Cape Town Wine Tours &

Private Luxury Tours in 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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Specialist Guides

Guest Favourites

Learn more about our highest rated tours and experiences

Franschhoek View
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 Bucket List

Best of the Cape Winelands Tour (Stellenbosch & Franschhoek)

Discover the breathtakingly beautiful views and vistas of Franschhoek and the world class-wines of Stellenbosch during this luxury, private tour.

From R 2,243 / person
  • Full Day Private Tour
Helicopter Tours
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 Wine & Food

Cape Winelands Helicopter Tour

Take to the skies and explore the winelands in your private helicopter with a personal wine specialist guide. This exclusive curated experience showcases the absolute best of the Cape Winelands.

From R 8,079 / person
  • Full Day Private Tour
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 Wine & Food

Hidden Gems Wine Tour

This exclusive tour will take you to the wine estates less well known, but producing some of the most sought-after wines the region has to offer.

From R 1,945 / 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.
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Wine & Food
Indulge your palate with fine wines and world-class cuisines.
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Art & Culture
Rich art experiences and local culture immersions.
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Adventure & Wellness
Fun encounters and pampered sunsets.
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Family-Friendly
Adventures and fun for the whole family.
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Romantic Getaways
The perfect romantic escapes just for two.
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What We Offer

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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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