Tailor-made Holiday · South Africa
South African Garden Route and Safari
Tailor-made, always
Every trip built from scratch around your dates, pace and preferences.
Your own specialist
One named person and a 24-hour number while you travel.
Hundreds of five-star reviews
Rated Excellent on Trustpilot across ten years of LGBTQ+ luxury travel.
At a glance
This is truly a bucket list itinerary. Embark on a captivating South African odyssey that blends the dynamic allure of Cape Town, the lush vineyards of the Winelands, the breathtaking beauty of the Garden Route, and the unparalleled thrill of a safari in world-renowned game reserves.
This comprehensive itinerary is designed to immerse you in the very best of South Africa, inviting you to experience the awe-inspiring Table Mountain, delve into the rich history of Robben Island, and indulge in the exquisite wines that make South Africa a connoisseur's paradise.
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Journey to Plettenberg Bay, known as Africa's most stunning beach destination, for an idyllic escape that epitomizes coastal luxury. The pinnacle of your adventure awaits at either Kwandwe or Amakhala Game Reserve, both offering a safari experience that promises close encounters with Africa's most iconic wildlife.
As your journey unfolds, each day in South Africa brings new delights and discoveries. From the vibrant streets of Cape Town to the serene landscapes of the Winelands, every moment is an invitation to immerse yourself in the country's rich tapestry. This itinerary is not just a trip; it's a journey of a lifetime, meticulously designed to connect you with the soul of South Africa.
This journey, curated for the discerning traveler, is a tapestry of unique experiences, blending adventure with luxury, and creating memories that last a lifetime. As with all of our itineraries, it can also be adapted to suit your travel dreams - just speak to one of our luxury travel experts to start planning today.

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 to 3: Cape Town
Upon arrival, pick up your hire car and head to your Cape Town hotel. You’ll spend three days in Cape Town exploring the beauty and history of the city.
Places such as Table Mountain, Robben Island and the Cape of Good Hope are all easily reachable and are well worth spending time at.
Cape Town is by far the continent’s most gay-friendly destination with a number of great venues and if you’re planning a wedding then it’s also a beautiful destination.
Day 4 to 6: South Africa's Winelands
Today you’ll drive into the winelands, about 40 minutes from Cape Town to the 5* Grande Roche Hotel where you’ll stay in a Studio Suite. Your stay includes sparkling wine and an Oyster breakfast.
Nestled at the foot of the magnificent Paarl Rock Mountain, the boutique hotel is where history interacts with modern day comforts and the gentle rhythm of a working fruit and wine farm creates a peaceful escape for rest and relaxation. A proud member of Small Luxury Hotels of the World, featuring 28 elegant suites you will experience comfort and tranquility, personal service and meticulous attention to detail.
With breathtaking views across the Paarl Wine Valley, Grande Roche Hotel offers guests the perfect setting for a Winelands escape. Award-winning Bosman’s Restaurant offers all year dining with fireplaces for winter and an outside terrace overlooking the vineyards for summer evenings. Michelin trained Chefs infuse classic South African dishes with international cuisine and the in-house Sommelier is able to recommend wines from the list of 400 labels.
The boutique choice is The Last Word Franschhoek, an exclusive 5-star historic residence in the heart of the Franschhoek village, the gourmet capital of South Africa. The hotel is just a minute’s walk from excellent award-winning restaurants and numerous character-filled boutique style shops and art galleries.
The Franschhoek valley offers world-class wine estates, tastings and cellar tours nestled between towering mountains and beautiful vineyards and the picturesque French village hosts some of the best cuisine from internationally recognised gourmet chefs. The valley is also the idyllic setting for walking trails, hiking, cycling, bird watching, horse riding, fly-fishing and golf.
Whilst you’re there the hotel can arrange a host of luxury escapes including horseback wine tours, gourmet dining at some of South Africa’s top restaurants, exploring the region’s French heritage – unforgettable memories are waiting to be made.
Day 7: Oudtshoorn
Today you’ll continue along the garden route by driving to Oudtshoorn, the ostrich capital of the world and site of the Cango Coves, an underground network of limestone tunnels and chambers
You’ll stay at the Rosenhof Country House, where you are able to enjoy traditional country cuisine complemented by an extensive wine list. There is a fully equipped gym and sauna and with its luxurious facilities and excellent service, Rosenhof is recognized as one of the finest establishments in the region.
The boutique choice is Hlangana Lodge, one of the finest small luxury establishments in South Africa. Every room has a private veranda overlooking the exotic gardens and saltwater swimming pool.
Day 8 to 11: Plettenberg Bay
You’ll drive to the beautiful Plettenberg Bay.
Situated on a rocky headland in Africa’s most spectacular beach town of Plettenberg Bay is the ultimate escape, The Plettenberg. This owner-managed property showcases the most breathtaking vistas in Southern Africa with views of the ocean, mountains and endless stretches of golden beach. Located in the heart of South Africa’s elite favorite seaside vacation spot and Garden Route, world-renowned for its excellent outdoor activities. It is the ideal place to both relax and unwind or recharge and reinvigorate. At The Plettenberg the charming service and the setting combine to create the ultimate story, one of a South African seaside experience unlike any other.
At our boutique option, the Hog Hollow, you’ll find outstanding cuisine, personalized accommodation & hospitality. With just 16 rooms all with private wooden decks, king-sized beds, most with cosy fireplaces. Breakfast & dinner served on the boma deck or around the communal candle-lit dining table.
Spend a few nights here soaking up the coastal atmosphere and relaxing.
Day 11 to 13: Safari and game viewing
Spend three nights at one of our recommended game lodges. All your meals are included as well as safari activities.
At the 5* Kwandwe Ecca Lodge you’ll find a vast wilderness flanking the banks of the Great Fish River in South Africa’s Eastern Cape region. Home to a diverse array of wildlife including the ‘Big Five’, as well as cheetah, hippo, springbok, giraffe and more. The soul-stirring beauty of the landscape lends its charm to all four of its modern, yet intimate lodges and villas, all Relais & Chateaux accredited. A delight to travellers young and old the reserve provides superb game and bird viewing as well as providing habitat for protected species such as the Black Rhino and Blue Crane.
Some days you’ll take a safari vehicle and the next a boat cruise. Other activities on the reserve include bush and big game walks, boat cruise, fishing, massages, rhino monitoring, rhino darting and bush banqueting.
For our boutique option, you’ll find Hlosi Game Lodge a 5-star Eastern Cape lodge in the Amakhala reserve. Lying along a curve of hill above the Bushman’s River plain in the Eastern Cape, the luxury game lodge is a quiet, grassland retreat offering a rich and intimate luxury African safari experience. As part of the 7000-hectare Amakhala game reserve, Hlosi provides a rich, informative luxury experience. This intimate lodge redefines exclusivity with four individually styled twin/double suites designed to capture the spirit of a bygone era, while providing the luxuries of contemporary lodge living.
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.
One named specialist, first enquiry to homecoming. No call centre, and nothing is charged until you decide to book.