Winelands
Winelands Travel Guides
Written by the specialists who plan our trips to Winelands: where to go, when, and what is worth knowing before you book.
All Winelands Travel Guides
The Best Luxury Experiences in South Africa’s Winelands
South Africa’s Winelands are a must-visit destination for luxury travellers. Centred around Stellenbosch, Franschhoek, and Paarl, this region is a magnet for wine lovers. You’ll also find an excellent variety of hotels to choose from. What’s more, you can enjoy high-end luxury for less in the Winelands. As all the wines are South African and the food is locally sourced, you can dine on the finest vintages paired with oysters for outrageously competitive rates.
Read
A Perfect Gay Wedding In South Africa
You’re planning a wedding and honeymoon, and you want somewhere that can actually carry both. South Africa is unusually good at that. You can get married overlooking the Atlantic in Cape Town, among the vineyards of Franschhoek, or at a safari lodge with the bush stretching out behind you. Then the honeymoon can begin without changing countries.
Read
Stellenbosch vs. Franschhoek: Which is Better?
When visiting South Africa’s Winelands, choosing between Stellenbosch and Franschhoek can be a challenge. Both destinations are celebrated for their world-class wines, stunning scenery, and luxurious hotels. Yet, each destination offers a distinctly unique experience. Whether you’re drawn to Stellenbosch’s historic charms or Franschhoek’s European style, your journey to the Winelands will be unforgettable.
Read
Why Rovos Rail Is One of the World’s Greatest Train Journeys
There are luxury train journeys, and then there is Rovos Rail. Often described as the most luxurious train in the world, Rovos Rail offers a style of travel that feels increasingly rare in the modern age. While most journeys today are focused on getting from one destination to another as quickly as possible, Rovos Rail celebrates the romance of slow travel.
Read
Best Gay-Friendly Safari Lodges in Africa
Africa is home to the world's most spectacular safari experiences, where you can pursue the Big 5 through the bush. Picking the right lodge is key to making your safari a success, and if you’re LGBTQ+, the process is more nuanced. Clearly, Africa is not as gay-friendly as Europe, especially outside of South Africa, the de facto gay capital of Africa.
Read
Tours through Winelands
South Africa Food & Wine Tour in the Winelands
Tailor-made HolidayFrom 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.
12 days tailor-made from £9,195 per person View trip
The Best Luxury Hotels in South Africa’s Winelands
Tailor-made HolidaySouth Africa’s Winelands are not only a playground for wine lovers but also home to some of the most luxurious accommodations in the world. Surrounded by rolling vineyards, and mountain ranges, these hotels combine world-class service with South Africa’s finest wines. You can enjoy special perks, such as wine-themed spa treatments, as well as gourmet dining. Wine tourism in South Africa goes beyond tastings.
7 days tailor-made from £3,000 per person View trip
Ultimate Luxury in South Africa: Safari, Winelands & Cape Town
Tailor-made HolidayThis itinerary offers the pinnacle of luxury when it comes to visiting the sparkling jewels of South Africa. With time in both the country's most exciting cities and sprawling natural landscapes, experiencing the country's best hotels and most exclusive experiences, you'll be able to appreciate South Africa's unique cultural and natural wonders without ever compromising on a truly exceptional sense of luxury.
8 days tailor-made from £5,460 per person View tripNo two trips we plan are the same. Yours will be no exception.
Frequently asked questions
Travelling with Out Of Office
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.