Explore the Unexplored

From soil to glass, we believe that the world of wine elevates every experience. Our expert team have curated the very best specialist guides, private tours and luxury experiences for the discerning and curious traveller. Choose experiences from our collections or let us help design a tailor-made experience just for you.

Destinations We Specialise In

United States
Hungary
South Africa
Portugal

Experience a Wine Harvest in Portugal

Book an exclusive wine harvest experience in the iconic Douro Valley

Why Book with Us

Professional Specialist Guides

All of our guides are specialists in their respective fields with years of valuable experience and knowledge.  From historians and award-winning chefs to wine experts and art enthusiasts, we match-make you with the perfect guide.

Private Tours & Experiences

Each and every one of our tours and experiences includes a private vehicle and personal guide.  Get exclusive behind-the-scenes access to unique locations and activities without the stress of groups and crowds.

Every Detail is Sideways Approved

Our team of experts have approved every detail of our tours and experiences. With our guest’s wellbeing our top priority, extreme measures are implemented to ensure that everything from vehicles to venues follows strict health and safety guidelines.

Flexible & Personalised

Our luxury experiences and tours are completely flexible.  Designed to suit your personal preferences and travel needs, whether it’s a couple months before or the day of, we can adapt any experience to exactly what you’re looking for.

Experience Collections

Bucket List
Wine & Food
Adventure & Wellness
Art & Culture
Family-Friendly
Romantic Getaways

Read Our Latest Travel Stories

Explore Sideways Itineraries

Itineraries to Inspire You

Explore our latest collection of itineraries packed with luxury experiences to inspire your next vacation. These aren’t fixed itineraries, but rather a little something to whet the appetite. Everything that we do is designed just for you – ticking off every one of your travel quirks