South Africa Western Cape Getaway: Cape Town & Winelands - 8 Days

Day 1: Arrive in Cape Town, Explore at Leisure

Welcome to the legislative capital of South Africa, Cape Town, nestled between the dramatic peaks of Table Mountain and the shimmering waters of the Atlantic Ocean. Meet your driver outside the airport and transfer to your hotel to check in and freshen up. The rest of the day is free, so you can explore the city at your own pace. A good place to start is the V&A Waterfront, named after Queen Victoria and Prince Albert. This bustling harbor is home to an array of attractions, including the Two Oceans Aquarium, where you can marvel at marine life from both the Atlantic and Indian Oceans.

Continue to The Watershed, a dynamic market space featuring over 150 stalls housed in a historic grain silo. Peruse the stalls lined with handcrafted jewelry, locally made home decor, and traditional crafts, then grab a cup of coffee from one of the on-site cafés. When the sun starts to set, take a ride on the Cape Town Wheel for panoramic views of the waterfront cast in a golden glow. As darkness falls, find a restaurant overlooking the water for a delicious dinner. The city's coastal location means fresh seafood is abundant, so consider trying dishes like grilled snoek (a local fish), calamari, or mussels.

Day 2: Guided Tour of Cape Town & Table Mountain

Join your guide today for a private tour of Cape Town's highlights, starting with a cable car ride up Table Mountain. The cable car rotates, so you'll get a 360-degree view of the cityscape below as you ascend. At the top, explore the different viewpoints overlooking the city, its rugged coastline, and the dramatic peaks of the Twelve Apostles. Ride the cable car back down the mountain and head to Bo-Kaap, the Malay quarter, renowned for its brightly colored houses. After a leisurely stroll down the cobblestone streets, continue to Greenmarket Square in the heart of the city.

Wander through the historic square lined with colorful stalls selling everything from traditional crafts and intricate jewelry to handwoven textiles and wood carvings. Your next stop is the nearby Adderley Street Flower Market, where you can shop for fresh flowers like delicate orchids and seasonal blooms. End the tour at the Castle of Good Hope, the oldest surviving colonial building in the country, built between 1666 and 1679 by the Dutch East India Company. Discover the castle's robust stone walls, bastions, and moat while you learn about its rich history.

Day 3: Full-Day Cape Peninsula Tour 

Leave the city behind for the day as you set off on a full-day private tour of the surrounding Cape Peninsula. Start on Chapman's Peak Drive, a scenic coastal road that will take you to Cape Point, the peninsula's tip. Here, you'll see the iconic Cape Point Lighthouse, which you can climb for panoramic views of the surrounding coastline and glittering ocean. Continue to Boulder's Beach to meet the resident penguins. The beach's protected environment ensures the penguins are safe from predators, so you can enjoy an unobstructed view of their playful antics and social behaviors.

After marveling at the penguins, head to the nearby Simon's Town, known for its well-preserved naval base and colonial architecture. Stroll the picturesque streets lined with colorful Victorian buildings and find a restaurant for lunch. On your way back to Cape Town, stop at Hout Bay, nestled between the rugged Chapman's Peak and the Atlantic Ocean. Back in the city, make one last stop at the Kirstenbosch National Botanical Gardens to wander through the themed areas and traverse the Centenary Tree Canopy Walkway.

Day 4: Free Day in Cape Town: Robben Island & Apartheid History

Today is free for you to spend as you wish, with plenty of museums, sightseeing, and adventure options available. If you're looking for an adrenaline rush, you could soar above the city on a tandem paragliding flight or skydive. Those who want to dive deeper into the country's recent past can return to the V&A Waterfront to board a ferry to Robben Island, home to an Apartheid-era prison that was used to hold political prisoners like Nelson Mandela. Join a tour of the former prisoner facilities, where knowledgeable guides—many of whom were former inmates—share their personal stories and experiences.

The tour can be an emotional experience, but it allows you to understand the harsh conditions endured by prisoners and the resilience they showed in their fight for justice. Afterward, go for a leisurely stroll around the island, taking in views of Cape Town's skyline. If museums are more your thing, consider visiting the District Six Museum, dedicated to preserving the memory and legacy of a neighborhood that was forcibly cleared during Apartheid. Through engaging displays and oral histories, you'll gain insight into the vibrant District Six before its demolition and the impact of Apartheid policies on its inhabitants.

Day 5: Whale Watching Cruise, Explore Overberg & Stony Point Nature Reserve

Trade Cape Town's bustling streets for the shimmering waters of the Atlantic this morning as you transfer two hours to Overberg, where you'll board a whale watching cruise. As your captain navigates the waters in search of the Marine Big Five (the southern right whale, shark, dolphin, seal, and penguin), you'll learn about the area's marine ecosystem and the behaviors of the creatures you have a chance to see today. As you scan the horizon, you may catch sight of a fin or tail bobbing above the water, so keep your eyes peeled.

Though southern right whales are most commonly seen in the area, you may also spot humpback whales, Bryde's whales, and orcas, depending on the time of year you're visiting. After the boat tour, dock back in Overberg and head to the cliffside to try to catch another glimpse of the resident whales. The crashing waves have carved a series of caves that you can explore, or go for a refreshing swim in the Atlantic. Head to the charming village of Stanford for lunch, then end your tour in Stony Point Nature Reserve, renowned for its African penguin colony.

Day 6: Transfer to Franschhoek, Free Afternoon in the Cape Winelands

Say goodbye to Cape Town this morning as you set off on a 1.5-hour transfer to Franschhoek, nestled within the scenic Cape Winelands, South Africa's renowned wine country. When you arrive, the rest of the day is yours to spend as you wish. You could stay in town, where you'll find plenty of gourmet restaurants, local markets, museums, and spas. Or, take a ride on the Franschhoek Wine Tram, an open-air tram that takes you on a scenic journey through the rolling vineyards and picturesque landscapes of Franschhoek Valley.

The tram's route includes stops at celebrated vineyards such as Groot Constantia, Vrede en Lust, and Chamonix, where you can sample fine wines, learn about the winemaking processes, and enjoy the natural beauty of the countryside. Grab dinner at one of the estates or return to town for a cooking class with local chef Nicola Spilsbury. Learn how to make local dishes like mussels steamed in a Cape Malay curry and a delicious melktert (South African milk tart made with just milk, sugar, eggs, and flour) for dessert. 

Day 7: Full-Day Tour of the Cape Winelands

Spend your penultimate day in South Africa exploring the Cape Winelands with a private tour, starting in Franschhoek's picturesque streets. Wander past well-preserved Cape Dutch buildings, boutique shops, and art galleries before heading to another charming town, Stellenbosch. Follow your guide down the tree-lined streets dotted with elegant buildings and surrounded by world-renowned wineries. Then, make your way to Paarl to see the mix of Cape Dutch and Victorian-style buildings and learn about how Afrikaans originated here in the 17th century. 

Drive past the Afrikaans Taal Monument, dedicated to the heritage and evolution of Afrikaans, on your way to three different wine estates. At each estate, you'll tour the cellar and vineyards while you learn about the meticulous winemaking process and the unique characteristics of each winery's varietals. Following the tours, you can enjoy a tasting session to sample a curated selection of wines. Many estates also offer gourmet dining options, so you may opt for a delicious meal paired with the perfect wine before returning to your hotel.

Day 8: Transfer to Cape Town, Depart

Now that you've spent eight days exploring Cape Town and the lush Cape Winelands, it's time to head home. Enjoy a final breakfast, then hit the road on a 1.5-hour transfer back to Cape Town. On the way, enjoy views of the towering Drakenstein and Simonsberg Mountains. When you get closer to the city, you'll see the landscape transform from rolling hills to vibrant cityscape. Head straight to the airport to make sure you're on time for your flight home. Safe travels!