See some of the highlights of Cape Town with this five-day trip. You'll cover plenty of ground—and even some waves—as you ride a sidecar, sea kayak, bicycle, and cable car through Cape Town's scenic surroundings.

Highlights

  • Ride a sidecar down the coast to the Cape of Good Hope
  • Paddle around Moullie Point on a sea kayak tour
  • Look down at the city from atop Table Mountain
  • Cycle through the vineyards of the Winelands

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Cape Town Cape Town
Day 2 Guided Cape Peninsula Sidecar Tour Cape Town
Day 3 Guided Sea Kayak & Table Mountain Tour Cape Town
Day 4 Guided Bike Tour of the Winelands Franschhoek
Day 5 Depart 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 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 3: 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.

Day 4: 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 5: Depart Cape Town

Take to the skies
Take to the skies

Transfer to the airport for your connecting flight home.

Map

Map of South Africa Adventure: Cape Town & Winelands - 5 Days
Map of South Africa Adventure: Cape Town & Winelands - 5 Days