Tailor-made Holiday · South Africa
South Africa Food & Wine Tour in the Winelands
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Every trip built from scratch around your dates, pace and preferences.
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At a glance
From the cosmopolitan energy of Cape Town to the rolling vineyards of Franschhoek and the untamed wilderness of Sabi Sands, this journey blends culture, cuisine, and safari adventure. Walk through history, indulge in world-class dining, sip award-winning wines, and witness Africa’s most iconic wildlife in their natural habitat—an unforgettable experience of luxury and discovery.
Cape Town welcomes you with stunning landscapes and deep history. Stroll through Bo-Kaap’s colorful streets, learning about its Cape Malay heritage, and take a foodie’s journey through the city’s diverse flavors. Ride the Table Mountain cable car for breathtaking views, then explore the profound legacy of Nelson Mandela on Robben Island. Evenings are for indulgence, with Michelin-worthy dining and sumptuous wines at the city’s finest restaurants.
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Venture into the Cape Winelands, where Franschhoek’s vineyards and mountain-framed estates invite you to slow down and savor the moment. At Babylonstoren, stroll through fruit orchards, sip wines straight from the barrel, and embrace the simple elegance of farm-to-table living. But soon, the call of the wild takes you to Sabi Sands, where lions, leopards, and elephants roam freely. Game drives led by expert trackers reveal Africa’s most spectacular wildlife, while sunset drinks in the bush make for moments of pure magic.
As the sun rises over Sabi Sands, your final morning brings one last safari adventure. The journey may end, but the memories—of golden savannahs, whispered histories, and the thrill of the wild—will stay with you forever.
Day by day
This is a sample plan, not a fixed departure. Days can be added, removed or reordered, and almost every client changes something. Prices are an entry-level guide; your quote will be exact.
Day 1: Arrival in Cape Town & Culinary Delights
Arrive in Cape Town, where a warm welcome awaits at the airport before your private transfer to the iconic Belmond Mount Nelson. Nestled at the foot of Table Mountain, this legendary pink-hued hotel is a sanctuary of elegance and charm. Here, dining is more than a meal—it’s an art form. Indulge in an exquisite afternoon tea accompanied by live piano melodies, savor pan-Asian flavors at The Red Room, or enjoy Cape Malay specialties in the tranquil gardens. This is not just a stay; it’s a culinary journey that sets the tone for an extraordinary South African adventure.
Day 2: A Taste of Cape Town & Table Mountain
Immerse yourself in Cape Town’s history through its food on a guided walking tour through the city’s streets. Sample traditional bunny chow, bobotie, and Muslim rose milkshake, stopping at artisanal coffee shops and vibrant markets. This is more than a meal—it’s a deep dive into the city’s multicultural heritage. Afterward, ascend Table Mountain by cable car, watching as the city unfolds beneath you in breathtaking clarity. As the mist lifts, enjoy unparalleled views of the Mother City, the perfect way to conclude a day of discovery before retreating to the comfort of Mount Nelson.
Day 3: The Story of Mandela & Robben Island
Step into South Africa’s past with a walking tour tracing Nelson Mandela’s secret negotiations in Cape Town that led to his release. Then, set sail for Robben Island, where former political prisoners share first-hand accounts of life behind bars. The experience is profound, offering insight into the country’s painful yet powerful journey to freedom. In the evening, Cape Town’s world-class dining scene awaits. With reservations at a top restaurant such as La Colombe, Nobu, or FYN, your night is one of gastronomic brilliance, paired with award-winning South African wines.
Day 4: Exploring Bo-Kaap & Cape Town’s Coast
Stroll the vibrant streets of Bo-Kaap, where brightly colored homes and the aroma of Cape Malay spices tell the story of this historic neighborhood. Led by a local expert, discover the area’s fascinating history before stepping into a traditional kitchen for an interactive cooking class, preparing and savoring authentic dishes. Later, unwind on the golden sands of Camps Bay, where the waves of the Atlantic meet the dramatic backdrop of the Twelve Apostles Mountain Range, offering the perfect place to soak up the relaxed energy of Cape Town.
Day 5: Cape Peninsula & Boulders Beach Penguins
Embark on a spectacular scenic drive along Chapman’s Peak, winding along dramatic cliffs to reach the Cape of Good Hope. Feel the power of the oceans where the Atlantic and Indian currents converge. Visit Boulders Beach, where a colony of African penguins waddle along the shore. A leisurely lunch in the historic naval town of Simon’s Town follows before ending the day at Kirstenbosch Botanical Gardens, a lush paradise of indigenous flora. This day is a love letter to South Africa’s natural beauty.
Day 6: Into the Cape Winelands
Leave the city behind and journey into Stellenbosch and Franschhoek, two of the world’s most celebrated wine regions. Enjoy private wine tastings at award-winning estates, soaking in the scenic landscapes of rolling vineyards and Cape Dutch architecture. In Franschhoek, the Gourmet Capital of South Africa, indulge in Michelin-worthy cuisine paired with the region’s finest vintages. Check into Babylonstoren, a luxurious working farm retreat, where farm-to-table dining, exquisite gardens, and vineyard views offer an idyllic escape into wine country bliss.
Day 7: Behind the Scenes in the Winelands
Today is about more than wine. Explore boutique farms, discover organic winemaking techniques, and take a behind-the-scenes look at historic cellars. Stroll through lush vineyards, visit art galleries in Stellenbosch, or simply savor handcrafted wines and farm-fresh delicacies with spectacular views. Whether it’s olive oil tastings, vineyard picnics, or private barrel tastings, your day is completely tailored to your tastes. As the sun sets, Franschhoek’s world-class restaurants await, offering another evening of culinary enchantment.
Day 8: Slow Living at Babylonstoren
Wake up to the rhythm of farm life at Babylonstoren, where guests can stroll through fruit orchards, flower gardens, and vineyards. Join a guided tour through the estate’s wine cellar, row across the farm’s tranquil dam, or simply unwind with a spa treatment. This day is about savoring the moment, embracing the beauty of nature, and indulging in fresh, seasonal cuisine. The evening invites you to another gastronomic adventure, with reservations at one of Franschhoek’s acclaimed restaurants, such as La Petite Colombe or Babel.
Day 9: From Vineyards to the Wild
Bid farewell to the Cape Winelands and board a flight to Skukuza, the gateway to South Africa’s premier safari destination—Sabi Sands Private Game Reserve. Arriving at Ulusaba Safari Lodge, the adventure begins with your first afternoon game drive. Led by expert rangers and trackers, venture into the untamed wilderness, where lions roar, leopards stalk, and elephants graze along the riverbanks. As the sun sets, return to the lodge for dinner under the stars, where the magic of the African bush comes alive.
Day 10: Big Five Safari & Sundowners
At Ulusaba, safari is a deeply immersive experience. Begin the day with a sunrise game drive, witnessing the bush come to life. Spot the Big Five, track rare black and white rhinos, and marvel at a herd of elephants in the morning light. Between drives, relax at the lodge, enjoy a wine tasting, or indulge in pan-African cuisine. The afternoon brings another thrilling game drive, concluding with sundowners in the open plains, where the golden light transforms the landscape into pure safari magic.
Day 11: The Wild Heart of Sabi Sands
The rhythm of safari life continues with an early morning game drive, a time when predators are on the prowl and nocturnal creatures retreat. Watch in awe as a leopard slinks through the brush or a pride of lions prepares for a hunt. The afternoon offers another chance to explore the reserve, perhaps encountering the rare and endangered African wild dog. As night falls, the sounds of the bush surround you, a reminder that this landscape is raw, untamed, and breathtakingly beautiful.
Day 12: Farewell to the Wild
As the sun rises over Sabi Sands, take one last game drive before your private transfer to Skukuza Airport. A scenic flight to Johannesburg marks the end of your journey, but the memories of South Africa’s landscapes, flavors, and wildlife will remain with you forever.
Our Experts
There's no better way to appreciate the natural world than by taking part in a South African safari. You'll have the chance to see the Big Five whilst never compromising when it comes to luxury.
The cosmopolitan hub of Cape Town is often overlooked as a fantastic travel destination. It has a palpably vibrant character and a flourishing food scene. I'd recommend it to anyone wanting to experience something completely different.
Stellar service. Stellar products. Stellar people and it gets so much better when you pick up the phone and call.
Anthony S.
Super client centred service. From first contact I have had warm, efficient, friendly and flexible service.
John
I’m confident in giving Out Of Office a 5-star review! They are one of the leaders in this space without a doubt.
Tiberiu
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Frequently asked questions
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specialising in tailor-made holidays and extraordinary journeys around the world. We create bespoke luxury holidays, LGBTQ+ honeymoons, safaris, cruises, beach escapes, private tours and group trips, with every itinerary designed around you. Our travel specialists combine global expertise, first-hand destination knowledge and trusted local partners to create seamless, highly personalised experiences.
Is Out Of Office a gay travel agency?
Out Of Office is an LGBTQ+ owned and run luxury travel specialist, with particular expertise in gay and LGBTQ+ travel. We understand the additional considerations that can come with travelling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveller, including friends, families and allies. Many of our clients are not members of the LGBTQ+ community, but choose Out Of Office for our luxury travel expertise, personalised service and discretion.
Do you create tailor-made LGBTQ+ holidays?
Yes. Every tailor-made trip with Out Of Office is designed from scratch around your interests, travel style, budget and the way you want to experience a destination. We can arrange luxury hotels, private transfers, flights, guides, excursions, cruises and special experiences as part of one personalised itinerary. The journeys shown on our website are there to inspire you rather than restrict you; only clearly identified group departures operate as fixed itineraries.
How do you choose LGBTQ+ friendly hotels and destinations?
We combine first-hand destination knowledge with trusted local expertise to recommend luxury hotels, resorts and experiences where LGBTQ+ travellers can feel informed and welcome. We also consider the laws, customs and attitudes of each destination, because LGBTQ+ rights and experiences differ around the world. Our team regularly visit many of the properties we work with and where a destination requires greater awareness, we give you clear and considered advice so that you can make an informed decision about where and how you travel.
We plant trees for every booking
For every booking made with Out Of Office we commit to planting trees in your name to help reduce the impact of travel on future generations. You'll even get a link to see where your trees are planted in the world via our partner Ecologi.
We donate to Rainbow Railroad with every booking
Rainbow Railroad helps LGBTQ+ people escape state-sponsored violence and persecution. A donation goes with every trip we sell, funded by us and never added to your price.
Start Planning Your Trip
Tell us where you would love to go, when you are thinking of travelling and what kind of trip you have in mind. One of our LGBTQ+ travel specialists will create a tailor-made itinerary designed around your destination, style and preferences.
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