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.

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.

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.
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.
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.
Marketing & Digital Manager
Jenna is our Marketing & Digital Manager and resident content guru. With an e-commerce travel background and a love for wine, food, and travel itself, she brings with her a passion to ensure that customers have the best Sideways experience from start to finish.
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.
Who will be joining next?
Feel like you have what it takes to join our team? Send us an e-mail at [email protected]

Our Partners

We partner with leading brands in international travel