Why Explore Sideways?

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 this side of the equator. We offer the curious explorer an insider’s map to all the hidden gems, 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 where to find it. Our team of expert consultants and specialist guides will curate an unforgettable private experience customised to your exact interests and preferences. You’ll come away relaxed, inspired and thoroughly entertained.

Our Origins

It all started with a government initiative to increase international tourism to the Cape. Being passionate travellers ourselves, Sideways — as we were known back then — was founded by a group of like-minded explorers who took the company from a mobile app for travellers in its early stages to the full-service guest experience platform it is today.

Our initial contact with travellers brought to light the need for more personalised luxury travel experiences from the more curious and discerning. Since then, we’ve hosted more than 1,500 tours and experiences for guests and continue to redefine the art of travel as we welcome explorers from far and wide.

Use our website as your portal to the world of fine food, fine wine and the finest in authentic and immersive travel experiences when you embark the road less travelled with us.

Explore Sideways By Numbers

Private Tours
Curated Experiences
Happy Guests
Wine Tastings

Meet the Explore Sideways Team

Co-Founder & CEO
A seasoned entrepreneur with various successful startups under his belt, Joshin brings a wealth of experience, insights, creativity and expertise to the executive team. Through his vast exposure to media, marketing and technology, Joshin guides the Explore Sideways execution of world-class travel experiences for the sophisticated traveller.
Customer Acquisition & Growth Manager
Carman is responsible for driving the growth of the company while overseeing the day-to-day demands of running a busy luxury travel startup. He does this through a passion for people, a knack for problem-solving and an entrepreneurial fervour that sees him go beyond the extra mile for our clients and team members.
Guest Experience Manager
Michelle is our Guest Experience Manager who will go to every length to ensure your experience meets your expectations. She is responsible for running the logistical aspects behind the experiences that await you when you go exploring with us. After years in Brazil, Michelle moved to Cape Town, fell in love with the Mother City and the rest, as they say, is history.
Head of Product & Business Development
Ian heads up both business and product development at Explore Sideways. This involves establishing corporate partnerships while building human relationships that go beyond formality. An epicurean adventurer worth his salt, he has travelled around the world while being introduced to incredible food, fantastic people and world-class wines and now aims to share his passion with you.
For Brittany, growing up in the heart of the U.S wine and tech industries led to a degree from DePaul University, a career in Silicon Valley, co-foundership of an acclaimed wine recommendation app and, ultimately, a move to Cape Town where she continues to be a part of the executive team behind Explore Sideways.
Board Advisor
Over more than 25 years Pauline has acquired, built and led global luxury brands to success. Her tenure at the Harvard Business School saw her introduce a new interdisciplinary course for graduate students, called “The Business of Aesthetics.” Prior to entering media and academia, Pauline was the North American Chairman for the world’s leading luxury goods company, LVMH Louis Vuitton Moët Hennessy.

Our Partners

We partner with leading brands in international travel