MAY 2027
Day 1 – Saturday 22:Â Welcome to Cape Town
Welcome to Cape Town! You’ll be met in the arrivals hall with a VIP meet-and-greet, whisked through the airport formalities and driven to your hotel, the stylish Canopy by Hilton on Kloof Street, your home for the next three nights. Settle in and enjoy the late afternoon at leisure.
This evening your South African adventure begins in style. We gather for welcome drinks on the rooftop of The Silo, the landmark hotel perched above the V&A Waterfront, before being escorted to the Wisdom Room for a beautiful food-and-wine paired private welcome dinner. There’s no better place to raise a first glass together!
Stay: Canopy by Hilton Cape Town Longkloof
Meals included:Â Dinner
Day 2 – Sunday 23:Â Constantia & the Cape Peninsula
After breakfast we set off for the Constantia Wine Route, the oldest wine-growing corner of the Cape, with more than three centuries of winemaking behind it — and, wonderfully, a growing number of women now at the helm of its estates. It’s a lovely full-circle moment when you remember that the very first person to own land here was a woman: Catharina Ras, granted the farm now known as Steenberg back in 1682.
At Steenberg we’re welcomed by Carryn Wiltshire and Simone Haikney for an executive tasting in the private cellar, where you’ll sip the estate’s celebrated 1682 Pinot Noir Cap Classique alongside a flight of flagship wines. From there we cross Ou Kaapse Weg towards Cape Point to meet Roushana and her team for something truly special: a Veld & Sea wild food experience. Across five courses you’ll taste the season itself — herbs gathered from the mountainside, seaweed foraged from the coast, edible flowers picked from the garden — all paired with local wines and wild sodas, while the foragers and chef share the story behind every dish.
If time allows, we’ll slip away to a quiet beach to visit an African penguin colony, well away from the crowds, before making our way back along the spectacular Chapman’s Peak Drive. Then the evening is yours – we’ll happily point you towards the Time Out Market at the Waterfront, where fourteen kitchens from some of the city’s best chefs sit under one roof.
Stay:Canopy by Hilton Cape Town Longkloof
Meals included:Â Breakfast, Lunch
Day 3 – Monday 24:Â Exploring Beautiful Cape Town
You may want to keep breakfast light this morning, because you’ll be eating your way through Cape Town before the day is done! We begin at the top, ascending Table Mountain by cable car (weather permitting) to take in those famous views from every vantage point. At the summit we toast the city below with a glass of superior Cap Classique, chosen for us by Caroline of Caroline’s Fine Wines.
Back down in the heart of the city, we meet our specialist guide for a walking journey told entirely through food and drink. This is Cape Town seen through her flavours and her people: traditional treats, artisan producers, local wines and the stories behind them, with plenty to taste at every stop. This is lunch for the day, and then some.
Tonight we dine at FYN, one of the most celebrated restaurants on the continent and a regular on The World’s 50 Best Restaurants list, for a food and wine pairing that lingers long in the memory.
Stay:Canopy by Hilton Cape Town Longkloof
Meals included:Â Breakfast, Lunch, Dinner
Day 4 -Tuesday 25:Â Sculpture, Hemel-en-Aarde and Franschhoek
This morning we check out and set off for the Cape Winelands, a short and beautiful drive from the city. Our first stop is the Dylan Lewis Sculpture Garden near Stellenbosch, where more than sixty of the artist’s bronzes are set along kilometres of paths winding through indigenous fynbos – a wild, contemplative kind of beauty.
We carry on over the mountains into the Hemel-en-Aarde Valley, one of South Africa’s great cool-climate regions. At Hamilton Russell Vineyards we’re hosted by Talita Engelbrecht, alongside Berene Sauls of Tesselaarsdal – whose own label is one of the most heart-warming stories in South African wine – for a tasting and a relaxed farm-style lunch. In the afternoon we visit Hasher Family Estate to meet winemaker Natasha Williams, the talent behind her own label, Lelie van Saron.
Tonight we check into the stunning Mont Rochelle, our home for the next four nights, and dine in-house at MIKO.
Stay: Mont Rochelle, Franschhoek
Meals included:Â Breakfast, Lunch, Dinner
Day 5 – Wednesday 26: Your Day to Explore Franschhoek
A gentler day, and a welcome one. Franschhoek is a sleepy, gorgeous little town made for meandering. Wander the main street, browse the galleries, book a treatment at the spa, or simply do nothing at all with a glass in hand. In the evening we head out together for a late dinner at Protégé, where refined, flavour-packed cooking meets an easy, unfussy kind of fine dining.
Stay: Mont Rochelle, Franschhoek
Meals included:Â Breakfast, Dinner
Day 6 – Thursday 27:Â Cape Winelands & Diamonds
Today is the one the name of this tour promises. We start at Bartinney Estate with winemaker Ronell Wiid for a Cape Fynbos and Wine tasting – a multi-sensory experience that changes the way you taste, and a lovely nod to the estate’s work conserving the Cape’s extraordinary biodiversity.
A short drive brings us to Delaire Graff, the Jewel of the Cape Winelands. Two estate ambassadors will walk you through gardens in permanent bloom, past sculptures and works from Laurence Graff’s personal collection of South Africa’s finest contemporary artists. There’s time to step inside the Graff boutique – Africa’s first – where the diamonds are every bit as dazzling as the setting. Then a tutored tasting on the terrace, wrapped in mountain views, with platters of local cheese and charcuterie.
In complete contrast, the afternoon takes us to Stellekaya, a boutique cellar right in the middle of Stellenbosch, to meet Jane Lello and Rose Kruger and taste the noble red varietals they do so well.
Dinner tonight is at Chefs Warehouse at Maison, a relaxed, contemporary Winelands table with all the warmth of an old friend who happens to cook beautifully.
Stay: Mont Rochelle, Franschhoek
Meals included:Â Breakfast, Lunch, Dinner
Day 7 – Friday 28:Â More of the Delicious Cape Winelands
A leisurely start, then off to Jordan Wines near Stellenbosch for a guided walk through the cellar and the winemaking, followed by a picnic lunch out among the vines. From there we visit Mitre’s Edge to meet winemaker Lola Nicholls, whose family-run boutique winery has focused on red wines and Bordeaux-style blends since the late nineties.
Our final night in the Winelands is a memorable one. We dine at Rust en Vrede, set in the estate’s original cellar – now a historic monument turned elegant dining room – for one of the great wine-paired dinners in the Cape.
Stay: Mont Rochelle, Franschhoek
Meals included:Â Breakfast, Lunch, Dinner
Days 8 to 10 – Saturday 29 to Monday 31: Safari Time
After breakfast we say goodbye to the Winelands and fly from Cape Town to Gqeberha (formerly Port Elizabeth), where we’re met and driven out to Kariega Private Game Reserve. Here, at the beautifully secluded luxury camp Settlers Drift, the pace changes entirely.
Your days settle into the wonderful rhythm of safari. Early coffee before a morning game drive, when the animals are at their most active, with a refreshment stop out in the bush. Back to the lodge for breakfast and a lazy midday siesta, or a nature walk if you’re feeling active. Afternoon tea, then out again for the senset drive and that great safari ritual: sundowners in hand as the light turns golden. Evenings are spent together over dinner, swapping the day’s sightings, sometimes around an open-air boma fire.
Everything here is included – all your meals, selected beverages, your game drives and activities. Three nights simply to be present in the wild and experience the true Africa.
Stay: Kariega Settlers Drift (fully inclusive of all meals and snacks)
Meals included: Fully inclusive of all meals and snacks
JUNE 2027
Day 11 – Tuesday 01:Â Homeward bound
One last morning game drive and breakfast before we check out and make our way back to the airport for the flight to Cape Town. From here you’ll either connect to your international flight home, or carry on with your own South African plans. Whatever comes next, you’ll leave with a heart full of memories, a new circle of wine-loving friends, and a serious love for South Africa.
Bon voyage!
