map of south africa

Cape Town

A coming together of cultures, landscapes, and cuisines. The Mother City is a melting pot of people, squashed between the ocean on one side and mountains on the other.

  • 7 Days Cape Town

    7 Days Cape Town

  • +4 Days Safari

    +4 Days Safari

Cape Town


Extend your trip by 4 days to experience wildlife safaris in Kruger National Park

Cape Town

CURATED LOCAL EXPERIENCES IN CAPE TOWN

  • Welcome social at an outdoor terrace

    Welcome social at an outdoor terrace

  • Sunset hike to Lion’s Head

    Sunset hike to Lion’s Head

  • Wine tasting in Stellenbosch

    Wine tasting in Stellenbosch

  • Sunrise hike to Table Mountain

    Sunrise hike to Table Mountain

  • Dinner at a family’s home in a township

    Dinner at a family’s home in a township

  • Picnic at the Kirstenbosch Summer concert

    Picnic at the Kirstenbosch Summer concert

  • BoKaap food crawl

    BoKaap food crawl

  • Cape Point experience and meet the Penguins

    Cape Point experience and meet the Penguins

2022 DATES

Feb 12 - 19, 2022
Apr 2 - Apr 9, 2022

Private Rooms

$1,890

Get your own bedroom and bathroom with 1-2 other apartment-mates

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Shared Rooms

$1,590

For the couples or friend duos who can share the fun

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WHAT’S INCLUDED

Private rooms in boutique apartments

Private rooms in boutique apartments

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.

Curated experiences led by us

Curated experiences led by us

  • Welcome social
  • Sunset hike to Lion’s Head
  • Wine tasting in Stellenbosch
  • Sunrise hike to Table Mountain
  • Dinner with a family in a township
  • Picnic at the Kirstenbosch concert
Driver Cape Town Men

Local transportation

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 kick-ass OOO team on the ground

Our kick-ass OOO team on the ground

Our team will be curating all the local experiences and you can rely on them to help personalize your time in Cape Town

What’s optional

What’s optional

Trip to Cape Point and the Penguins

BoKaap Food Crawl

WHO’S GOING

Sharan

Sharan Community Lead

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.

Victor

Victor Transport Lead

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.

Local Partners

Local Partners

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.

OOO Community

OOO Community

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.

Exploring Cape Town

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!

Kirstenbosch Summer Concert

Kirstenbosch Summer Concert

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.

A Tale of Two Peaks – Hiking Lion’s Head and Table Mountain

A Tale of Two Peaks – Hiking Lion’s Head and Table Mountain

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!

Dinner in Langa Township

Dinner in Langa Township

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.

Wine tasting in Stellenbosch and Franschhoek

Wine tasting in Stellenbosch and Franschhoek

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.

BoKaap Food Crawl

BoKaap Food Crawl

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.

The Penguins and Cape Point (add-on)

The Penguins and Cape Point (add-on)

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.

WHERE WE LIVE

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:

Kruger National Park

Kruger National Park

Extend your trip to Kruger National Park

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

This Extended Trip to Kruger includes:

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    Flight to Kruger Mpumalanga International Airport
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    Private transfer to the lodge from the airport
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    Three nights in a boutique lodge close to Kruger National Park
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    Daily breakfast
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    Late afternoon open 4x4 wildlife safari
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    Full-day open 4x4 wildlife safari
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    Morning walk safari
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    Panorama Route day trip
Extend your trip to Kruger National Park

Testimonials

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.

SumerToronto

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.

KamalpreetSacramento

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.

BeckySan Francisco

PAST EXPERIENCES

Watch one of our past experiences

Cape Town Aftermovie

Croatia Aftermovie