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.

Private Tours
Curated Experiences
Languages Available
Specialist Guides

Guest Favourites

Learn more about our highest rated tours and experiences

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
Quinta do Popa
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Wine & Food

Hidden Gems of the Douro Valley

From €190 / person Overview [Full Day Private Tour] Explore

From R 8,950 / person
  • Full Day Private 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

Tour Collections

Discover our portfolio of unique experiences

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

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

Learn more about our tours and experiences

Private, Curated Tours
Unique Add-Ons
Design Your Tour

Get Inspired. Go Explore.

Read our latest insider guides before planning your next experience

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The Best Restaurants In Porto

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Wines To Try In Portugal

Wines To Try In Portugal

Portugal, a small but soulful country, has so much to offer its visitors. In recent years, the nation has seen a massive influx...

Why Book With Us

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

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