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Patagonia: The Ultimate Food, Wine & Wilderness Adventure

Join us on a rare opportunity to fully disconnect from the outside world and immerse yourself in food, wine and wilderness with a world-renowned chef.

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  • 6-Night Private Experience
View of Stellenbosch
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South Africa: A Journey Inspired by Old Vine Heritage

Ever had a glass of wine made from a 35-year-old vine? How about 50 years old? Go on a journey of South Africa’s Old Vine heritage as we fly you to some of the country’s most sought-after wine estates.

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  • Full-Day Private Experience
People drinking wine in the Okanagan Valley Canada
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Okanagan Valley: A Wine Lover’s Dream in Canada

Set along a series of lakes with unbelievable views, the Okanagan Valley in Canada is a wine lover’s dream.  On this iconic, full-day experience, you’ll be visiting award-winning wineries, having lunch right in a vineyard and so much more.

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  • Full-Day Private Experience
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Portugal: Wine and Dine in the Douro Valley

A long-time destination for curious wine lovers, the Douro Valley in Portugal is the world’s oldest wine region. Explore centurion vines, dine with a Michelin Star chef and climb on board a private helicopter - the perfect day in the Douro.

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  • Full-Day Private Experience

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Tour Collections

Discover our portfolio of unique experiences

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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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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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Private Tours
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Curated Experiences
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Languages Available
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Specialist Guides