Private Luxury Experiences

in South Africa & Portugal

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

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 Bucket List

Best of the Cape Peninsula Tour

Enjoy a breathtaking journey around the Cape Peninsula and Cape Point and capture picture-perfect photos from every angle...'from the waves to the winelands'

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  • Full Day Private Tour
Constantia Helicopter Wine Tour
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 Wine & Food

4×4 Wine Tasting & Helicopter Flight

Take to the skies for a scenic helicopter flight over the Cape Peninsula before touching down at a historic Constantia estate for a unique wine tasting experience.

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  • 2-3 Hours
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 Wine & Food

Miradouro: The Picture Perfect Itinerary

From iconic and modern to classic and traditional. This is the ultimate itinerary to get the perfect shot and taste some of the best wines of the Douro valley.

From / 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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Can’t find what you are looking for?

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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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