A beautiful picture of the Adventurous Cape Peninsula & Overberg Hike tour

Adventurous Cape Peninsula & Overberg Hike

5 Nights

From $1987 USD

for two sharing

Tour Highlights:

breath-taking views from Table Mountain
the splendor of the Kirstenbosch flora
unequalled bird variety at Strandfontein

Adventurous Cape Peninsula & Overberg Hike

Journey Overview

Welcome to your Cape Peninsula adventure travel experience! Your Cape Peninsula hiking journey begins with a private airport transfer from Cape Town International to Parker Cottage, Cape Town. You’ll have time to acclimate to the city and enjoy a comfortable overnight stay in this Victorian mansion. The adventure kicks off on Day 1 and Day 2 with a full-day hike up Table Mountain from the City Bowl, immersing you in the stunning landscapes the Cape Peninsula has to offer.

On Day 3, you'll explore the natural splendor of Kirstenbosch and the wetlands at Strandfontien, making it an ideal day for both birding and walking enthusiasts. You’ll overnight at The Vineyard Hotel in Constantia on this night, as you continue your Cape Peninsula hiking adventure.

Day 4 takes you to the northern part of the Cape Peninsula, where you'll spend a full day hiking through the breathtaking Cape of Good Hope Nature Reserve. Following your adventure, you’ll overnight at The Vineyard Hotel in Constantia once more.

Day 5 of your Cape Peninsula adventure leads you east toward the Overberg coast. Explore the Harold Porter Botanical Gardens and choose between the Kogelberg Biosphere or the Rooisands Nature Reserve for a picturesque walking experience. Afterward, unwind and relax at the Oude Werf Hotel in the heart of historic Stellenbosch, complete with well-deserved rest and massages.

Your Cape Peninsula adventure continues the following morning with a private Winelands tour, including a five-star picnic at Vergelegen. The journey concludes with a transfer to Cape Town International for your flight home.

For those seeking additional days of adventure travel, consider the following options:

Day 6: Venture north from Stellenbosch to the DuToits Kloof Pass for a hike in the area, ending the day at the Montagu Country Hotel, located at the far side of the Cape Winelands in Montagu.

Day 7: Traverse the Sir Lowry’s Pass and arrive at the Wildekrans Country House, nestled within the fruit-growing region of Elgin. Enjoy sections of the Green Mountain Trail and experience the exceptional hospitality provided by Barry and Anne in their enchanting garden.

Embark on this unforgettable adventure travel experience, immersing yourself in the beauty of the Cape Peninsula through various hiking excursions and explorations.

DAYS 1 - 2

Nature's Wonders on Table Mountain

  • Your Accommodation

    Parker Cottage, a historical gem, has been transformed into a grand mansion with 10 exquisite en suite bedrooms, all while preserving the authentic allure of the building. It now offers the modern comforts you'd expect at a four-star establishment. What sets Parker Cottage apart is its commitment to sustainability, as it operates almost entirely off the grid for water, electricity, and heating/cooling. Additionally, it proudly holds Fair Trade Accreditation.

    Your home away from home:

    Parker Cottage
    3 Carstens Street, Tamboerskloof
    Tel +27 21 424 6445

  • Your Travel Time

  • Your Activities

    Your adventure begins with a warm welcome at Cape Town International Airport. Our friendly driver and guide, Chris Hannival, will be there to greet you and start your journey in the beautiful Mother City. As you arrive in town, take a moment to unwind and immerse yourself in the charming neighborhood of Tamboerskloof, where the elegant Parker Cottage is nestled. You might consider a leisurely stroll to Kloof Street, a local hotspot, where you can savor a cup of coffee and explore the quaint bookshops and art galleries.

    On your second day, prepare for an exciting journey to Table Mountain (weather permitting). Dominic Chadbon, your experienced guide from The Fynbos Guy, will select the best route for the day. Most likely, you'll embark on a 6-kilometer hike through the Valley of the Red Gods. The grand finale of this hike is descending via the cable car from the mountain's summit.

    Table Mountain, spanning 57 square kilometers, offers a variety of routes tailored to your fitness level and interests. Our full-day hikes steer clear of the crowded Table Top and cable car area, ensuring a more personal experience. The morning ascent is punctuated with a coffee break featuring fresh chocolate croissants or muffins. You may choose to explore the 12 Apostles side of Table Mountain, with breathtaking views of the Atlantic Ocean and Lion's Head, or opt for a hike from the Constantia area, offering spectacular vistas of False Bay and the entire peninsula. Customization is key, allowing you to select routes with little to no scrambling or more challenging ascents with added scrambling. A delightful picnic lunch and refreshing drinks await you after the hike. As you explore the mountain, you'll uncover hidden forests, pristine white-sand beaches, enchanting waterfalls, and vast stretches of unspoiled fynbos vegetation.

  • Your Food
DAYS 3 - 4

Exploring Nature's Diversity in Cape Peninsula

  • Your Accommodation

    For your overnight stay, we'll take you to The Vineyard Hotel in Newlands (Constantia). This historic hotel, with over 200 years of heritage, sits on six acres of lush landscaped parkland along the Liesbeek River. What makes it unique is its Regency architectural style, a departure from the typical Cape Dutch design of its time. Once the home of Lady Anne Barnard, the hotel underwent extensions designed by renowned architects Jack Barnett and Revel Fox. It's adorned with works by leading South African artists and offers a range of rooms, from singles to family suites, all with either mountain or courtyard views.

    You can also unwind with two swimming pools, one outdoors with comfortable loungers and an indoor heated pool. After a long day, pamper yourself at the world-class on-site spa.

    Your home away from home:

    The Vineyard Hotel
    Colinton Road, Newlands
    Tel +27 (0) 21 657 4500

  • Your Travel Time

  • Your Activities

    On the morning of Day 3, we'll pick you up early from Parker Cottage and head southeast, leaving the heart of Cape Town behind. Our journey will take you to two premier bird-watching destinations that also serve as fantastic introductions to the rich variety of plant life in the area.

    Our day begins with a visit to Strandfontein Water Treatment Works, an exceptional birding spot teeming with life. Here, you'll encounter hundreds, if not thousands, of flamingos alongside pelicans, waders, wildfowl, sea birds, and various raptors such as fish-eagles, harriers, and kites. This site also provides a glimpse of what the Cape Flats once looked like, with lush vegetation and extensive wetlands. Following this birding adventure, we'll enjoy a picnic lunch.

    Next, we'll make our way to Kirstenbosch Botanical Gardens, a place where coastal and wetland experiences from Strandfontein are balanced with magnificent examples of fynbos and natural forest. This is a paradise for botanists, but it's also a haven for bird enthusiasts. You'll have the opportunity to spot mountain, thicket, and forest bird species in the beautiful garden surroundings. The tame nature of the birds in the gardens makes it an excellent spot for photography. Look out for all three local Sunbirds, Cape Sugarbirds, and Eagle-Owls.

    Day 4 begins with an early pick-up to ensure you arrive at Boulders Beach penguin colony as the gates open, providing a magical experience with more bird sightings than later in the day. A short walk will lead you to a sheltered beach, a well-kept secret, where you can enjoy a picnic breakfast with penguins often wandering past you. After breakfast, we'll make our way to the Cape of Good Hope Reserve.

    Our itinerary here depends on the tides and the time of year. You might start by exploring the teeming tidal pools of Black Rocks on the Indian Ocean coast or opt for a hike along the rugged Atlantic beaches, complete with shipwrecks and the eerie remnants of bleached whale bones. The reserve is a wildlife haven, with opportunities to spot various antelope, ostriches, baboons, tortoises, and an array of bird species. A picnic lunch will be served at the seldom-visited yet excellent information center, equipped with bathrooms.

    As the day unfolds, we'll head to Cape Point for stunning views in the late afternoon. To cap off your day, we'll treat you to a scenic drive back to Cape Town via Chapman's Peak Drive and the breathtaking 12 Apostles. This will be a day filled with remarkable wildlife encounters and unforgettable natural beauty.

  • Your Food

    The hotel boasts two exceptional restaurants: "The Square" for breakfast, dinner, and a popular sushi bar, and Myoga Restaurant, known for its modern fusion cuisine, open for lunch and dinner.


Coastal Marvels, Penguins, and Botanical Wonders

  • Your Accommodation

    For your evening stay, we have a special treat in store for you at the Oude Werf. It's not just the oldest continuously operating hotel in South Africa, with a history spanning over three centuries; it's also a prime example of a place where tradition meets modernity. The hotel proudly holds the coveted Fair Trade Accreditation, reflecting its commitment to ethical and sustainable business practices while providing an exceptional guest experience.

    At the Oude Werf, you can indulge in in-room massages to relax after all your hiking adventures, savor great coffee at the lounge, enjoy room service, and relish the superb food and wine. Locals frequent this establishment, a testament to its excellence. Surprisingly, the building that houses the hotel has faced destruction by fire three times in its history. Originally constructed in 1686 as a church, the modern building dates back to 1880 and underwent a complete transformation into a hotel in 1973. To this day, it remains a family-owned and operated gem, overseen by the Pistorius family, who are present on-site most days.

    Your home away from home:

    30 Church street, Stellenbosch
    Tel . +27 21 887 4608

  • Your Travel Time

  • Your Activities

    Today, we bid farewell to the Cape Peninsula and embark on a day filled with awe-inspiring coastal scenery. As we venture out of Cape Town, we'll travel along the eastern edge of False Bay, treating you to more breathtaking vistas. If you're visiting in spring, keep an eye out for the majestic southern right whales that grace these waters.

    Our first destination is the Stony Point penguin colony in Betty's Bay. It's a true haven for nature enthusiasts, where thousands of African penguins share the landscape with cormorants, gulls, and dassies (hyraxes). This site is also an ideal place to explore the marine ecology of the Cape, with seashells, seaweeds, and, if the tide is low, fascinating rock pools to discover.

    A short drive will take us to the picturesque Harold Porter Botanical Gardens, a hidden gem similar to Kirstenbosch but without the crowds. Here, you can immerse yourself in the world of Cape's fynbos. We'll enjoy a delightful picnic lunch under the shade of a tree and take a stroll to the back of the gardens, where wild forests and stunning fynbos landscapes await. The gardens also provide excellent bird-watching opportunities.

    Our journey will then lead us into the heart of the fynbos, the Kogelberg Biosphere. Here, you'll be surrounded by incredible fynbos vegetation, and the moment we deviate from the road, you'll have a chance to spot rare mountain birds.

    As an alternative, we might visit the Rooisands Nature Reserve in Kleinmond, renowned for its water birds and the occasional sighting of wild horses.

  • Your Food

Stellenbosch Serenity and Picnic Farewell

  • Your Accommodation

    On your final day, we recommend spending your time leisurely exploring the charming streets of Stellenbosch. These avenues are adorned with enchanting jacaranda trees and majestic oaks, and every corner reveals a rich tapestry of history and old-world architecture.

    In the late morning, you'll be picked up by Chris Hannival, but before concluding your memorable journey, we have a delightful stop planned for you at Vergelegen. This exceptional wine estate, located near the town of Somerset West, offers a picnic experience like no other. You'll be seated in a serene wooded glade on comfortable chairs, complete with a table. To add to the magic, a dedicated waiter will bring you a picnic basket filled with culinary delights. It's the epitome of leisure and indulgence.

    After savoring your picnic, Chris will accompany you to Cape Town International Airport, concluding your adventure with a convenient and comfortable drop-off.

    We hope you've enjoyed this tour of Cape Town and its surrounding gems. It's been a pleasure sharing these remarkable experiences with you, and we look forward to welcoming you back to this beautiful region in the future. Safe travels!

    Your home away from home:

  • Your Travel Time

  • Your Activities
  • Your Food

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Contact Us

Exceed House
Springfield Office Park
Belleville, Cape Town

Cell / WhatsApp +27 72 136 9096

WhatsApp +27 72 136 9096

Email: travel@whereitallbegan.co.za

Contact Us


We’re an ethical private travel planning company focused on Southern Africa.

We offer ready-made and also customised holidays and journeys across this unique region of the world.

When our clients travel with us, they are assured that their travel spend is directly supporting local African companies that offer sustainable products and services, both in terms of people and planet.


Our logo is an image of a skull found in the Rising Star Cave System in Gauteng, South Africa in 2013. It was named ‘homo naledi’, meaning ‘human of the stars’.

The cave system has so far given rise to the remains of over 15 individuals, making it the largest hominid fossil remains site ever discovered.

Travelling to Southern Africa is truly a return to the source of humankind, to Where It All Began.

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