Explore Sideways was founded by proud locals on a mission to show the world the very best that Cape Town has to offer. Through years of personal exploration and experience as passionate food and wine lovers, the Explore Sideways team have curated a collection of the most delicious, immersive and memorable itineraries and experiences in the Cape – an insider’s map of the hidden gems, the unmarked cellar doors and the most dynamic local culinary experiences, all topped off with a dash of adventure.

Whether you’re after a sunset horse ride through picturesque vineyards, an adrenaline-filled zipline through majestic ravines or simply looking for that perfect bottle of wine to take home after a day exploring the winelands – we know just where to find it. Our team of expert consultants and specialist guides will curate an unforgettable private experience customized to your exact interests and preferences. You’ll come away relaxed, inspired and thoroughly entertained.

What it means to explore sideways

  • Our team of food, wine, and cultural insiders goes off the beaten track to ensure highly curated experiences unlike any other.
  • All tastings and listed activities are included in the cost and are pre-arranged to perfection.
  • Every experience handcrafted with integrity, passion, and expertise.
  • Each fully accredited guide is only selected once the tour is booked, ensuring a perfect match for both the person and the experience.




Get in TOUCH

Email info@exploresideways.com
Phone +27 (079) 6071978 – Also Whatsapp us!
Skype ExploreSideways

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Latest Testimonials

It has to be one of the best tours I’ve ever done. If you are looking for something unusual to do in Cape Town you’ll find this difficult to beat. Highly recommended!

Peter S.

Latest Testimonials

It has to be one of the best tours I’ve ever done. If you are looking for something unusual to do in Cape Town you’ll find this difficult to beat.
Highly recommended!

Peter S.


Brittany Hawkins_explore sideways ceo

Brittany Hawkins

Chief Experience Officer

Brittany is the Chief Executive and Experience Officer at Explore Sideways, where she oversees the company vision, strategy, marketing and management. Brittany’s passion for food and wine began in her hometown, Napa Valley, California, where she grew up immersed in the wine industry. After receiving a degree from DePauw University, she began her career in Silicon Valley in the advertising and marketing industries. She then co-founded Swirl it!, the first taste-based wine recommendation app which was featured in the Apple App Store and TechCrunch. Brittany moved to Cape Town 3 years ago where she launched Explore Sideways and has since been able to marry her interests in food, wine, travel and tech to create transformative experiences around the world.

Jolize Aschmann

Experience Specialist

Jolize oversees every immersive experience offered Explore Sideways. Whether it’s outdoor adventures, local cultural experiences or insider access to phenomenal food and wine, she is the first to know about anything unique and interesting happening in the Western Cape. Prior to Explore Sideways, she spent 11 years in the events industry for major brands and magazines where she developed the ability to make every Explore Sideways experience into a unique and exciting event. Jolize is a native of Cape Town and went on to spend 6 years abroad in London, giving her a unique appreciation for being immersed in a new city and culture.
Ingrid-mpofu_explore sideways

Ingrid Mpofu

Experience Specialist

Ingrid assists with the logistical side of the experiences offered Explore Sideways. She spent 8 years in the Adventure Education and Recreation industry in Johannesburg, working as the Lead Facilitator and Trainer for various campsites with regards to outdoor education. After working for a year in the hospitality industry in the UK as well as a summer camp season in the USA, she moved down to Cape Town and discovered the tourism industry & of course – wine! Now a qualified tourist guide for the Western Cape, she enjoys broadening her knowledge as to what South Africa has to offer and creating those once-in-a-lifetime experiences for anyone visiting Cape Town.

Ian Haggie

Experience Specialist

Ian heads up business development at Explore Sideways, overseeing corporate partnerships and ensuring continued business growth and positive client relationships. Ian’s passion for food, wine and travel began in Johannesburg where he sold fine wine to the hospitality and restaurant trade. It was there that he developed an appreciation for cabernet sauvignon and pinot noir, his two favourite varietals. His passion for epicurean adventures has taken him around the world and introduced him to incredible food, lifelong friends and world class wines. He has experienced the full cycle of production – from working in the vineyards, to cellar work and vinification and into sales and distribution. He now aims to share his passion for great food, wine and travel with people that are visiting South Africa.

Joshin Raghubar


Joshin is the founder of Explore Sideways, serving on the Board of Directors and the Executive staff. With more than a decade of Pan-African experience in the media, marketing, technology and telecommunications sectors, Joshin is a seasoned entrepreneur and innovator in the South African startup and tech scenes. Ambition and innovation are the two key driving forces behind Joshin’s success to date. He also intrinsically possesses a passion to create value by weaving together creative ideas, relationships, emerging trends, talented people, entrepreneurial spirit and a commitment to action. Joshin is a fellow of the Africa Leadership Initiative and the Aspen Institute’s Global Leaders Network. He is a 2016 Yale Greenburg World Fellow.

Pauline Brown

Board Advisor

For more than 25 years, Pauline Brown has acquired, built and led global luxury brands. In 2016, she joined the faculty of the Harvard Business School, where she introduced a new interdisciplinary course for graduate students, called “The Business of Aesthetics.” Pauline is currently taking a sabbatical from teaching in order to write a book on the power of aesthetic intelligence. Pauline also currently hosts a weekly lifestyle show on SiriusXM, called “Tastemakers.” Prior to entering media and academia, Pauline was the Chairman of North America for the world’s leading luxury goods company, LVMH Moët Hennessy Louis Vuitton, where she provided regional leadership for 70 brands.