From prehistoric cave art to the cosmopolitan streets of Cape Town, this nine-day itinerary gives you a window into some of South Africa's calling cards. Start off with a walking tour through Cape Town's history and scenic drive down to the Cape of Good Hope. Continue to the Winelands to relax and sample amid the vines, then finish up searching for cave paintings and mountain trails in the Cederberg Mountains.


  • Drive the scenic Cape Peninsula out to the Cape of Good Hope
  • Take in the city and sea views from atop Table Mountain
  • Sample the fruits of Stellenbosch with an olive and wine tour
  • Follow trails through the fynbos in the Cederberg Mountains
  • Hike through the Stadsaal Caves in search of ancient art

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Cape Town, City Tour & Table Mountain Cape Town
Day 2 Atlantic Seaboard, Cape Peninsula, & Wine Tasting Cape Town
Day 3 Shark Cage Diving Adventure Cape Town
Day 4 Cape Town to Franschhoek, Afternoon Free Franschhoek
Day 5 Guided Olive & Wine Tour, Stellenbosch Franschhoek
Day 6 Franschhoek to Cederberg Mountains Cederberg
Days 7-8 Free Day in Cederberg Cederberg
Day 9 Depart Cederberg via Cape Town  

Detailed Itinerary

Day 1: Arrive in Cape Town, City Tour & Table Mountain

Cable car to Table Mountain
Cable car to Table Mountain

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. 

Meet your local guide in the city center for a 4-hour walking tour of the historic city. You'll explore the different eras of Cape Town and learn about South Africa's history, as well as the people who shaped it. Stops along the tour include the Company's Garden, Parliament, Green Market Square, The Castle of Good Hope, and the Slave Lodge.

The Company's Garden dates back to the 1650s when European settlers farmed the land to grow fresh produce to replenish ships rounding the cape. Around the corner is the Iziko Slave Lodge, a national history museum dedicated to exploring the history of slavery at the Cape. Since its construction in 1679, the building has functioned as a center for the bustling slave trade (primarily operated by the Dutch East India Company) as well as a government building and supreme court. 

Nearby sits the historic Green Market Square, which has served as a slave market, vegetable market, and center for political protests under Apartheid. These days it hosts a flea market with African souvenirs and crafts for sale.

Just down the street is the Castle of Good Hope, South Africa's oldest existing Dutch East India colonial building. On the way, you'll pass by several memorials and monuments, including the We Are Still Here Street Memorial to destitute children and the District Six Museum, which commemorates forced relocation under apartheid. 

After strolling the streets of Cape Town, stop for lunch in the city center. In the afternoon, give your legs a rest with a hop-on-hop-off tour aboard the distinctive red 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 cable car for spectacular views of the city, mountains, and ocean. Return to Cape Town in time for dinner at the bustling Victoria & Alfred Waterfront, where you'll find a variety of fine dining restaurants and pubs with views of the ocean.

Day 2: Atlantic Seaboard, Cape Peninsula, & Wine Tasting

Chapman’s Peak Drive
Chapman’s Peak Drive

Hit the road with your guide for a full-day 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.

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Head out from Cape Town early in the morning, passing Cape Town University and Constantia before heading for Ou Kaapse Weg in Noordhoek (a half-hour drive from Cape Town). 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 (an hourlong drive from Ou Kaapse Weg).

Afterward, head to Simon's Town (half-hour to the north) 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, a half-hour north of Simon's Town. Pick from the many wineries to experience a South African wine tasting, then return to the city in time for dinner. 

Day 3: Shark Cage Diving Adventure

This could be you
This could be you

Get an early start for your full-day shark diving adventure. Meet the rest of your group at the Great White House in Kleinbaai, a two-hour drive from Cape Town, where you'll gather for breakfast and a wetsuit fitting. Throughout the day, you'll be accompanied by a marine biologist and an expert crew, who will guide you on the whole experience. No previous diving experience is necessary.

Kick things off with a pre-trip safety briefing, as well as a biology lesson on the life history of great white sharks. From here, make the short walk down to the harbor to board Slashfin—a custom-designed, luxury boat named after a legendary shark with a unique dorsal fin. It's an exhilarating 20-25 minute boat ride to Dyer Island, which, together with the nearby Geyser Island, forms a narrow channel known as Shark Alley.  Keep in mind that depending on the time of year, the ride to Shark Alley can be quite cold and windy, so be sure to bring a jacket. 

After finding a suitable place to anchor, the adventure begins! You'll spend about two hours anchored, but this depends on shark activity, conditions, as well as the number of divers. After getting suited up, dive down to see the incredible animals close-up from the safety of a shark-proof cage. While you're waiting for your turn, spend time learning about the behavior of this misunderstood apex predator. You'll learn how and where the sharks feed, breed, and breach. 

Depending on the day, you'll likely also see at least two or more members of the Marine Big Five—dolphins, whales, penguins, seals, and sharks, as well as a variety of bird species. After the dive, if the weather permits, take a quick trip through the infamous Shark Alley. 

Arrive back at the Great White House, and debrief with soup and bread to warm you up. Showers are available here if you want to freshen up before heading out for your next adventure.

Return to Cape Town in the evening.

Day 4: Cape Town to Franschhoek, Afternoon Free

Franschhoek wine tram
Franschhoek wine tram

In the morning, transfer to Franschhoek, a one-hour drive from Cape Town. One of South Africa's oldest European towns, Franschhoek is nestled in the Franschhoek Valley in the mountains of the Cape Winelands. This is South Africa's heartland, with award-winning farms and wineries around every corner.

The original inhabitants of this region are the herder Khoikhoi and the hunter-gatherer San people. In the late 17th century, French Huguenot refugees arrived in the valley, bringing wine agriculture and establishing family farms. 

After checking in, spend the afternoon exploring the region and everything it has to offer. 

  • Franschhoek boasts several of South Africa's 'Top 100' restaurants and is renowned as a culinary capital. Choose from one of several excellent options and enjoy a decadent meal and world-class wine
  • Tour the area's wine cellars, many of which are housed in original Cape Dutch homesteads complete with towering oaks and rolling vineyards. From small boutique wineries to extensive cellars, the options are as varied as the wine they produce. For a wine tasting you'll never forget, take a ride on the Franschhoek Wine Tram as it winds its way through the lush valley vineyards.
  • View local and national art at the galleries lining Huguenot Road, the main shopping street in Franschhoek
  • Recharge and relax at one of the area's many luxurious spas
  • Go shopping for gifts and treasures to bring home in the town's shops and boutiques. Browse for wine, jewelry, artwork, chocolates, and more to bring back. Many of the area's wine estates also feature bakeries where guests can purchase baked bread, fresh olive oils, charcuterie, and much more
  • Visit the luxurious Val de Vie resort for a game of polo or golf at the award-winning Paarl Valley golf course 
  • Rent a bicycle and explore the area on your own, or opt for a horseback wine-tasting tour
  • Explore the Franschhoek Valley with a hike on the trails in nearby Mont Rochelle Nature Reserve

Day 5: Guided Olive & Wine Tour, Stellenbosch

A Stellenbosch vineyard
A Stellenbosch vineyard

Spend the day on a wine and olive tasting tour. Start the day with a visit to an olive oil producer for a tour of the facility. Afterward, enjoy a tasting of fresh olive oil, similar to wine tasting. There is a complex range of aromas and tastes present in olive oil, from freshly cut grass to notes of bitter walnut. 

From here, continue to a local winery for a wine tasting and tour of the historic cellar. 

After, head to the historic town of Stellenbosch, South Africa's wine and food capital. Thanks to its university, the town has a vibrant culture and youthful vibe. Stop for lunch at one of the town's many cafes and award-winning restaurants. After lunch, stroll the "Village of the Oaks", a series of shaded avenues along the creek which runs through town. As you walk through town, enjoy the views of the preserved Cape Dutch architecture.

Return to Franschhoek in the evening.

Day 6: Franschhoek to Cederberg Mountains

Stadsaal Cave
Stadsaal Cave

In the morning, transfer to Cederberg, located 2.5 hours to the north. You'll spend time at an ecological reserve that sits at the foothills of the Cederberg Mountains. Enjoy the beauty of nature and explore the area, then relax in the award-winning retreat at night.  

The region is characterized by dramatic landscapes, with striking sandstone formations, open plains, and ancient bush art sites that date back 10,000 years. The local sandstone, richly colored by iron oxides, has eroded into a variety of shapes. Hike or drive to see the well-known Wolfberg Arch, Stadsaal Caves, and the dramatic Maltese Cross

Most of the Cederberg Mountains are part of the Cederberg Wilderness Reserve and remain one of the protected wildlife areas in South Africa. Go for a hike along ancient mountain trails that wind through rare fynbos (like snow protea and Clanwilliam pincushion). 

For dinner, enjoy the fresh produce from the retreat's vegetable garden and take in the views of the vineyards and citrus groves of the Oliphants River Valley.

Days 7-8: Free Day in Cederberg

San rock art at the Stadsaal Caves
San rock art at the Stadsaal Caves

Enjoy a free day in the Cederberg area. Choose from a variety of activities to make the most of your time here. 

  • View over 130 rock art sites, some dating back to 10,000 years
  • Visit the Bushmans Kloof Heritage Center to see hunting artifacts, jewelry, dancing sticks, and musical instruments
  • Get your heart rate up with an active adventure. Go hiking, explore the area on a mountain bike ride, or cool off on the river with a canoe ride or an afternoon of fishing
  • Enjoy a wine tasting tour
  • Spend time pursuing artistic hobbies, from watercolors to photography 
  • Take advantage of the serenity to practice meditation or yoga, then top it off with an afternoon at the spa 
  • Go on a guided wildlife and birdwatching tour

Day 9: Depart Cederberg via Cape Town

Cederburg sunset
Cederburg sunset

Transfer to the airport in Cape Town for your connecting flight home.


Map of Wine & Nature in South Africa: Cape Town, Winelands, & Cederberg - 9 Days
Map of Wine & Nature in South Africa: Cape Town, Winelands, & Cederberg - 9 Days