The Chile Experience

Johannesburg + Luxury Safari Trip + Cape Town

There aren’t very many places in the world where you can shake your mane with a lion, shop from a grip of Black-owned stores, and eat a delectable meal prepared with ingredients you personally foraged.
Join us on our 11-day luxury adventure in South Africa and experience the country’s culture on a deeper level than the limited Apartheid narrative you’ve been told. You can’t call yourself woke until you have experienced our ancestral home for yourself.

Do you hear that? That’s the sound of your tastebuds singing after you savor the local culinary magic at Neighbourgoods Day Party & Market, sip sommelier-selected wines in the winelands, and swoon over the traditional fare and captivating storytelling at the Yeoville Supper Club.  

And you didn’t come snatched for nothin’! The pics you will snap of your melanin poppin’ in front of the brightly colored homes of Bo-Kaap will be enough to shut down the gram, no cap.  

Whether you are soaking it in on a cruise, in a helicopter, or from the top of Table Mountain, the breathtaking scenery will make you feel blessed to experience the beauty of the Motherland. 

Priceless moments with new friends, historical exploration, and pampered relaxation await you on your Up in the Air Life journey through South Africa.

Love the trip but not the dates?



Here's your trip at a glance.


From exploring the concrete jungle to embarking on safari, this trip offers a wide variety of scenery (and selfie) options. You will be able to check must-see sites like Nelson Mandela’s House, Shambala Private Game Reserve, and Robben Island off your bucket list.


This trip is your chance to be classy, bougie, and a little ratchet. From dining on food created by the finest chefs and learning about the unexpected nuances of Nelson Mandela's story to Kiking at the most lit parties, you will experience the spectrum of South Africa's multifaceted culture.


Our accommodations are so extra. After a long day admiring the majesty of elephants, finding the best deals in the market, or soaking in the sites, you will relax in a sumptuous private villa, garden lodge, or freestanding suite. Only the best for Lifers!

Explore the day-by-day itinerary.



Day 1

Welcome to Johannesburg, South Africa!
After you’ve checked into your luxurious accommodations and had a chance to rest up, we will toast it up at Sanza’s, Yeoville’s now-famous South African denizen. He offers a culinary family-style dinner journey fusing vegan vibes, cocktails, wine & storytelling with traditional food from every corner of the continent.

Day 2

Today, we’ll learn the history of Apartheid by visiting the renowned Apartheid Museum, Nelson Mandela’s House, and other historic sites. Then, we’ll learn famous dance routines from surviving Pantsula dance crews.
After we’ve worked up an appetite, we’ll head over to enjoy an amazing Soweto Braai lunch and see Soweto beyond boisterous Vilikazi Street. Tonight, you’ll enjoy a free evening out on the town with our recommendations.

Day 3

Today, we take the global phenomenon of a ‘Day Party’ to the motherland, South-African style. We’ll head to Neighbourgoods Day Party & Market which offers a vibrant blend of delicious food, mouth-watering drinks and exceptional music and dancing!
After enjoying the sights and sounds, we’ll experience some of Joburg’s most famous drinking spots – from trendy rooftop bars to underground pubs and historic watering holes — so you can let your hair down and discover a city undergoing a remarkable rebirth.

Day 4

Take some time for you; relax and enjoy Jozi with our tour leaders eager to provide assistance & experiences on demand for anything you’d love to see and do in the city.
Prior to your trip, we provide a list of optional tours you may purchase, or feel free to simply “play it by ear.”

Day 5

Today, we’ll venture out to the neighboring province of Limpopo for an unparalleled luxury safari where you’ll see “The Big 5” up close and personal.
By nightfall, you’ll return to your lavish lodge for relaxation & reflection.

Day 6

There is nothing quite like a leisurely sundowner cruise on the 30 hectare Douw Steyn Dam, the largest man-made dam in southern Africa. Today, we’ll visit the dam and scout for herds of hippos, crocodiles, and a large and a large, varied indigenous fish population.
In the evening, we’ll gaze up at the Milky Way as it stretches out across the sky, bringing a renewed sense of peace and adventure.

Day 7

Awaken to a glorious African sunrise and delectable breakfast before we head out on our final African Safari game drive prior to journeying back to Jozi to fly to Cape Town.
Tonight, you’ll have free time to wind down from our journey and enjoy dinner on your own or with your new-found friends. Don’t worry, we’ll have some dope recommendations!

Day 8

Today, we’ll explore Bo-Kaap, the Cape Malay neighborhood in Cape Town known for its colorful homes, a favorite spot for any Instagrammer. We’ll take a photo tour that misses nothing.
In the evening, we’ll trade the crowded ferry and long lines for a private chopper and explore Robben Island, the notorious prison that once held Nelson Mandela.

Day 9

Enjoy a scenic ride up to the famous Table Mountain, a flat-topped mountain with uniquely rich vegetation that forms a prominent landmark overlooking the city of Cape Town.
We’ll indulge in a delectable wine tasting paired with South African traditional snacks. Then, we’ll wind down the evening at the hotel spa or enjoying a night on the town.

Day 10

Today, we’ll join our chef and expert sommelier on a culinary journey in the winelands as we forage for ingredients, experience a guided cellar tour, and enjoy an out-of-this-world lunch with expertly matched wine pairings.

Day 11

Rise and shine for an optional self-guided tour or shop your last hours away.
When it’s time, our private drivers will whisk you away to the airport, where you can start planning your next adventure with new friends.

No matter where you travel, our standards are the same.


Connect with amazing people.

We provide the opportunity to make friendships with people who share your worldview and won't ask why you wear a bonnet to sleep.

Experience attentive
and authentic hospitality.

Not only is the staff of Up in the Air Life dedicated to making sure your trip is flawlessly executed, but we are also intentional about choosing locales and vendors who celebrate Black travelers

Be pampered with only the best.

There is no need to take a break from your baller lifestyle when you travel with us. Our lodging, excursions, and dining are pure luxury.

Feel safe and secure.

Our experienced American guides and well-maintained local relationships mean that you will have peace of mind when you travel with us.

Say "goodbye" to FOMO.

Our trips are anything but basic. While we make sure you see well-known main attractions, we also develop itineraries that will give you unique stories to share with your friends back home.

Can you envision yourself on this trip?

Download "The South Africa Experience" trip brochure and keep it handy as you continue to explore, or take the plunge and book now.