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.
Chief Experience Officer
Michelle is our CEO and goes to every length to ensure that the Explore Sideways team deliver the best possible experiences for our Guests. After years in Brazil, Michelle moved to Cape Town, fell in love with the Mother City and the rest, as they say, is history.
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.
Guest Experience Manager - Portugal
Marcel is our Guest Experience Manager based in Portugal, he designs perfect experiences for our Guests in both Portugal and Spain. As an avid globe-trotter and years of experience in the travel industry, Marcel understands the needs of travellers and how to make their travel experiences ones that they’ll never forget.

Our Partners

We partner with leading brands in international travel