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.
Country Manager - Portugal
Hailing from the vibrant city of Porto, Filipe now lives in the Douro Valley amongst the vines working hard in his spare time in creating his own wine label. With a background in communication and public relations, he has worked in wine tourism at some of Portugal’s top port wine brands - Taylor’s, Croft and Fronseca.
Guest Experience Manager - Portugal
Marcel is our Guest Experience Manager designing the perfect experiences in Portugal and Spain. As an avid globe-trotter having visited more than 50 countries across the world and years of experience the the travel industry, he understands the needs of travellers and how to make their travel experiences ones that they’ll never forget.
Product & Business Development - Portugal
Hannah is a worldwide entrepreneur with a strong background in international hospitality management. After living in Switzerland, China, and Brazil where she launched a boutique hotel, she is now back in Europe. Specialised in developing, creating and implementing foreign companies in Portugal, she is now responsible for launching Explore Sideways Portugal.

Our Partners

We partner with leading brands in international travel