Explore Sideways

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Explore Sideways Explore Sideways is a luxury travel company specialising in exclusive, private tours and experiences to the curious and discerning traveller.
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Thank you @seaskyvillas for hosting @gabrielmornelas for our Cape Town recce for @itsonthepass. Seasky embodies a massively important side of the hospitality industry: creating beautifully appointed and well designed homes for travellers to feel they can explore and adventure around this beautiful city from a hub of luxury, comfort and style. Their villas are carefully selected, gracefully decorated, and most importantly manned by kind, thoughtful and attentive team members. The views are incredible - and a gentle reminder of how lucky we are to be surrounded by such impressive nature! 🌊🌿🌞 We sat down with Seasky Villas owner & founder @estamarita , to hear more about her thoughts on operating her business in South Africa, her hopes and excitements for Cape Town’s future and of course her lovely team. We thank you for your time and your hospitality! We look forward to having many guests enjoy Esta-Marita & her team’s special gift for hospitality! As we like to say: this has been Sideways Approved! Reach out to book your next exploration of Cape Town ✨ @simon_watson_photo #seaskyvillas #capetownhospitality #villadesign #campsbay #capetownliving #capetowntravel #sidewaysapproved #onthepass

Thank you @anthony_hamilton_russell for hosting us! Hamilton Russell, founded by Anthony’s father, in 1975, after an exhaustive search for the most southerly land to grow vines which would flourish and hone a distinctive cool-climate wines. The vineyard pioneered wine-making in the Hemel-en-Aarde valley. Meaning ‘Heaven and Earth’ in old Dutch & Afrikaans - a drive through this stunning area and a visit to this farm makes it very clear where the name came from! Hamilton Russell’s wines, notably their Chardonnay & Pinot Noir varietals, are world renowned and highly praised. What really stood out for us was Anthony’s warm hosting style, sense of humour, humility & ability to impart knowledge in such a meaningful way! We are grateful for your time and look forward to returning. @gabrielmornelas @itsonthepass

Part 1: The Cape Winelands 👌 🍇 @africaskyrunners pilot & owner Mike White took us on the most wonderful trip into the Karoo desert. We are so excited to be including Mike’s wonderful plane, nicknamed “KYD” (find out why in Part 2!), and his experiences in our catalogue. Stay tuned for more exciting adventures! We can most definitely say this experience is #SidewaysApproved 🙌 #charterflight #byair #capewinelands #winecountry #travellife #travel #capetown #capetowntravel #southafrica #luxurytravel #discoversouthafrica

These colourful Edoardo Villa sculptures pop up all over the grounds @steenbergfarm - brining whimsy & charm to the estate. Villa, born in Italy, rose to be one of South Africa’s most prolific sculptors. Creating over 1000 pieces, Villa rejects the traditional, conservative approach. Moved by the more figurative style of African sculpture, Edoardo’s anti-establishment is felt through his work. Villa ended up in South Africa after being captured in Egypt while serving his conscription time in the Italian Military. Villa, after his imprisonment in Zonderwater (an internment camp near Pretoria), decides to stay in South Africa and exhibits his first works, at the Johannesburg Library within the same year - 1947. Let us know what artist’s@story or work you are currently enjoying in the comments 💬 Explore Sideways has a passion for the arts. We are fortunate to work closely with notable experts who meet our guests and navigate the wonderful world of Art in South Africa during their travels here. Reach out to the team to see what wonderful explorations we can create for you or your guests 🙌 #edoardovilla #sculpture #gardenart #southafricanart #steenberg #constantia #artlover #wine #winecountry #winelands #southafricantourism #capetown #capetownart #artinthegarden #sculpture_art

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Our Story

Exploring Sideways is all about getting off the beaten track and experiencing destinations like never before. The bespoke collection of private tours are outfitted for discerning and curious travellers seeking unique experiences and unforgettable moments, rather than generic, “one-size-fits-all” tours. Whether you’re a sip-savvy connoisseur seeking out the best of the best in wine country or a family looking for fun and adventure, we’ve got a spectrum of activities, sights and tastes no matter your interests.

Our passionate and professional guides are what truly complete the perfect Sideways experience. We match the expertise and personality of each expert guide to every single tour, with additional on-the-day customisation that will match your mood, your pace and even your most specific requests.

We are happy to provide any and all recommendations. Please email us at [email protected] to start exploring!