Cape Town & Culture of the Western Cape

All Images & Video Shot On Location
by Gene Taylor

Cape Town

The Western Cape & Cape Peninsula



Culture of the Western Cape

from $698 a person

Main Event


Cape Town Marathon

Table Mountain Trek

from $1998 a person


3 - Night Safari

from $2398 a person

6-Night Safari

$3898 a person

Registration Forms

Register for the

adventure of a lifetime. 

Come Walk, Run, Hike, Trek,

Trail Run and Peace Walk With Us!

​This is an amazing 60 hours in Cape Town & The Peninsula!

Begin your journey by expecting the unexpected. A walk with the penguins!

"I have traveled and led adventures throughout 10 countries in Africa and over the years I’ve visited many cities and cultural centers. We have loaded the two days of this trip with as much local flavor and fun, along with a more serious experience of learning about South Africa's recent history and the cultural transformation that is nothing short of miraculous. Our goal is provide access to the people who live here so they can share their journey so you can understand firsthand about what is life like here."                ~Gene Taylor, Co-Founder~

We'll depart Cape Town after breakfast and head toward Chapman’s Peak Drive. It winds it way through the mountains and along the coast to the south-western tip of South Africa and its iconic Cape Of Good Hope! This is one of the most spectacular marine drives anywhere in the world. Choose from a challenging hike up to the Cape Lighthouse, or a relaxing ride on the funicular. From here we'll take a slow walk downhill to the iconic Cape Point Sign for a team photo. Cape Point is a spectacular sight and home to breathtaking bays, beaches and rolling green hills and valleys, just 60km outside of Cape Town. There's more. The Boulders are home to the famous colony of Jackass Penguins, so called for their hilarious braying call. Weather permitting, you have the opportunity to walk among the boulders and local wildlife. There is more to explore in Cape Town than you can imagine. From e-bikes along the coast to shopping at the V&A, from  swimming with seals to visiting one of the world's most beautiful botanical gardens, Come Explore The Cape With Us! 

Register by Dec. 31st
& Receive $200 - $400 discount on Our 3x & 6x COMBO Bundles (Pre, Main & Safari)!
Click to Learn More
& Register.

Think Adventure Suits YOU?

Here's What You Can Do In 10-Days In South Africa With Your Teammates & iConquer!

Visit the Cape of Good Hope! Then, cage dive with sharks, go wine tasting, walk with penguins, run a marathon, tour Cape Town, Summit Table Mountain, party with friends, see a rhinoceros, giraffe, lion, cheetah, gazelle, baboons and wildebeest all in one day, dine in a "boma," hear lions roar in the distance as you sleep, see curious monkeys sway the treetops, take a picture of elephants, gazelle, impala and zebra with just one shot, sleep in a permanent tented camp, sip a beverage as the sun sets over the Indian Ocean, dine while nearby hippos tussle and snort at each other, and perhaps the biggest thrill of all, see the circle of life unfold between predator and prey. Lion, wild dogs, leopard, cheetah, hyena, crocodile -- impala, buffalo, zebra and gazelle. Ground scavengers and birds finish whatever is left. More things: Go to a rooftop party, walk the Indian Ocean coastline, dine al fresco in a South African vineyard, imagine you're in a movie with Meryl Streep or Robert Redford, visit Robben Island and walk in the footsteps of Nelson Mandela. And that is only following the outlined activities! There is also plenty of free time for you to explore on your own.

2020 DATES

Trek & Marathon
October 15 - 19

Pre-Cape Peninsula - Oct. 13 - 14
Post-Wildlife Safari - Oct. 19 - 22
Extended Safari - Oct. 19 - 25


from $698
per person, dbl. occ.


2 - Night Cape Point

4 - Night - Trek & Run
3 - Night Wildlife Safari/

6 - Night wildlife Safari 


Easy to Moderate

click HERE for more info 

about Activity Levels


Small Private Group



iConquer Adventures

Walking Connection

Expect The Unexpected...

Patrick and I were just reminiscing about where we were a year ago, and the adventure that we shared with you in Africa!
It was really the highlight for 2017! The people, the land, the animals, the quiet, the dear fellow travelers, the ease at which we traveled through our safari - all the very best!

Thank you for creating such a memorable moment in time!

CARLA, Tanzania, '17

Your Cape Town 

Pre-Adventure Includes:

  • Walking Connection Guest Services throughout. We do the details!

  • We'll meet and greet you at the Cape Town Airport.

  • 3-Day/2-Night Cape Town Cultural Adventure.

  • 2-Nights Accommodations chosen for their excellent location, service and comfort. (See the Main Event for details).

  • Full Day of Guided Walking Tours including: Cape Lighthouse, Boulder Beach & Cape Point/funicular, transport and lunch.
  • Hosted and/or guided sightseeing along the stunning Chapman's Peak.

  • Experienced interpretive and naturalist guide(s) on walks and drives.

  • Small private group.

  • All park fees, sanctuary fees, conservation fees, site entries, government taxes and statutory charges as listed on the itinerary *(See Price Variation Below).

  • Planning Assistance. We'll help you plan your adventure!

  • Detailed Know Before You Go information including packing list, weather forecast, recommended reading lists, websites and more!


*PRICE VARIATION – Prices are based upon the current government fees for park, camping, concession fees and sanctuary entry and all taxes at the time of publication of this web page. Should the government impose any new taxes, raise the current tax or increase the entry cost to any park or sanctuary, the price increase will be passed along and charged to you. You will be notified of this increase at the time we are notified. All payments received by us are subject to the cancellation policy already published and in effect.


Your Cape Town Cultural Adventure Itinerary

*Itinerary: Please note that the details of this itinerary are subject to change. Many of the planned activities are organized according to availability, events or seasonal dates, appropriate weather conditions or the discretion of our guides. We make every effort to provide the experience described in the itinerary with the understanding that some things may change.


Day 1 – Oct. 13 - Cape Town

Arrival Cape Town 

Plan for a late evening arrival in Cape Town. You'll be a bit weary from your long flight and we want you to feel welcome, so we'll meet and greet you at the airport and assist you with getting to the hotel. 

The Radisson Red Hotel will be our home and host property during our stay in Cape Town. We selected this property for its proximity to the Sanlam Events, the Adventure Trek and Victoria & Alfred Waterfront, the starting point for all activities. It's in the center of everything and has a cool rooftop pool!

Accommodation: Radisson Red - Night 1 of 2


Day 2 - Oct. 14 - Cape Peninsula

Cape Point, Boulders Walking Tours!

After breakfast meet our local resident interpretive walking guide for a full day adventure.

Chapman’s Peak Drive winds it way between Hout Bay and Noordhoek. Situated on the Atlantic Coast, at the south-western tip of