We’ve decided it’s best to head south next February, and where better than the Cape, which offers the unique combination of mountainous scenery, sunshine, beautiful 17th/18th-century villages and vineyards, world-class wine and… penguins?
The Cape also lies in the same time zone, so no jet lag. We will be staying for four nights in Cape Town at the Winchester Mansions Hotel overlooking the Atlantic and four nights at the Franschhoek Country House, a boutique hotel in pretty Franschhoek. Both have swimming pools.
We’ve hired The Cape Town Tour Guide Company to manage and escort the entire tour, providing all the transport, tastings, and entrances on this very comprehensive trip so that we can all feel secure. They’ve also chosen terrific restaurants, while Henry Jeffreys, the award-winning author of Empire of Booze and co-presenter of the podcast series Intoxicating History, has chosen all the vineyards.
As Craig Brown says, 'Henry Jeffreys is everything you want a wine writer to be: funny, knowing, unpretentious but also un-blokeish, funny, clever, refreshing, original, funny, and inquisitive. And did I say funny?’ The Oldie publisher James Pembroke and Amelia Milne will also be accompanying the tour.
Henry writes:
'The Cape is not only perhaps the most beautiful wine region in the world; it’s also one of the most historic: the Klein Constantia estate dates to 1685. On this trip we’ll be tasting its legendary sweet wine beloved of Napoleon as well as superb cabernet sauvignon, chenin blanc, and fizz from Stellenbosch, pinot noir, and chardonnay to rival the best of Burgundy from Hemel-en-Aarde (heaven and earth) Valley and wild Rhône-inspired reds from Swartland. And all packaged with incredible scenery, beautiful gardens, and delicious food. I can’t wait.'
ITINERARY
Day 1: Wednesday 17th February – Arrive in Cape Town
Flight BA45 departs London Heathrow at 20:40 and arrives in Cape Town at 10:20 the next day.
Day 2: 18th February – Arrival from London and a braai with Mandela’s guard
10:20 Meet and greet at Cape Town airport and transfer to the Winchester Mansions Hotel in Sea Point, which overlooks the Atlantic.
After lunch and a relaxing afternoon by the pool, depart for a braai experience at the home of renowned artist Beezy Bailey near the Mount Nelson hotel. Once the embers are ready, enjoy a generous selection of traditional South African braaied meats – boerewors, lamb chops, chicken, and steak – served with fresh salads, pap and garlic bread. The evening ends with a classic South African dessert.
Joining us will be Christo Brand, who was one of the prison warders assigned to guard Nelson Mandela on Robben Island from 1978. Over time, a remarkable friendship developed between them. Brand later shared his experiences in the memoir Doing Life with Mandela, offering a unique perspective on Mandela’s character and humanity.
Day 3: Friday 19th February – Table Mountain and Robben Island
We visit the new and old city as we experience the various cultures and architectural designs associated with this historical city. A trip by cable car up Table Mountain (skip the queue tickets) will present a spectacular aerial perspective. We will discover the history of European settlement in South Africa since 1652, which includes indigenous, Dutch, and British settlements. We will also walk through Company's Gardens, which began life in the 17th century.
After a simple lunch at a local coffee shop, we depart for Robben Island, which is situated just a few kilometres offshore. Nelson Mandela was incarcerated here for almost 20 years. The intention to silence anti-apartheid leaders by imprisoning them on Robben Island had the opposite effect, and the island became a focal point for international resistance to the apartheid regime. Today it has become a symbol of freedom, the transformative power of forgiveness and a place of political pilgrimage. The entire island is now a UN World Heritage Site. Dinner at The Codfather in Camps Bay.
Day 4: Saturday 20th February – Kirstenbosch Gardens, Klein Constantia, and sunset boat cruise
Morning visit to Kirstenbosch National Botanical Garden, which is one of the world’s most celebrated botanical gardens, showcasing the extraordinary diversity of South Africa’s indigenous flora. Established in 1913 to protect the unique Cape Floral Kingdom, the garden is home to vibrant proteas, ancient cycads, and seasonal wildflowers.
We will then have lunch and a wine-tasting at Klein Constantia, world-renowned for its iconic sweet wine, Vin de Constance, once enjoyed by European royalty and Napoleon Bonaparte. Today, Klein Constantia produces elegant cool-climate wines and offers breathtaking vineyard views just minutes from central Cape Town.
End the day with a sunset boat cruise at the V&A Waterfront, followed by dinner at Marble at the Waterfront.
Day 5: Sunday 21st February – Tour of the Cape Peninsula and Boulders Beach Penguin Tour
Today we experience some of the most spectacular views in the world. Typically we like to include activities such as travelling along Chapman’s Peak Drive, one of the country’s most famous scenic drives; viewing ostriches, taking a walk through the Cape of Good Hope Nature Reserve, viewing the historical lighthouses, and, of course, the highlight of the day is the view site at Cape Point itself. This is an incredibly beautiful mass of land that dramatically juts out into the ocean.
One cannot help but imagine the 15th-century Portuguese sailors who would travel for months in their attempts to round the Cape and get to India.
From Cape Point, we make our way back along False Bay to Simon’s Town to view the African penguins at Boulders Beach. Dinner at Table Seven.
Day 6: Monday 22nd February – Cape Winelands Tour – Stellenbosch
Today, we leave the Winchester Mansions Hotel for Franschhoek Country House, in pretty Franschhoek. (https://fch.co.za) Franschhoek is known as South Africa’s 'French Corner’. Settled by French Huguenots in the 17th century, it blends rich history with world-class wine estates, gourmet restaurants, and boutique galleries. Surrounded by vineyards and mountains, Franschhoek offers a charming village atmosphere and is a favourite stop for food and wine lovers visiting the Western Cape.
En route, we have a wine tasting at Vergelegen Wine Estate, followed by lunch and wine tasting at the stunning Delaire Graff Estate described by an Oldie staff member as ‘unmissable'. Check in at Franschhoek Country House followed by dinner at Grande Provence.
Day 7: Tuesday 23rd February – Cape Winelands Tour – Franschhoek.
Tour of Franschhoek, including wine tasting at The Studio at Leeu Estate of Mullineux & Leeu Family Wines, followed by lunch at The French Connection Bistro. After lunch, we visit the gardens at Babylonstoren, have a wine-tasting there and visit the scent room and farm shops. Dinner at Monneaux Restaurant.
Day 8: Wednesday 24th February – Travel over the mountain and explore the Overberg
This morning, we travel over the scenic Franschhoek Pass and on to Hermanus through the Heaven and Earth Valley, which is a breathtaking wine region of rolling vineyards, mountain backdrops, and fynbos-covered hills. Renowned for cool-climate Pinot Noir and Chardonnay, it offers scenic drives, boutique wine estates, and bucolic views.
Wine tasting at Bouchard Finlayson, a collaboration between a Burgundian winemaker, Paul Bouchard, and a local, Peter Finlayson, making French-inspired wines. After lunch, we have a bubbly tasting at La Vierge followed by a wine tasting at Hamilton Russel Vineyards, which was founded by Tim Hamilton Russell in 1975, who is the pioneer of Pinot Noir in one of the coolest parts of the cape. It is still in family hands. Return home and take a short walk to an early dinner at Bientangs Cave in Hermanus.
Day 9: Thursday 25th February – Cape Winelands continued – Stellenbosch and Paarl
This morning, we visit the town of Stellenbosch for a tour of the town. Stellenbosch is one of South Africa’s oldest and most picturesque towns, set among the vineyards and mountains of the Cape Winelands just outside Cape Town. Founded in 1679, it is famous for its oak-lined streets, Cape Dutch architecture, and lively university atmosphere. Art galleries, cafés, and boutique shops line the historic centre, while surrounding wine estates produce some of the country’s finest vintages. Visitors enjoy strolling shaded avenues, tasting wines, and soaking up the town’s relaxed heritage charm and beauty.
We travel for lunch and a wine tasting at Tokara Wine Estate in the foothills of the Simonsberg mountain. Founded in 1994 by billionaire GT Ferreira, as well as their own wines, they also produce olive oil and have the most beautiful gardens and art.
Afterwards, we travel to Paarl for a wine tasting at Brookdale, an ambitious estate run by Englishman Tim Rudd, who produces unusual varieties like Picpoul and has some of the oldest Chenin Blanc vineyards in the Cape before returning to Franschhoek.
Transfer to the famous La Petite Ferme for the quiz and a farewell dinner.
Day 10: Friday 26 February – Swartland wine experience and departure
09:00 depart for the scenic Swartland region, an area known for its rugged beauty, wheat fields, and a new generation of innovative winemakers. Wine tasting at AA Badenhorst Family Wines, one of the pioneering estates of the Swartland wine movement. Enjoy a relaxed tasting of their characterful, terroir-driven wines at the historic Kalmoesfontein farm.
Continue through the rolling countryside to the charming village of Riebeek Kasteel. After lunch, wine tasting at Kloovenburg Wine Estate, a historic family-run farm known for its excellent wines and olives.
Afterwards, enjoy a gentle stroll through the village of Riebeek-Kasteel, browsing its small galleries, cafés, and artisan shops before departing for Cape Town International Airport. Depart on Flight BA42 at 20:50 from Cape Town, arriving at London Heathrow Airport at 07:00 at the next day (Saturday, 27th February).
PRICES AND HOW TO BOOK:
Call 01225 427311 or please email Katherine at reservations@theoldie.co.uk
Price per person sharing a double/twin room: £4,795 including eight nights’ accommodation, all meals, all transport (including to Robben Island), the sunset harbour cruise and all entrances/tastings – everything apart from the return flights and drinks outside of meals.
Single supplement: £900; non-refundable deposit of £750 per person; balance due 1st November 2026.
BA are offering return flights for around £1,100 return.
