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Address: Woodstock 7915, South Africa
Phone Number:
+27 79 607 1978
Recommended length of visit: More than 3 hours

Explore Sideways is the premiere luxury provider of wine experiences in the...

Explore Sideways is the premiere luxury provider of wine experiences in the Western Cape.

We specialize in highly curated, private tours, offering intimate access to the most amazing wines and estates

Wineries know and love us which means they offer tastings and experiences exclusively for Sideways guests.

All tastings and activities less lunch are included in the cost and are pre-arranged to perfection.

Each fully accredited guide is only selected once the tour is booked, ensuring a perfect match to both the person and the experience. We source each guide individually so are able to offer bespoke, luxury experiences with guides that are passionate, knowledgable and experienced.

Day tours take you off the beaten path and into the hidden gems of Franschhoek, Stellenbosch, Hemel-en-Aarde, Paarl, Elgin, Constantia and many of the other lesser known wine regions.

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Book In Advance
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Private Half Day Wine Tour from Cape Town
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Whales and Wine Day Tour from Cape Town
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Cape Town History Tour

TripAdvisor Reviewer Highlights

Read all 63 reviews
Visitor rating
  • 61
  • 1
    Very good
  • 0
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  • 1
Justin was exceptional

Our guide, Justin, took us round a day long tour of various wine tastings. He was excellent. Affable, a really nice chap, and extremely knowledgeable about wine, the wine regions... read more

Reviewed 4 weeks ago
Solihull, United Kingdom
via mobile
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63 Reviews from our TripAdvisor Community

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Showing 63: English reviews
Solihull, United Kingdom
Level Contributor
3 reviews
common_n_attraction_reviews_1bd8 1 helpful vote
Reviewed 4 weeks ago via mobile

Our guide, Justin, took us round a day long tour of various wine tastings. He was excellent. Affable, a really nice chap, and extremely knowledgeable about wine, the wine regions and South Africa in general, and offered insight into the European wine market from his own experience of living there. This, and the various different tastings he took us to,... More 

Thank Zemross
JolizeA, Manager at Explore Sideways, responded to this review

Hi Matt and Emma, Firstly congratulations on your nuptials. Hope you are having fantastic honeymoon here in Cape Town. I am so happy to hear you had a great time with Justin and that you enjoined the Winelands! Justin's knowledge is fantastic and you could ask for a better wine guide. Thank you for the review and enjoy the rest... More 

St. Helena, California
1 review
Reviewed 4 weeks ago

Henri took us on an amazing trip around the "No Drive" zone of Table Mountain. The views are breathtaking... and what do you know... Wine and food at the top! Henri was very knowledgeable about the local flora & fauna and was able to guide an adventure on both a micro and macro level. Wines were tasty, and the whole... More 

Thank brandenmcdonald
Hawkbritt, General Manager at Explore Sideways, responded to this review

Hi Branden, I'm so glad to hear you had a phenomenal time going offroad on Table Mountain! This is quite a unique way to experience a bucket list aspect of the Cape. Henri is very knowledgeable so we're happy to hear he was able to share his passions. We look forward to seeing you on your next trip to Cape... More 

Washington DC, District of Columbia
Level Contributor
24 reviews
9 attraction reviews
common_n_attraction_reviews_1bd8 13 helpful votes
Reviewed 15 April 2017

Had a great time, Explore Sideways gets you VIP treatment at the area's wineries. Our guide Eon was an expert and made our day tour fun and seamless and every representative at each winery was an expert in their field and their product. We did the Constantia day tour, and one suggestion I would make for other travellers is to... More 

Thank K C
Hawkbritt, General Manager at Explore Sideways, responded to this review

I'm so glad to hear you got to see a VIP view of the Constantia winelands! Eon is truly passionate about wine and has done multiple harvests both in South Africa as well as other countries so he's always excited to share his knowledge. Please let us know next time you're in town so we can share more off the... More 

London, United Kingdom
Level Contributor
60 reviews
19 attraction reviews
common_n_attraction_reviews_1bd8 59 helpful votes
Reviewed 26 March 2017

I organised a corporate day out in the wine region with Explore Sideways and they were an absolutely pleasure to work with. Trying to organise something from overseas (I am based in Australia) can be difficult, but these guys were an absolute dream to work with. Even when we had last minute changes, there was no problem changing everything around.... More 

Thank Natasha W
JolizeA, Manager at Explore Sideways, responded to this review

Hi Natasha, It was such a pleasure to work with you and this exciting itinerary, not to mention fun! Thank you for allowing us to host your group and show them the Winelands, and some of my favourite places. Hope to welcome you back soon and enjoy some great wines together! Warm regards Jolize More 

Fort Lauderdale, Florida
2 reviews
common_n_attraction_reviews_1bd8 4 helpful votes
Reviewed 24 March 2017

Being an expat living here in Cape Town, I of course have to show off my new home to my family. Our Experience Sideways tour of Stellenbosch was a perfect way to spend a day learning about wine with our very knowledgeable guide, Karen. We were able to get to 4 beautiful and unique vineyards, have a stunning lunch, and... More 

2 Thank MMK2008
JolizeA, Manager at Explore Sideways, responded to this review

Hi Meg, Thank you for the great review! How interesting that 4 vineyards in the same region can be so different and unique, but special in their own way. We look forward to showing your parents around Cape Town this week on the History Tour. Warmest regards Jolize More 

Cape Town, South Africa
1 review
Reviewed 14 March 2017

What a spot! How exploring Table Mountain through sideways... Henri, our guide, was a lovely host, as the 2 rangers who were escorting us all along the way. The wine was good, and we appreciate to be served with proper cutlery & platlery and the napkin in tissue... "The best picnic ever!" Thank you!

Thank sophieagostini
JolizeA, Manager at Explore Sideways, responded to this review

Hello Sophie! So glad you and your family enjoyed the Table Mountain Safari, it was our pleasure to host you. Hope you enjoy the rest of your stay. Warm regards Jolize More 

Chapel Hill, North Carolina
Level Contributor
135 reviews
31 attraction reviews
common_n_attraction_reviews_1bd8 76 helpful votes
Reviewed 12 March 2017

The head of the agency and the staff are very thoughtful and knowledgeable and worked with me to create the best organized tour for a couple i have had in years. We explored old and new wine areas of the Stellenbosh region. She booked all the great restaurants we wanted to visit, was flexible to get me to the vineyards... More 

Thank barry p
JolizeA, Manager at Explore Sideways, responded to this review

Dearest Barry, It really was a pleasure to assist with your trip, and it is great to work with a client who has a clear idea of their preferences. Cape Town has so much to offer and we want to make sure each guest receive the experience matched best to their interests. And yes Charlene is great and super knowledgeable!... More 

London, United Kingdom
Level Contributor
49 reviews
4 attraction reviews
common_n_attraction_reviews_1bd8 25 helpful votes
Reviewed 7 March 2017

This has to be one of the best tours I've ever done. Henri, our guide was so helpful and knowledgeable and the experience was nothing less than excellent throughout. If you are looking for something unusual to do in Cape Town, you'll find this difficult to beat. Highly recommended!

Thank petersitges
JolizeA, Manager at Explore Sideways, responded to this review

Hi Peter, We are delighted to hear you had a great time. How fabulous are the views! And Henri is the best host, so glad you enjoyed the experience and hope to welcome you back soon. Warm regards Jolize More 

1 review
Reviewed 13 February 2017

I used Explore Sideways to book a wine tour on Table Mountain. I was impressed by the speed of their service as we booked the tour the night before the morning we wanted to leave. The actual wine tour on Table Mountain was great - Henri is the guide and he was charming and attentive. I am a Cape Town... More 

Thank Reyburn H
Ian H, Director of Sales at Explore Sideways, responded to this review

Dear Reyburn Thanks for the review! We love getting feedback so thanks for sharing. Henri is great and as you say, charming and attentive and he certainly know's his way around the mountain. We're working with him to introduce a handful of new trails with other viewpoints so make sure to check back in a month or two for new... More 

1 review
Reviewed 7 February 2017

An off road driving tour of Table Mountain park with a picnic and wine tasting. Henri, our guide, was great we felt safe and very well looked after. He was a mine of information and infectiously passionate about the park. We felt truly privileged to be driven to spots that the public can usually not get to or would take... More 

Thank Daniel M
Hawkbritt, General Manager at Explore Sideways, responded to this review

Hi Dan, I'm so happy to hear you had such a fantastic time! This is one of our favourite and most exclusive experiences that enables you to experience Table Mountain unlike ever before. Henri is the absolute best (and only) 4x4 guide for the Mountain and I'm glad he looked after you properly. Thanks so much for choosing us and... More 

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  • Will you pick up and drop off at my hotel?
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