Two Weeks in South Africa

Cape Town, the Cape Winelands and the Garden Route

From December to April (summer and early fall), when the weather is settled and reliably sunny, Cape Town is one of the world’s most beautiful cities, with its dramatic mountains, white-sand beaches, subtropical vegetation and a colorful downtown district, the Victoria & Alfred Waterfront. Less than an hour’s drive away, the Franschhoek Valley is arguably the most scenic wine-growing area in the world. To the south, the coastal town of Hermanus is set in the Cape Floristic Region, an area with an extraordinary number and great diversity of endemic plant species. The Garden Route begins 190 miles to the east at Mossel Bay, and from there the famously picturesque road follows the Indian Ocean coastline for 185 miles to Storms River. 

This two-week itinerary begins in Cape Town, takes in the Cape Winelands and Plettenberg Bay, the most dramatic area of the Garden Route, and culminates in Cape Town. For the latest on Cape Town, including a full review of The Silo hotel, read the August 2018 issue of the Hideaway Report. 

Itinerary Highlights

Our itineraries are for your inspiration. Please contact a travel advisor to customize this itinerary to fit your needs.

  • Visit the Zeitz Museum of Contemporary Art Africa
  • Tour Robben Island, where Nelson Mandela was imprisoned
  • Stop at the leading wineries of Franschhoek
  • Whale watch in Hermanus
  • Explore the Kirstenbosch National Botanical Garden
  • Hike a trail on the Garden Route
  • Drive around scenic Table Mountain

Trip Overview

Day 1 : Cape Town
Settle in to The Silo
Day 2 : Cape Town
Shop the Watershed and tour the Zeitz Museum
Day 3 : Cape Town
Tour Robben Island
Day 4 : Cape Winelands
Visit Franschhoek Wine Valley
Day 5 : Cape Winelands
Relax at La Residence and tour wineries
Day 6 : Hermanus
Whale watch in Hermanus
Day 7 : Hermanus
Visit the Old Harbour Museum or the Fernklook Nature Reserve
Day 8 : Gansbaai
Visit the Grootbos nature reserve
Day 9 : Gansbaai
Enjoy a botanical safari
Day 10 : Plettenberg Bay
Enjoy the views at The Plettenberg hotel
Day 11 : Plettenberg Bay
Hike a trail on the Garden Route
Day 12 : Cape Town
Have a formal dinner at Ellerman House
Day 13 : Cape Town
Drive around Table Mountain
Day 14 : Return home
Shop for South African wine, then board your flight

Day 1 : Cape Town

On arrival, after your overnight flight, head for The Silo, a stunning contemporary hotel set in the repurposed elevator tower of a historic grain silo complex above the adjoining Zeitz Museum of Contemporary Art Africa. From your room, the views of the marina, the lively V&A Waterfront and an expanse of the South Atlantic are unforgettable. The Silo has vibrant modern interiors augmented by a private art collection. Having settled in, head to the sensational rooftop restaurant for lunch. In the afternoon, relax by the rooftop swimming pool with its unimpeded view of Table Mountain, or adjourn to the spa. In the evening, enjoy a cocktail at the hotel’s lively The Willaston Bar, followed by dinner at the adjoining The Granary Café, which serves “honest and approachable food that showcases seasonal, local ingredients.”

The Zeitz Museum of Contemporary Art Africa in Cape Town
The Silo

Designed by London-based architect Thomas Heatherwick, this stunning contemporary hotel is set in the repurposed elevator tower of a historic grain silo complex above the adjoining Zeitz Museum of Contemporary Art Africa.

Day 2 : Cape Town

After a lavish breakfast at The Granary Café, take a stroll around the V&A Waterfront and pay a visit to The Watershed, a renovated marketplace with more than 150 local designers, craft booths and textiles vendors. Following a light lunch at one of the numerous local fish restaurants, head to the Zeitz Museum of Contemporary Art Africa. (Given sufficient notice, the concierge at The Silo can arrange a private tour with one of the curators.) As well as containing the world’s most comprehensive collection of African modern art and sculpture, the museum is an architectural tour de force. 

Cape Town has become one of the world’s foodie cities, so this evening have dinner at The Test Kitchen, where chef Luke Dale-Roberts has acquired an international reputation. Reservations can be hard to come by, so an alternative might be The Pot Luck Club, its more casual sister restaurant.

"Untitled (Dress from Moyo)" by Kudzanai Chiurai in collaboration with Marianne Fassler - Photo by Hideaway Report editor

Day 3 : Cape Town

This morning leave for the three-and-a-half-hour boat tour to Robben Island, for 18 years the place of Nelson Mandela’s imprisonment. The culmination of the trip is a visit to his tiny cell, with its barred windows, single lightbulb and bedroll on the floor. Boats depart for Robben Island from the V&A Waterfront at 9 a.m., 11 a.m. and 1 p.m. daily. In the afternoon, pay a visit to the world-renowned Kirstenbosch National Botanical Garden, founded in 1913 to preserve the country’s unique flora and to cultivate indigenous plants. In the evening, have dinner at Aubergine, set within a charming 19th-century house, near Company’s Garden (founded by the Dutch East India Company to supply its passing ships).

The view of Table Mountain, left, and Robben Island, right, in Cape Town

Day 4 : Cape Winelands

One of the most appealing aspects of Cape Town is its proximity to the wine country, less than an hour’s drive away. More than 100 wineries and numerous Cape Dutch farmsteads dot the spectacular landscape. This morning, drive out to the unspoiled town of Franschhoek, “French corner” in Afrikaans, which was founded in 1688 by Huguenot refugees. Explore its delightful main street, with its bookstores, galleries and antiques shops, and then have lunch at one of the small bistros. Later, check into La Residence, a lavish Tuscan-style villa-hotel set amid a 30-acre wine estate. Its 11 magnificent suites offer panoramic views of the valley, vineyards and mountains. Decorative touches include antiques, rich fabrics, chandeliers, four-poster beds, vaulted ceilings and original artwork. Have dinner in the hotel’s opulent dining room with its fine seasonal cuisine and extensive wine list.  

The entrance to La Residence in the Cape Winelands in Franschhoek
The entrance to La Residence in the Cape Winelands in Franschhoek - © The Royal Portfolio
La Residence

This beautiful Tuscan-style villa hotel is nestled amid a 30-acre wine, olive and plum estate in the Franschhoek Valley.

Day 5 : Cape Winelands

Spend the morning enjoying the hotel’s facilities, including its infinity pool and spa. Tennis, golf and horseback riding are available nearby. After lunch, go on an escorted tour of some of the leading wineries in Franschhoek, plus those in neighboring Stellenbosch and Paarl. Take the opportunity to try wines made from Pinotage, South Africa’s signature grape variety. Franschhoek has become a gastronomic center, and there are numerous exceptional restaurants. For dinner, consider La Petite Colombe at Le Quartier Français hotel, the sister restaurant of the world-renowned La Colombe in Cape Town.

View of a vineyard in the Cape Winelands of South Africa
View of a vineyard in the Cape Winelands of South Africa - jaap-willem/iStock/Getty Images E+

Day 6 : Hermanus

From Franschhoek it is a scenic 60-mile drive south to Hermanus, overlooking the Indian Ocean. Every year from June through December, Walker Bay and the surrounding waters host hundreds of southern right whales, which come to mate and calve. Nearby Dyer Island and Geyser Rock are home to vast colonies of seals and penguins. These are favorite foods for great white sharks, which are present in such numbers that the strait between the islands has earned the name Shark Alley. Their presence is not dependent on the season, and they can be seen either from a boat or (for the intrepid) a submerged cage.

Check into Birkenhead House, a stylish contemporary boutique hotel on a rocky promontory overlooking Walker Bay. The 11 studio suites are contained within three houses. A wall of glass in the hotel lounge provides a sensational view of the bay, while a dramatic deck has an infinity-edge plunge pool. After a light lunch, either relax by the pool or indulge in a spa treatment. Have dinner in the excellent seafood-oriented restaurant, where chef Oliver Coetzee offers a menu with a strong Malay influence and pan-Asian flavors. 

The lounge at Birkenhead House in Hermanus
The lounge at Birkenhead House in Hermanus - © The Royal Portfolio
Birkenhead House

This stylish contemporary boutique hotel on a rocky promontory overlooking Walker Bay and two attractive beaches is 90 minutes southeast of Cape Town.

Day 7 : Hermanus

After breakfast, explore the town on foot and pay a visit to the Old Harbour Museum, where old fishing boats and reconstructed fishermen’s shacks are a reminder of the town’s heritage. On a sunny day, you may wish to have a beach picnic prepared by the hotel. The beach to the left of the hotel, Voëlklip (“Bird Rock”), is ideal for swimming and sunbathing. Grotto Beach is the longest strip of white sand in Hermanus and lies to the east of Birkenhead House, an easy 10-minute walk away along a clifftop path. Alternatively, those interested in botany may wish to visit Fernkloof Nature Reserve, where more than 1,250 plant species have been collected and identified. More-adventurous travelers can take a boat trip to see the great white sharks.

Aerial view of Grotto Beach in Hermanus
Aerial view of Grotto Beach in Hermanus -

Day 8 : Gansbaai

The southern coast of South Africa is separated from the interior by a range of mountains. This coastal zone is covered by a carpet of low evergreen shrubland known as fynbos, which shelters a huge variety of spectacular flowers. 

It is a mere 25 minutes’ drive from Hermanus to Gansbaai, where you will check in to Grootbos Private Nature Reserve. There, two lodges and two villas are set on a hillside with a dramatic view over the dunes of Walker Bay. Large bedrooms provide fireplaces, four-poster canopy beds, private wooden decks and spacious baths with soaking tubs and separate showers. In the afternoon, relax in the spa or go for an escorted beach hike.

Luxury Suite at Grootbos Private Nature Reserve in Gansbaai
Luxury Suite at Grootbos Private Nature Reserve in Gansbaai - Courtesy of Grootbos Private Nature Reserve
Grootbos Private Nature Reserve

Set on a hillside overlooking the dunes of the seasonal whale-watching center of Walker Bay, this property encompasses two lodges and a six-room and a four-room villa.

Day 9 : Gansbaai

After breakfast, head off on a 4x4 botanical safari in an open-top Land Rover. The resort’s 6,200 acres of pristine wilderness contain 800 recorded plant species. Return to the lodge for lunch. In the afternoon, either relax beside the pool or venture out on a horseback excursion. 

Botanical safari at Grootbos Private Nature Reserve in Gansbaai
Botanical safari at Grootbos Private Nature Reserve in Gansbaai - Courtesy of Grootbos Private Nature Reserve

Day 10 : Plettenberg Bay

From Gansbaai, it is a 270-mile drive east to Plettenberg Bay. On arrival, check into The Plettenberg hotel, situated on a rocky headland with impressive views of the sea, shore and mountains. The 35 guest quarters are individually styled, and amenities include a spa and two infinity pools. Have dinner on the outdoor scenic terrace at SeaFood at The Plettenberg, overseen by talented chef Peter Tempelhoff. 

Premier Suite at The Plettenberg in Plettenberg Bay
Premier Suite at The Plettenberg in Plettenberg Bay - Courtesy of The Plettenberg
The Plettenberg

This renowned hotel situated on a panoramic rocky headland in Plettenberg Bay has stunning views of sea, shore and mountains.

Day 11 : Plettenberg Bay

Today, head out to explore the most eye-catching segment of the Garden Route. Just east of Plettenberg Bay, the landscape becomes extremely dramatic, with forests, rocky peaks, gorges, waterfalls and sheer cliffs plunging into the sea. Known as Tsitsikamma, this area was once a national park in its own right, but in 2009 it was incorporated into the larger Garden Route National Park. This is the setting for one of the finest hiking routes in South Africa, the challenging five-day Otter Trail. However, there are shorter, more easily accessible routes. For example, the Pied Kingfisher Trail, which starts from the Ebb and Flow Rest Camp in the Wilderness section of the park, takes three to four hours to complete.

Aerial view of the Tsitsikamma cliffs in Garden Route National Park near Plettenberg Bay
Aerial view of the Tsitsikamma cliffs in Garden Route National Park near Plettenberg Bay - JanRoode/iStock/Getty Images Plus

Day 12 : Cape Town

This morning drive east along the coast for two hours to the city of Port Elizabeth. From there, board a 90-minute flight back to Cape Town. Upon arrival, head for Ellerman House, a mansion oasis overlooking the sea in upscale Bantry Bay. Once the home of a shipping magnate, the Edwardian-style residence has been transformed into a superlative 13-room hotel. Most of the accommodations open onto private verandas with views of the sea. Enjoy an evening cocktail overlooking the ocean and then head indoors for a dinner of Cape and European cuisine served in a formal dining room. 

Villa One at Ellerman House in Cape Town
Villa One at Ellerman House in Cape Town - © Etched Space
Ellerman House

This distinguished mansion oasis overlooking the sea in upscale Bantry Bay is a 15-minute drive west of Cape Town.

Day 13 : Cape Town

Today, if you are feeling energetic, make a counterclockwise circuit of Table Mountain through the astonishingly dramatic landscape. Drive southwest, through Clifton, and pause for a coffee overlooking the white sands of Camps Bay before continuing south along the rugged, wave-dashed Atlantic Coast to picturesque Hout Bay. Then head back through Constantia, the city’s most desirable residential neighborhood, past the University of Cape Town to the center of the city. In the evening have dinner at La Colombe, located on the Silvermist organic wine estate, which is widely regarded as one of the finest restaurants in South Africa. Chef Scot Kirton’s menus follow the seasons but run to dishes such as langoustine with quail egg, ponzu and a traditional egg custard; bavette steak with broccoli, zucchini, pickled red onion and Bolognese sauce; and lamb tongue with eggplant, mussels, chorizo and spring onion.

The pool at Ellerman House in Cape Town
The pool at Ellerman House in Cape Town - © Etched Space

Day 14 : Return home

As this is your final day, take the opportunity to relax in the garden of Ellerman House, with its wonderful view of the ocean. However, if you want to bring home some South African wines, you may wish to visit Caroline’s Fine Wine Cellar on Strand Street, downtown. Started by Caroline Rillema in 1997, this is where you will find big-name wines such as Rust en Vrede, Warwick, Delaire Graff, Hamilton Russell and Boekenhoutskloof, among others. In the late afternoon, head to the airport for your long flight home.


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