Cape Town Wine Tours &

Private Luxury Immersive Tours South Africa

From soil to glass the world of wine elevates every experience. Our expert team have curated the very best specialist guides, private tours and experiences for the discerning and curious traveller. Choose private tours from our collections, or let us help design a tailor-made experience for you.

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Private Tours
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Curated Experiences
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Languages Available
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Specialist Guides

Guest Favourites

Learn more about our highest rated tours and experiences

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 Wine & Food

Ultimate Franschhoek Foodie & Wine Tour

Taste excellent food and superb wine from some of the best estates in South Africa’s culinary capital, Franschhoek.

From R 2,616 / person
  • Full Day Private Tour
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 Wine & Food

Family Winelands Adventure

Wine tasting and fun for parents and children. Animal encounters, grape juice tastings, jungle gyms and play areas. A great day out for the whole family.

From R 1,898 / person
  • Full Day Private Tour
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 Bucket List

Curated Cape Town City Tour

Explore the majestic city of Cape Town and discover it's hidden gems while ticking off the best of your bucket list

From R 1,956 / person
  • Full Day Private Tour

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“Amazing team that made my birthday trip with friends to the wine country unforgettable. They managed to negotiate for a wine farm to open just for us for an incredible lunch (De Meye), and at another, organized a unique wine and food pairing.”

Alice, New York

"We had limited time for leisure on a business trip to Cape Town and enjoyed our 4x4 wine safari with Henri. Magnificent views and a fun time. We would highly recommend Explore Sideways to others looking for a unique experience in the "Mother City".

Xavier, New Haven

"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."

Peter, London

Tour Collections

Discover our portfolio of unique experiences

Bucket List
Tick off your list with a unique Sideways twist.
Explore
Wine & Food
Indulge your palate with fine wines and world-class cuisines.
Explore
Art & Culture
Rich art experiences and local culture immersions.
Explore
Adventure & Wellness
Fun encounters and pampered sunsets.
Explore
Family-Friendly
Adventures and fun for the whole family.
Explore
Romantic Getaways
The perfect romantic escapes just for two.
Explore

Can’t find what you are looking for?

Speak to an expert on +27 79 607 1978 about creating your own unique tour itinerary or

What We Offer

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Get Inspired. Go Explore.

Read our latest insider guides before planning your next experience

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Why Book With Us

PRIVATE TOURS & EXPERIENCES
All our tours & experiences are provided in a private vehicle & with your own personal guide.
SPECIALIST GUIDES
All our guides are specialists in their respective fields with years of valuable experience & knowledge.
SIDEWAYS APPROVED
Every one of our tours & experiences has been curated & approved by our team of local experts.
FLEXIBLE & PERSONALISED
All our tours are flexible & can be tailored to suit your unique personal preference & taste.

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