore the inside of the dam and learn about its construction. 

Day 14: Depart Lesotho

Finish the trip with an inspiring visit to Maletsunyane Falls

After spending two weeks exploring South Africa and Lesotho's natural beauty, your journey comes to a close today. If you have some time before your flight, drive to Maletsunyane Falls, one of the highest single-drop waterfalls in Africa, standing at 630 feet (192 m). Admire the falls from the surrounding viewpoints or get up close and personal with the cascade by abseiling down the rock face surrounded by the cool mist. When it's time, drive to the airport, return your rental car, and head inside to catch your flight home. Safe travels!

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Map of Road Trip Through South Africa & Lesotho: Iconic Cities & Natural Landscapes - 14 Days
Map of Road Trip Through South Africa & Lesotho: Iconic Cities & Natural Landscapes - 14 Days