Explore Sideways
Explore Sideways
5
City ToursPrivate ToursFood ToursWine Tours & Tastings Day Trips
9:00 AM - 12:00 PM
Monday
8:30 AM - 6:00 PM
Tuesday
8:30 AM - 6:00 PM
Wednesday
8:30 AM - 6:00 PM
Thursday
8:30 AM - 6:00 PM
Friday
8:30 AM - 6:00 PM
Saturday
9:00 AM - 12:00 PM
Sunday
9:00 AM - 12:00 PM
Full view
About
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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Detailed Reviews: Reviews order informed by descriptiveness of user-identified themes such as cleanliness, atmosphere, general tips and location information.
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5.0
132 reviews
Excellent
129
Very good
2
Average
0
Poor
0
Terrible
1
Arnie J
Hampton, NH44 contributions
Dec 2022 • Couples
Ryan was the best!! Easy to talk too and very flexible to our wine tour expectations. I would recommend him for anyone visiting Capetown.
Written 3 January 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Tara
Hoboken, NJ5 contributions
Aug 2022
We had an awesome experience hiking Lion's Head with our guide, Matt. He was super knowledgeable, kind and helpful. Would highly recommend!
Written 14 November 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Shannon Thieneman
1 contribution
May 2022 • Friends
Had a fabulous wine tour with Ryan! He went above and beyond for our group of friends during the wine tour. He was very knowledgeable, had a great personality and arranged everything for our day trip. He even handle an emergency for one couple in our group during the tour. Cannot wait to schedule another tour with Ryan. The scenery is spectacular and the wines were fabulous!!
Written 17 May 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
LKC
1 contribution
Feb 2022
Our experience with Ryan was incredible! We had an amazing time exploring for 4 days. Ryan knew everything about the city and we had a great time together along the way. I would highly recommend if you are planning a trip to Cape Town!
Written 11 May 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Kelly Lucchesi
New York City, NY1 contribution
Feb 2022 • Couples
Our experience with Ryan at explore sideways was EXCEPTIONAL! We toured with him for three days and wish we could have brought him along to our next destination. He was incredibly knowledgeable, took us to both local spots and “must hit’s”. We spoke about everything from the language, the history, the cuisine, the animals, and the land. He is also extremely flexible- he can mold the perfect trip to your interests, as he did for us. We will continue to stay in touch with Ryan far past our honeymoon :) thanks again!!
Written 10 February 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Tenutae
117 contributions
Oct 2021 • Couples
Total bliss! We were taken so good care of by Ryan, that we got really spoiled. His knowledge about the area and the History was impressive and enlightening. We liked his relaxed style, always adapting to our needs and wants. Highly recommended.
Written 26 October 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
lori g
6 contributions
Aug 2021 • Family
Best time with Ryan!
so our travel agent arranged for my family’s 3 days of private cape town touring with ryan from explore sideways, and we had the best time! we weren’t easy - we needed someone flexible, good humored when we were perpetually late, full of information but not stuffy, talkative (hubby, 21 and 25 year old sons and me all talk a lot) good sense of humor and accommodating “off the beaten track” with us.
Explore Sideways put together a great itinerary and sent us Ryan who was all this and more, he exceeded the challenge of my family! we had a great time with Ryan seeing the cape of good hope on e-bikes, saw the winery countryside on ATVs (quads), hung with the cool people at a trendy place in Camps Bay and Ryan kept us endlessly amused and laughing during the long drives. he was knowledgeable, fun, and flexible, even changing the itinerary to best match the weather patterns, we strongly recommend Ryan and Explore Sideways for a great time in cape town!!
ps hope folks start returning to south africa vacationing, we felt perfectly safe everywhere we went with their covid protocols.
so our travel agent arranged for my family’s 3 days of private cape town touring with ryan from explore sideways, and we had the best time! we weren’t easy - we needed someone flexible, good humored when we were perpetually late, full of information but not stuffy, talkative (hubby, 21 and 25 year old sons and me all talk a lot) good sense of humor and accommodating “off the beaten track” with us.
Explore Sideways put together a great itinerary and sent us Ryan who was all this and more, he exceeded the challenge of my family! we had a great time with Ryan seeing the cape of good hope on e-bikes, saw the winery countryside on ATVs (quads), hung with the cool people at a trendy place in Camps Bay and Ryan kept us endlessly amused and laughing during the long drives. he was knowledgeable, fun, and flexible, even changing the itinerary to best match the weather patterns, we strongly recommend Ryan and Explore Sideways for a great time in cape town!!
ps hope folks start returning to south africa vacationing, we felt perfectly safe everywhere we went with their covid protocols.
Written 25 August 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Tom D
New York City, NY14 contributions
May 2021
Eon, our tour guide with Explore Sideways, literally made our honeymoon trip to Cape Town. He was a gracious, accommodating, informative, attentive, funny and entertaining guide. His comforting, approachable and good natured manner made us feel like we were visiting a friend from out of town. Further, his deep knowledge of wine and winemaking was unique and helpful on our trip to Stellenbosch. He was always punctual and organized a well thought out tour that maximized our short time (3 days) in Cape Town. We can't recommend Eon & Explore Sideways enough.
Written 22 June 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Papesfamily
Mount Kisco, NY2 contributions
Jun 2021
Wow did we have an awesome experience with our guide Ryan, who took us all over Cape Town with unrivaled expertise over 3 full days! He showed us what we wanted to see, helped us understand what we should see that wasn't on our list, while also loading us up with answers to our many questions and recommendations from end to end.
Written 21 June 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Ashley P
1 contribution
May 2021
Because of COVID, our anniversary trip to South Africa was delayed. The trip, however, was definitely worth the wait! We spent several days touring Cape Town with our wonderful guide, Ryan. He took us to every single spot we were hoping to see while still incorporating smaller, more local spots. Ryan was able to change our schedule around to fit the most into our days, while never making anything feel rushed. He also changed around our schedule based on the weather forecast, which worked out perfectly! It was obvious how much Ryan loves South Africa (specifically Cape Town) and his enthusiasm was infectious. We are already looking forward to planning a trip back!
Written 26 May 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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