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

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.
Guest Experience Manager
Sherri-Lee is our Guest Experience Manager and brings a wealth of knowledge and expertise to the table. With 25 years in the tourism industry, including 8 years as a Guest Relations Officer on cruise liners and 12 years of leadership experience at CometoCapeTown, Sherri-Lee possesses a deep understanding of hospitality and a commitment to exceeding expectations.
Experience Coordinator
Moira is one of our South African Experience Coordinators and is passionate about taking care of our Guests. Moira has spent over 16 years in the hospitality and travel industry and 2019 she received her Concierge Golden Keys, she is the first woman in Cape Town and the first black woman in South Africa to have done so.
Experience Coordinator
Liesl serves as one of our South African Experience Coordinators, dedicated to ensuring exceptional guest experiences. With over 17 years in the travel and hospitality industry, she is driven by her passion for crafting unique and memorable journeys worldwide. Her expertise in curating bespoke travel packages across South Africa adds significant value to the Explore Sideways team.

Our Partners

We partner with leading brands in international travel