Tailor-made Vacation · South Africa
Cape Town & Franschhoek: Wine Region Tour
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 carefully crafted itinerary offers a truly exclusive and boutique experience of South Africa, allowing you to immerse yourself in the country's finest boutique hotels.
Your adventure begins with five days in a beautiful boutique hotel, nestled on the slopes of the iconic Table Mountain. Here, you'll enjoy the perfect blend of luxury and intimacy, with the added convenience of having your own rental car at your disposal. This means you can explore the captivating city of Cape Town at your own pace, taking in the breathtaking sights such as the majestic Table Mountain and the historic Robben Island.
Read more
With Kensington Place as your base, you'll have the opportunity to delve into the rich cultural tapestry of Cape Town while indulging in the comfort and personalized service of a boutique hotel.
After your stay in Cape Town, the journey continues to the wine regions of South Africa. You'll stay in beautiful Franschhoek, renowned as the country's gourmet capital. Here, you'll experience the epitome of culinary excellence and vineyard splendor. The idyllic charm of Franschhoek, with its lush vineyards and quaint streets, will captivate your senses.
As you savor the world-class wines and cuisine that Franschhoek has to offer, you'll find yourself immersed in the cultural and gastronomic tapestry of the region. The contrast between the bustling city of Cape Town and the tranquil beauty of Franschhoek will make this journey a well-rounded exploration of South Africa's diverse landscapes and experiences. To stay for longer, consider adding on a few nights at one of our handpicked safari lodges in the region.
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 5: Cape Town
Upon arrival, you’ll be able to pick your hire car and head to Kensington Place.
This contemporary boutique hotel combines cutting-edge design with a tranquil but prime location on the slopes of Table Mountain. And as it has just eight bespoke guest rooms and a team of friendly staffers who are almost telepathic it’s not such a stretch to feel you’re staying in a private home.
Yet this is a private home styled by someone with immaculate taste, the finest linens used on the beds, the thickest towels used in the bathrooms and flat-screen TVs, iPod docking stations and personal laptops with Wi-fi just a few of the modern accessories. There’s even a plunge pool to cool you down.
Day 5 to 8: Wine Region
Staying at The Last Word Franschhoek, you’ll find 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 recognized 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.
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
Similar trips
Gay Group Trip: Cape Town to Botswana Safari
Group TripExperience the headline-act version of Southern Africa on this tailor-made nine-day LGBTQ+ safari itinerary, moving from Cape Town through Victoria Falls into Botswana's Chobe National Park and the Okavango Delta. Three countries, four distinctly different stops and a hotel collection that anchors the trip at the right level for a couple ready to spend on the right places.
9 days group departure from $9,900 per person View trip
Discover KwaZulu-Natal: Bush, Beach & Culture
Tailor-made VacationWelcome to South Africa’s KwaZulu-Natal - a region where golden beaches, wildlife-filled wetlands, and mountain kingdoms come together in one remarkable province. This curated 11-day itinerary invites you to slow down, reconnect, and experience the rich natural and cultural heritage that makes this part of the world truly unforgettable.
11 days tailor-made from $10,480 per person View trip
Exclusive South Africa Safari: Kruger Big Five & Tswalu Kalahari Adventure
Tailor-made VacationDiscover two of South Africa’s most extraordinary gay-friendly safari destinations on this highly exclusive journey, combining the legendary wildlife of Greater Kruger with the raw, untamed beauty of the Kalahari. Your curated 10-day adventure begins in Timbavati Private Nature Reserve. Here, the Big Five roam free and intimate lodges bring the bush to your doorstep.
10 days tailor-made from $25,190 per person View tripSee the whole trip, priced in full, before anything is confirmed.
Frequently asked questions
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specializing in tailor-made vacations and extraordinary journeys around the world. We create bespoke luxury vacations, 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 personalized 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 traveling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveler, 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, personalized service and discretion.
Do you create tailor-made LGBTQ+ vacations?
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 personalized 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+ travelers 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 traveling 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 inquiry to homecoming. No call center, and nothing is charged until you decide to book.