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.

Carman Pillay

General Manager

Carman is the General Manager at Explore Sideways and is responsible for driving the  growth of the company and for managing the overall day to day. Having worked in the events industry, climbed the ladder in digital marketing world, and then having spent time business consulting and working on his own projects, he brings entrepreneurial fervor, and an eye for innovation in every aspect of what Explore Sideways does. Carman pairs his passion for travel, startups and problem solving with a love for the unexplored, and believes in experiencing life to its fullest – from trying new things, to eating new foods and sharing it with others along the way.

Ian Haggie

Business Development

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.

Michelle Juni

Experience Coordinator

Michelle is the Experience Coordinator at Explore Sideways and is responsible for running all the operations and logistics behind each and every Sideways experience.  Having spent a number of years living in Sao Paulo, Brazil, she moved to Cape Town and immediately fell in love with the Mother City and her Cape Wines. With a solid background of 4 years in market and consumer research and then a number of years consulting in the travel industry, she is well acquainted with the value of an incredible customer experience and what it’s like to be in the customer’s shoes. Michelle blends her love for people, wine, and travel by not just putting together experiences, but by trying to truly make people’s travel dreams come true.
Brittany Hawkins_explore sideways ceo

Brittany Hawkins


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.

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.