Explore Sideways is the leader in immersive food, wine, culture and adventure tours
Get off the beaten track with unique, handcrafted experiences in Cape Town and surrounds allowing you insider access, exclusive activities, personalised curation and a private, specialist guide.
- Unique full day and half day tours of Cape Town and the winelands
- All tours are private with your choice of 12 language guides (upon request)
- Pickup and drop-off at your accommodation in and around Cape Town
- Choose from over 20 curated tours or let us tailor-make the perfect experience for you
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.
- Each fully accredited guide is only selected once the tour is booked, ensuring a perfect match to both the person and the experience.
- Every experience handcrafted with integrity, passion and expertise.
- We believe that travel is about people and we always make sure to add a personal touch.
Get in Touch
We’re happy to answer any questions or put together a tailor-made itinerary just for you. You might just be amazed what we can come up with!
Mobile: +27 (079) 6071978 – Also Whatsapp us!
Landline: +27 (021) 2016424
Meet the Sideways Team
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.
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 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.
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.
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.