Best of the Cape Peninsula Tour


[Full Day Private Tour] Embark on an incredible journey around the Cape Peninsula with your professional and experienced guide and host for the day, match made to your profile for the very best experience possible. You’ll observe the famous and comical African penguins in their natural habitat at the exquisitely beautiful Boulders Beach. Explore the southern most tip of the Cape Peninsula with its breathaking views, dramatic cliffsides and turbulent waters. Visit the quaint seaside villages of Simon’s Town and Kalk Bay. Taste wine in the historic Constantia Valley. All in a day and completely flexible to suit your rhythm and preferences. Your experienced guide will also be able to adapt your itinerary to suit your rhythm and preferences on the day.

Pickup 8 am ~ 5pm drop-off.

  • Discover the breathtakingly beautiful Cape Peninsula with great spots to take photos
  • Enjoy a scenic drive along the famous Chapman’s Peak Drive, an engineering marvel
  • Visit the Cape of Good Hope Nature Reserve & Cape Point
  • Visit the southern most tip of the Cape Peninsula where the Indian and Atlantic Ocean meet
  • Stroll through the beautiful Boulders Beach, home to the delightfully comical African penguin
  • Visit the quaint seaside towns of Simons Town and Kalk Bay
  • Taste award winning wine at the highest tasting room in the world renowned Constantia valley

Tour Itinerary

  • Pickup

    Your professional and experienced guide will collect you at your hotel or accommodation

  • Cape Point

    Explore the breathtakingly beautiful Cape Point reserve and take the Flying Dutchman Funicular to the top to see the lighthouse

  • Boulders Beach

    Stroll through the beautiful Boulders Beach and see the delightfully comical African Penguin

  • Lunch

    Enjoy lunch with a spectacular view overlooking the ocean or at one of the many fantastic local restaurants (lunch for own account although we'll make all reservations for you)

  • Kalk Bay

    Visit the quaint seaside towns of Simon's Town and Kalk Bay

  • Chapman's Peak Drive

    Enjoy a scenic drive along the famous Chapman’s Peak Drive

  • Go As You Please

    Choose from multiple curated Peninsula experiences with your guide

  • Drop-Off

    Your guide will drop you off at your accommodation (or a predetermined destination should you require)

Tour Highlights

Breathtaking Views
Outdoor Activities
Wine Tastings
Private Tour Guide

Full Details

This fantastic day tour from Cape Town to the Peninsula is designed to expose you to the sheer, breathtaking natural beauty of South Africa. You’ll feel like you’re in a James Bond movie when you cruise over Chapman’s Peak Drive and towards the ocean. The steep cliffs and panoramic views mean that every curve of the road is a great photo opportunity. Your guide will find the best spots to stop along the way to take in the magnificence of your surroundings.

Next, make your way down the Peninsula to the most south-western tip of Africa in the Cape Point National Park. Capture an iconic photo at what seems like the edge of the world. You can choose to walk up the steep path to the iconic lighthouse or take the Flying Dutchman funicular (optional). You’ll experience a 360-degree panorama of the ocean, both peninsula coastlines, dramatic cliffs and the clean white sweep of Dias Beach far below. Mark that off your Cape Town bucket list.

Now you’ll make your way to the famous penguin colony on Boulders Beach to watch the the comical African penguins as they waddle along the beach and frolic in the waves. Take a walk along the wooden walkway over the pristine beach as you get up close and personal with these special creatures. This is the perfect time to get that classic ‘up-close-and-personal’ picture with these feathered fellows.

After making some new tuxedoed friends (the penguins), take a stroll through a nearby naval base called Simon’s Town, the official home of the South African Navy. Discover the rich history of this seaside village and its maritime strategy that played an inseparable role in the history of the Cape of Good Hope and South Africa as a whole.

Next, enjoy a casual lunch in the quaint seaside fishing village, Kalk Bay (or get in touch directly and we can arrange something special for you or book a restuarant for you based on your preferences).

By now you’ll be ready for some wine tasting! Make your way to the historic Constantia wine valley where you will head up the mountainside to enjoy wines from the highest tasting room in the Valley. Enjoy epic views as you drink  award winning wines (this can also be subsistuted for a visit the the fantastic Kirstenbosch National Botanical Gardens or something of your preference…just let us know and we’ll build it into your itinerary!).

Rate includes: Pickup and drop-off from your accommodation in and around Cape Town, private and professional, experienced guide (who is also your driver depending on the size of the group), toll for Chapman’s Peak Drive, entrance fee to Boulders Beach, entrance fee to Cape of Good Hope Nature Reserve, 1 wine tasting in the famous Constantia Valley (can be changed to something else), on-the-day-customisation and full flexibility

Rate excludes: Lunch and gratuity

Please contact us to request a quote.

*NOTE: For last minute bookings, special requests or large groups, please contact us directly at +27 79 607 1978 or [email protected]

What Is Sideways Approved?

Explore Sideways has left no path unexplored on the journey to offering our guests a truly unforgettable immersive experience. Each one of our tours and experiences is the result of meticulous planning and research and every one of our activities has been handpicked and personally tested by our very own inhouse team of expert local Experience Curators.

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