We live in boutique apartments instead of hotels or hostels to have that homely feel abroad. Our apartments are hand-picked to have comfort and privacy.
We’ll pick you up from the airport and organize transportation to our events outside Cape Town. You can expect a warm welcome from Victor.
Our team will be curating all the local experiences and you can rely on them to help personalize your time in Cape Town
Trip to Cape Point and the Penguins
BoKaap Food Crawl
Sharan has lived in Cape Town for a year, and he’ll be curating the experience with all our local partners – expect lots of sunsets, coffee, and wine. You can rely on him for logistics before and during the trip.
A Cape Town resident, Victor manages transportation and is the first person you’ll see in Cape Town. He loves getting to know the group and talk about life in and out of South Africa.
We team up with amazing locals who become our experience designers and friends in each city. You can rely on them to provide recommendations on what to do, where to eat, and anything else.
Up to 15 other inspiring creatives, designers, founders, marketers, and other professionals. Check out our Community page to learn more about the type of people you can expect in South Africa.
Unlike tour companies, we don’t just use a cookie-cutter itinerary for every trip. Each trip is unique and incorporates local events like summer festivals, markets, and the weather. We provide our curated schedules to the group a week before the trip, but here’s how we plan to journey through Cape Town!
A big reason for hosting this trip from November – March is the start of the summer concerts in the Kirstenbosch Botanical Gardens. Imagine an outdoor live music event with local artists, and a gorgeous mountain as the backdrop. Add in picnic blankets, wine, and your fellow travelers for an evening of music and great weather.
Both Lion’s Head and Table Mountain are iconic landmarks in Cape Town, and we’d recommend hiking both if you’re up to it.
The sunset hike to Lion’s Head is catered to all skill levels. We’ll start early to grab our sunset spot at the top and enjoy the beautiful views of the city and Table Mountain behind it. The hike can be steep, but don’t worry, we’ll do it together.
The sunrise hike to Table Mountain is geared to the more adventurous hikers. If hiking for five hours isn’t your thing, you can take the cable car up and enjoy the same views without a sweat!
Instead of eating at the touristy restaurants in the city, we’ll be having dinner in Langa, to spend an evening with the community and mingle with our local friends. Most tourists diminish their experience by just doing “township tours,” but that’s not our style. We’ll spend the evening with our family hosts, eat home-cooked South African food, and indulge in some meaningful conversations.
Stellenbosch, Franschhoek, and Constantia have world-class wineries, producing some of the best Chenins and Pinotage. We’ll dress up for a bougie evening of local wine and cheese and explore three different vineyards in Stellenbosch and Franschhoek. Bring your favorite summer dresses and linen shirts – there are going to be plenty of pictures and a beautiful sunset to end the evening.
The Cape Malay quarters is one of the most diverse and historic parts of town. It’s where the paths between South Africa and the Malaysian and Eastern settlers, originally brought in as slaves by the Dutch, collided. Over time, these neighborhoods became a melting pot for cultures, religions, and of course food. We’ll walk around the Cape Malay quarters, learning about its history, and indulging in all the delicious food.
We can’t come to South Africa and not say hello to the Penguins. We’ll start this full-day experience with a breakfast at the Rhodes Memorial and make our way to the old lighthouse at the Cape of Good Hope, the southern tip of the Cape Peninsula. Roll up your windows, for you may encounter random baboons stealing your evening snack! After a little hike to Diaz Beach, we’ll make our way to meet the waddling Penguins on Boulders Beach and wrap up with a relaxing sunset on Chapman’s Peak.
We’ll be staying in a trendy neighborhood in the center of town, close to all of our favorite coffee shops and restaurants. Each apartment has private rooms and bathrooms for all our members — we don’t do shared hotels or hostels. Here are some photos of places we usually stay at:
Continue the adventure for 4 extra days to experience the wildlife of South Africa
Wildlife safaris in Kruger are one of the most exhilarating experiences. Get close to its spectacular animals in their natural habitat and explore its vast landscapes. Multiple safaris at different times of day ensure optimal game viewing and the best chance to see the Big 5. Another highlight of this extended trip is the scenic Panorama Route that takes in impressive views of the Blyde river canyon and much more.
Add On Cost: $975
The OOO Club gave me the experience of a lifetime. Every day was a new adventure. Whether it was singing at an open-air concert, climbing to the tops of mountains, swimming between oceans, or dancing under the moonlight. This trip lit my soul in a way that had been dormant for far too long.
OOO hit it out of the park. The week was curated so thoughtfully with each day better than the last. I felt like I was adventuring with someone who knew all the secrets of the land. Epic is an understatement! Thanks, OOO, for an experience I’ll never forget.
The OOO Club has thought of all the key ingredients for making a trip special: creating a community of like-minded wanderlusters, creating experiences that are better enjoyed with a group, adding special details and moments, including a local specialist that makes the trip less touristy. Overall, the club, for me, is the perfect way to travel.