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Explore Sideways

Cape Town, South Africa
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About Explore Sideways
Exploring Sideways is all about getting off the beaten track and experiencing South Africa like never before. The bespoke collection of private day tours from Cape Town are outfitted for discerning and curious travellers seeking unique experiences and unforgettable moments, rather than generic, “one-size fits all” tours. Whether you’re a sip-savvy connoisseur seeking out the best of the South African Winelands or a family looking for fun and adventure, we’ve got a spectrum of activities, sights and tastes no matter your interests. Our passionate and professional guides are what truly complete the perfect Sideways experience. We match the expertise and personality of each expert guide to every single tour, with additional on-the-day customisation that will match your mood, your pace and even your most specific requests.
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Tours and Tickets by Explore Sideways

The Red Wine Lovers' Private Tour

Take a deep dive into the world of South African wine during this private, full-day, experience designed for wine lovers. Enjoy tastings at four of the Cape Region’s most celebrated wineries, savoring the latest vintages from producers like Meerlust, Kanonkop, Muratie, and Rust en Vrede. A private guide, tastings, and round-trip hotel transport by private vehicle are covered.
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1 day
from $314.59

Cape Town History Private Tour

Enjoy personalized attention and the benefit of a flexible itinerary on this private historical sightseeing tour of Cape Town. Go in-depth with the history of Cape Town through your guide's commentary during visits to the Company Gardens, the Slave Lodge, the District Six Museum, and the Bo-Kaap region. Finish up with a cellar tour of the Groot Constantia wine estate, including a chocolate and wine tasting. Enjoy the scenery on the route back to Cape Town via Camps Bay beach and Hout Bay.
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8 hours
from $302.29

Whales and Wine Private Day Tour (Seasonal)

Enjoy wide-open spaces, whales, and wine during this private, 10-hour, sightseeing and whale-watching excursion from Cape Town. Travel along the “whale route” between Cape Town and Hermanus, scouting for Southern right whales as they congregate, mate and calf just off-shore. In the afternoon, celebrate your adventure with included tastings at three local wineries.
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10 hours
from $263.68

Private Constantia Valley Wine Tour

Get to know the Constantia Valley's wine region on this full-day private tour from Cape Town. Through several winery visits and your dedicated guide's commentary, get to know the history of wine production in the the oldest wine region in the Southern Hemisphere. Highlights include visits, cellar tours, and tastings at Groot Constantia and the Eagles Nest Wine Estate, among others. Round-trip private transportation for you and your party from Cape Town hotels.
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8 hours
from $308.69

Marvelous MCC Bubbly and Art Tour

Discover the very best of both Stellenbosch and Franschhoek winelands as you sip on some of the best MCC South Africa has to offer. Learn about the rich history of the

Méthode Cap Classique and specifically, it’s South African context.
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8 hours
from $313.69
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Nastyona wrote a review Feb 2020
Moscow, Russia16 contributions7 helpful votes
This is a very nice, comfortable and tasty experience in Cape Town! Thanks a lot Explore Sideways who helped us to develop the itinerary (taking into account our preferences) for lunch reservation, wine tasting and cellar visit. Thank you for your patience (when we were asking much questions and proposing many different options) and thank you for reactivity to do final bookings! A separate thanks to Tim, our guide, who gave us enormous quantity of information, who replied all our questions concerning wine in SA and in France, and plenty other questions about South Africa everyday life.
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Date of experience: February 2020
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Joe eagle wrote a review Jan 2020
4 contributions
Booked a private tour through Sideways with white shark projects. Early pick up by Ryan van Reenen in his Jeep and had wonderful far ranging conversation from politics to surfing,wine to geology and many other topics on the 2.5 hour trip to Gansbaai. Beautiful calm day on arrival,lovely friendly crowd in Whitesharkprojects group, especially Tom our expert for the trip. Boat was ready,high speed to the cage and then fun of squeezing into wet suit-. We saw 3 big bronze whalers up close and enjoyed the magic of being in their space. No whites but are becoming increasingly unpredictable,that's nature. Lots of good info on shark protection and how endangered some of the species are,especially whites. Probably 40 mins in the water which was enough for this old fella. Happy ride home with Ryan and sure slept well that night. A definite must do if you love nature and the sea
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Date of experience: January 2020
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Rodrigo Moran wrote a review Jan 2020
1 contribution
I had a fantastic day with Fred, my jolly and incredibly knowledgeable tour guide. I felt like my tour was guided by an old friend that, with great passion, shared every single detail about his hometown. I asked many questions and for each one of them, a thoughtful answer. Would do it all over again.
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Date of experience: January 2020
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Manash D wrote a review Jan 2020
New Delhi, Delhi, India5 contributions4 helpful votes
Wow ! Cape Town : you are paradise on Earth. We had a family private tour from 25th December till 27th December in Cape Town as a part of our annual family vacation. Before that we had travelled Johannesburg almost 7 days. While compared between Cape Town and Johannesburg, Cape Town tour was amazing. Visit to Cape of Good Hope, Peninsula, Wine Valley, City Tour, Penguin Encounter.. wow what not . " Explore Sideways" had beautifully captured our travel itinerary and made sure we don't miss the prime attractions during our stay in Cape Town. Special thanks to our guide Ms. Felicity , who was too good as our company. She took extra efforts to arrange the things. of course she started communicating with us via " WhatsApp" before we landed Cape Town. She made it sure that we return home with a beautiful and memorable picture of Cape Town, its peoples and hospitality they offered. I give 5 on 5 to " Explore Sideways" team back in office and our tour guide Felicity. I strongly recommend " Explore Sideways" to all the tourists/families who wants to explore and enjoy to be part of a memorable HOLIDAY. Cheers !
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Date of experience: December 2019
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Shelly wrote a review Oct 2019
Los Angeles, California22 contributions2 helpful votes
We booked a private tour with Explore Sideways for a group of 5. We had Martin as a tour guide and he was brilliant! We were picked up in a very nice, roomy van in Cape Town. We drove to wineries in Stellenbosch and Franschhoek. I recommend letting the company know what you are interested in before going. I told them we wanted to focus on boutique wineries and try the reds and the MCC wines and we wanted a premium lunch option. Martin delivered! My highlights include Oldenburg Winery and Chef's Warehouse for lunch. These two experiences can't be surpassed in service and jubilation. We ended the day at Anthonij Rupert for a MCC tasting that was absolutely spectacular. If you are used to wine tours in the US (Napa region), this was a little different as Martin was our driver and our guide throughout the day. He was so nice and highly knowledgable and really kept us on time so we could enjoy the most of our day. I highly recommend using this company to see South Africa's wine country.
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Date of experience: October 2019
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