Explore Sideways
Explore Sideways
5
City ToursPrivate ToursFood ToursWine Tours & Tastings Day Trips
8:30 AM - 6:00 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.
Similar Experiences
Travellers talk about
Contribute
Most Recent: Reviews ordered by most recent publish date in descending order.
Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as waiting time, length of visit, general tips, and location information.
Popular mentions
5.0
134 reviews
Excellent
131
Very good
2
Average
0
Poor
0
Terrible
1
lori g
10 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.
Rodrigo Moran
7 contributions
Jan 2020
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.
Would do it all over again.
Written 27 January 2020
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.
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.
pix31000
Vancouver, Canada11 contributions
Aug 2015 • Friends
Looking for something different to do this time in Cape Town, I happened to find Explore Sideways when I was searching for Zip Lining tours. I emailed them and they were very helpful providing the details of different tours. I ended up doing the Winelands Outdoor Adventure Tour. It was a bit pricy if there are only 1 or 2 people doing the tour, but the experience was unique compared to some other tours. Riding horse and then a Segway in Cape wineland was definitely something memorable. It would be better if cheese was provided during wine tasting. But it was a great fun day trip overall.
Written 26 January 2016
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.
Thanks so much for your nice words. We're very glad you enjoyed your Winelands Outdoor Adventure Tour! We're always on the lookout for the most exciting and unusual experiences in the winelands so it's great to hear the positive feedback. We'll look into some wineries that might offer a nice cheese pairing with the tasting as well.
We hope to see you again in the future!
Written 27 January 2016
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Raj_Me33
Washington DC, DC37 contributions
Mar 2018 • Couples
We only had 2 days in Cape Town so we wanted to be sure and see as much as we could. Jolize from Explore Sideways helped us build a great itinerary based on our interests. Pim met us at our hotel shortly after we arrived and the next two days were a great adventure. Day 1 we toured sights around Cape Town, and on Day 2 did the Cape Peninsula Tour. He is a wonderful guide and we felt like we were touring with a friend. We learned so much about the area and enjoyed our conversations. The tour ended with an expert wine tasting at Constantia, which is such a beautiful winery. My husband had left his phone in Pim's car---and we had already left Cape Town for the winelands. Pim made a special trip to make sure we got the phone back before we flew out. We highly recommend Explore Sideways--be sure to request Pim!
Written 28 March 2018
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.
Dear Sarva,
Thank you so much for the amazing feedback. I am so glad we we able to fit everything in on your list! Pim is just great and will bend over backwards for our guests, who all become friends by the end of the trip.
We look forward to welcoming you back soon!.
Warm regards
Jolize
Written 1 April 2018
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Adam F
Perth17 contributions
Feb 2016 • Couples
Fantastic tour of Franschhoek with multiple top quality wine tastings (too many to remember!!) and delicious food combined with breathtaking scenery. Anne-Marie provided a real personalised service and we learnt and saw things no conventional wine tour would have covered. Thoroughly recommended and great value for money.
Written 17 February 2016
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.
Hi Adam,
I'm so glad to hear you had such a spectacular time! We really appreciate the feedback and always love when people share our passion for food and wine. Please come and visit again soon. There are so many places still to see!
Written 18 February 2016
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
annedavids
Santa Clara, CA6 contributions
Oct 2015 • Couples
It was wonderful to have someone pick me up, give us a great tour & take us to the wineries . Our driver was a great type guide, with plenty of background information for us. The only thing that could make this better was more wineries as an option. I would rather get a quick lunch and go to another winery in the day. We typically had 3 wineries, but could have time for a couple more. The driving tours were great, and I would definitely use Sideways again!
Written 22 January 2016
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.
No questions have been asked about this experience