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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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

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

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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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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Wines

What’s the Difference: MCC vs Champagne

May 14, 2019

Pop! Clink! Fizz! You know what time it is, right? Needless to say, there’s always a good reason to drink bubbly. It’s the...

Guides

The Explore Sideways Guides

May 9, 2019

For many travellers, venturing to a new city or country can be quite daunting. Not knowing where to go, what to do, or...

Wines

Top 10 South African Pinot Noirs

May 6, 2019

Guest Explorer: Venetia Wegelin Venetia finished her studies in Cape Town and headed back to Johannesburg in 2009 where she found herself looking...

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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Book a Private, Curated Tour

Redefine luxury with immersive private wine, food, art and culture tours and experiences.

Cape Town Wine Tours &

Private Luxury Tours in South Africa

Guest Favourites

Best of the Cape Winelands Tour (Stellenbosch & Franschhoek)

Cape Winelands Helicopter Tour

Hidden Gems Wine Tour

“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

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

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What’s the Difference: MCC vs Champagne

The Explore Sideways Guides

Top 10 South African Pinot Noirs

Why Book With Us

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Our Recommendations

Ultimate Franschhoek Foodie & Wine Tour

Family Winelands Adventure

Curated Cape Town City Tour

Book a Private, Curated Tour

Redefine luxury with immersive private wine, food, art and culture tours and experiences.

Cape Town Wine Tours &

Private Luxury Tours in South Africa

Guest Favourites

“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

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

Join the Explore Sideways Club

Get access to exclusive experiences, unique insider tips and expert travel recommendations

Get Inspired. Go Explore.

Why Book With Us

Featured In

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

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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