The Whistletrip:  Itinerary 

  • Day 1:  Cape Town
  • Day 2:  Winelands day trip – Stellenbosch and Franschhoek
  • Day 3:  Cape of Good Hope day tour & hike up Table Mountain

Practical Planning

  • Schedule:  I stayed all 3 nights in Cape Town, choosing not to spend 1 in the Winelands, for two main reasons.  First, more nights in the same bed limits disruption to the flow of a whistletrip – less packing, fewer logistics, less stress.  Vacation time is too valuable.  Second, optimal sightseeing is a function of the weather.  The top of Table Mountain is often closed to visitors owing to high winds.  Chapman’s Peak Drive closes for rock fall.  Flexibility around the weather forecast is key.
  • Pack:  Be sure to take work out clothes and good shoes to tackle the Table Mountain and Cape Point trails.
  • Mobilize:   Use Uber to cover distances in the city that are too much for walking.  &Beyond arranged for a private vehicle with driver-guide for days 2 and 3, when I planned to go further afield.  Eager drivers can easily rent a car, but it was comforting to know that tastings would not be limited during a wine country visit.

Day 1:  Cape Town

Hot off the overnight flight to Cape Town, I excitedly decided to take a 3 hour hike up Table Mountain.  It was closed off owing to high winds.  Instead, I dropped my bags at home for the next 3 nights, the wonderful Cape Grace Hotel on the Victoria & Albert Waterfront, and headed to the V&A Waterfront Food Market just a 2 minute walk along the wharf.  It is filled with sleek stands, each with a different food vendor offering cuisines ranging from Italian cannoli at the Trecastelli Bakery stall to biltong, South Africa’s dried, cured meat, by the Stokkiesdraai family.  And accompanying my late lunch was a rock band was belting out terrific live tunes.

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The V&A Waterfront Food Market, perfect for finding a quick meal from artisenal vendors © The Whistletrip

Fueled up, it was time to explore the Wharf, which is situated in South Africa’s oldest working harbor.  Signs of its long history include the pretty red brick Clock Tower built in 1882 and the 18th century  Chavonnes Battery, a museum on the city’s fortifications. Now it is a bustling attraction for both residents and visitors, with upscale restaurants and stores, movie theaters, and a ferris wheel often hosting street entertainers at its feet.  Buildings are low rise and pedestrian areas are wide, giving it a relaxed, open, outdoor vibe both during the day and through the night.  2017 will witness ongoing evolution of the waterfront, with the eagerly anticipated Zeitz Museum of Contemporary Art Africa opening there in September.

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Table Mountain provides a backdrop to Table Bay Harbor and the V&A Waterfront. The red and white building is the fantastic Cape Grace Hotel © The Whistletrip
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The Cape Wheel at V&A Waterfront offers views across Table Bay Harbor © The Whistletrip

Next I walked 30 minutes from the wharf to stroll through hip restaurant and design strip, Bree Street – dubbed “Cape Town’s Coolest Block” by Vogue.  Sunday, I discovered then, was not the day to do this as everything was closed.  Cape Town is also a 9-to-5 city during the week:  if shopping is high on your priority list, you have to make time for it during the day.  Nevertheless, pressing my nose against enough windows validated that Bree Street is definitely lined with cool small galleries, boutiques showcasing jewelry and crafts beautifully blending contemporary design with traditional African motifs, and creative cocktail bars.  Meandering from there took me to Long Street, which runs parallel to Bree Street, and though just one block over, has a very different vibe with quirky hippy stores, ethnic restaurants, and hostels peppered among its Victorian buildings with their wrought iron balconies.  Continuing along Long Street, it turned into Kloof Street, lined with shops, cafes and a mix of casual and upscale restaurants covering every possible kind of cuisine.

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View from bohemian Long Street, which is lined with old buildings, cheap bars and hippy eateries © The Whistletrip

By now into the late afternoon, I hopped into an Uber to Camps Bay, an affluent suburb with waterside restaurants and white sandy beaches.  I was dropped off at Glen Beach, which sits in front of picturesque Victoria Road and is known by surfers for its powerful waves.  From there, I walked south on the sand to adjacent Camps Bay Beach, admiring the views of boulders lining the water up ahead, of clouds rolling over the Table Mountain looking up to the left, and of the sun sinking over the horizon on the right.  A beautiful sunset to end a leisurely but stimulating first day.

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Walking along Camps Bay Beach © The Whistletrip
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Sunset at Camps Bay Beach © The Whistletrip
  • Stay:  Cape Grace (5*) provides exquisitely decorated large rooms with lovely views over a quay and towards Table Mountain, welcoming service, and beautiful spaces throughout showcasing a keen eye for design details.  Rates are high, consistent with its membership of The Leading Hotels of the World, but do include fantastic buffet and a la carte breakfast options in the delightful Signal Restaurant – don’t miss the poached eggs with mushrooms on house recipe rostis.
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    Antique filled public spaces (above) and view from bedroom at Cape Grace hotel (below) © The Whistletrip
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    Contemporary art at Ellerman House © The Whistletrip

    The V&A Waterfront location (which does have other hotels) is a perfect base for exploring Cape Town on foot and having the bustling wharf on your doorstep makes it particularly appealing for solo travelers who might be nervous about venturing too far in the evenings.  Equally luxurious is Relais & Châteaux’s boutique Ellerman House.  I did not stay there but was lucky enough to visit and have heard rave reviews from trusted whistletrippers.  Its Wine Gallery is famous among oenophiles and the Contemporary Art Gallery is the owner’s private collection.  Ellerman House’s location cliff side in exclusive Bantry Bay provides wonderful ocean views but precludes walking far and rates are eye-poppingly high.  Best for honeymooners most likely to enjoy luxuriating in the seclusion.

  • Shop:  For uniquely South African products, head to  The Watershed.  This massive, open-plan industrial space on the waterfront houses 150 artisans’ stands offering a curated selection of local art, design, décor, jewelery and fashion.  A must for chic contemporary-with-a-twist home products.
  • Eat:  On any day but Sunday!  Pretty much all interesting restaurants in the heart of town are closed on Sunday nights, leaving the only real options on Camps Bay or on the V&A Waterfront, where Sevruga has a vast menu and pleasant enough food.
  • Caffeinate:  Jason Bakery on Bree Street is famous for gourmet coffees and tempting pastries.  It opens at 7am on weekdays / 8am on Saturdays.
  • Cocktail:  Blues on Camps Bay is on the second floor, so you escape the stream of people on Victoria Road and take a balcony seat to watch sunset over a glass of wine.
  • Squeeze in:  A walk through the Bo-Kaap district, just a few minutes from Bree Street’s intersection with Church Street.  Houses are brightly painted in different colors, but why this is so is unclear.  Some guides suggest that it residents were making a silent nod during Apartheid to the dream of a rainbow nation, though the painting predates the period.  Formerly known as the Malay District, its early 18th century inhabitants were emancipated slaves who had been brought by the Dutch from Malaysia, Indonesia, India, Sri Lanka.  Now it is home to a diverse Muslim community, and you can hear the call to prayer from several local mosques.

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    Brightly painted homes in the Bo-Kaap district © The Whistletrip
  • Missed Out On:  Woodstock, the hyper-trendy hipster suburb, only an 8 minute Uber ride from the city center.  It is home to the Saturday Neighbourgoods Market, which showcases over 100 local vendors offering quality foods, crafts, jewelry and clothing.  The food stalls are said to be “incredible” and the whole neighborhood is brimming with rave-reviewed restaurants such as The Pot Luck Club and The Test Kitchen, and cool cafes such as Tribe Coffee and Rosetta Roastery.  Follow advice from the locals and make time to explore the area.
  • Wish I Had:  Visited Robben Island, infamous prison of Nelson Mandela for 18 years.  Daily tours begin at Nelson Mandela Gateway at the V&A Waterfront and include a ferry ride over to the Island.  This was sold out during my visit, so book well ahead to include this in your itinerary.

Day 2:  Winelands

&Beyond arranged a driver-guide (Naz) and vehicle for days 2 and 3 so that I could explore further afield without hassle.  Since the weather was pleasant on day 2 but forecast to be spectacular the next, Naz enthusiastically recommended saving the best sunshine for a day on the Cape of Good Hope.  Table Mountain’s cable car and trails were still closed.  And so we agreed on a full day in the Stellenbosch and Franschhoek regions.

While winding past strawberry fields with bright patchwork scarecrows, Naz announced that our first stop would be the Ernie Els Winery in the Stellenbosch region.

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Scarecrows in the strawberry fields near Stellenbosch © The Whistletrip

Not being a golf expert, I assumed this was unlikely to be my speed – and I was wrong.  The views across the Helderberg Mountains are absolutely spectacular, and it turns out that the Shiraz selection is well regarded.  Tastings are inexpensive at R40 to R60 per person for 4 wines.  And for golfers, there is a chipping competition on the last Friday and Saturday of each month.

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Views across the Helderberg Mountains from the Ernie Els Winery terrace © The Whistletrip

Next was the world famous Delaire Graff Estate – worth every bit of its reputation as a holistically stellar wine and food experience.  Diamond jeweler Laurence Graff bought the Delaire estate in 2003 and 6 years later opened its gates to reveal a Relais & Chateaux hotel with exquisite restaurant and gardens.

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Views from the Delaire Graff © The Whistletrip

The modern classic aesthetic incorporates incredible contemporary art and the grand but welcoming Wine Lounge opens up onto a terrace with gorgeous views over the Stellenbosch Valley.

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Brilliantly showcased modern art at Delaire Graff © The Whistletrip

Tastings can be paired with cheese or chocolates and are terrific value at R30 for 3 wines.  Visitors are welcome to roam the vines on the estate’s quiet slopes and to admire the botanical diversity in the winding gardens.

By now having had my fill of wine, we headed to Franschhoek – a must-see tiny town about 30 minutes from Stellenbosch.  Adorable white-washed Cape Dutch homesteads sit in the Franschhoek Valley.  Main street is lined with eclectic galleries and boutiques:  I browsed my way through the Moór Gallery, The Armchair Explorer bookstore with early edition tomes on African and European military history, and Avoova‘s collection of elegant black and white crafts made from ostrich eggs.

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19th century Dutch Reformed Church is a lovely example of the whitewashed buildings in the Franschhoek Valley © The Whistletrip

The grand finale was a visit to the outstanding – do not missBabylonstoren.  Eight acres of working fruit and vegetable gardens with pathways charmingly covered in peach pips, two renowned restaurants (Babel and Greenhouse) using products grown on this old farm, and a cozy bakery, cold meats and cheese store onsite from which to make a picnic.  There is a hotel with spa on location, both of which are highly regarded.

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Map of Babylonstoren outlines the range of gardens, home produce stores, restaurants and winery on offer © Babylonstoren
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The working gardens of Babylonstoren © The Whistletrip
  • Wish I had:  Suppered in Franschhoek.  It has some of South Africa’s best restaurants – The Tasting Room at Le Quartier Français or The Kitchen at Maison.  Helpful guides to the best in local food include EatOut.

Day 3:  Cape of Good Hope & Table Mountain Hike

Naz met me bright and early to make sure that we beat the crowds to wonderful Boulders Beach.  African penguins cover this spectacular sandy beach, and huddle between the majestic granite rocks.  These lovely birds even nestle beneath the wooden pedestrian walkway so that you can see their feathers and pruning right up close.

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Adorable penguins on Boulder Beach © The Whistletrip

Hard though it was to leave the penguins behind, we drove on to Cape Point nature reserve to meander up trails with sweeping views across not one ocean, but both the Atlantic and Indian Oceans.  Set aside an least an hour to enjoy the walk unrushed and to make your way to the Cape Point sign marking the most south western point of the African continent.

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Views through Cape Point reserve © The Whistletrip

To reach Kirstenbosch Gardens, we took Chapman’s Peak Drive – the gorgeous cliffside route bringing you to look over Hout Bay, where stunning blue waters meet vegetation covered rocks.  It was tempting to stop a while in the town of Hout Bay, but I was thrilled not to miss the amazing botanical gardens at the foot of Table Mountain.  Be sure to enjoy the elevated walk through the tree line, from which you both peer down over the plants and ponds, and up towards announced the spectacular sandstone.

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From Chapman’s Peak Drive looking out to Hout Bay © The Whistletrip

With Table Mountain finally open, we headed to Platteklip Gorge, the trail that starts close to the lower cable station.  The gorge is the most direct route to the top, and the hike normally takes one to three hours.  Carry water, wear hats, and slather on sunscreen since most of the trail is exposed. A few segments are quite steep but should be fine for someone of average fitness. In fact I was overtaken by a local lady in her 30s carrying her months old baby as she clambered up the trail like a mountain goat.  Inspiration.

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A way still to go up on Platteklip Gorge © The Whistletrip

Views back over the city and Table Bay keep you pushing upwards for more.  Once at the top, of Table Mountain is bustling.  Paved walkways make it easy to explore for visitors who need to take the cable car up.  It is absolutely possible to hike to the top and buy a one-way cable car ticket down. From here back to the Cape Grace to prepare for the next leg of the journey:  safari.

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At the top of Table Mountain © The Whistletrip
  • Shop:  For South African designed sculptures in handsome dark stone, head to Red Hill Village in Cape Point.   Exploring the labyrinthine outdoor display of striking pieces is such a memorable experience, and there is no better place to find a unique souvenir.  You need time to haggle and paying in US$ guarantees the best prices.

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    Red Hill Village has amazing fields of sculptures for sale © The Whistletrip
  • Cocktail:   Enjoy sundowners at the top of Table Mountain.  The café beside the upper cable car station serves good quality wine and beer.

Next:  Sabi Sand & Kruger National Park:  4 Nights on South African Safari