Toby Winn
Travel Advisor & Co-Founder
Based in East Worldham, near Alton, Hampshire. Over a decade in the travel industry and first-hand experience across 55+ countries.
Toby Winn
Co-Founder
Looking for advice on your next trip?
Whether it’s a simple beach break or something more complex, I’m always happy to talk through ideas and help shape the right itinerary.
Planning travel has been part of my life for as long as I can remember. What started as a degree in Travel & Tourism became over a decade working across the industry in the UK and overseas.
I’ve visited more than 55 countries and lived in Hong Kong, Malaysia and Thailand. I’ve worked for long-haul specialist Travelbag, managed ground product reservations in the UK, worked for a tour operator in Bangkok handling client relations and tours, and spent time working in hotels in Langkawi and Phuket.
That combination of retail, ground operations and on-the-ground hotel experience gives me a practical understanding of how trips actually run, not just how they’re sold.
Travel Experience
Having travelled to more than 55 countries, I draw on a wide range of first-hand experience when planning trips.
Asia remains a particular strength. Thailand, Malaysia and Bali are places I know especially well, not just from short visits but from living and working there.
I also have strong experience planning itineraries across Australia, South Africa and the USA, as well as trips throughout Europe and the Caribbean.
A few personal highlights include exploring the Bungle Bungles in Australia, visiting Angkor Wat in Cambodia, travelling overland from Hanoi to Ho Chi Minh City and relaxing in Zanzibar.
What I Enjoy Planning
I genuinely enjoy planning all types of trips. Every holiday matters to the person taking it, whether it’s a long weekend or a once-in-a-lifetime journey.
That said, I particularly enjoy:
Long-haul itineraries
Multi-centre trips
Asia and Australia
Safari and beach combinations
Complex trips that need careful structuring
I tend to look at the bigger picture first, then refine the detail so everything runs smoothly.
How I Work
I would describe my planning style as organised, thorough and willing to look at alternatives rather than defaulting to what everyone else offers.
I believe travel advice should add value.
Many people assume booking everything themselves is cheaper or better. Sometimes it works. Often it’s time-consuming, fragmented and lacks proper protection.
My role is to compare options properly, explain what represents genuine value and structure the trip so it feels effortless from the start.
I focus on building long-term client relationships rather than one-off bookings.
Life Outside Travel
I’m based in East Worldham, just outside Alton in Hampshire, with my wife and three children. Travel is very much a family passion for us.
When I’m not planning trips you’ll usually find me playing padel or training at CrossFit.
I also speak Malay and basic Thai, which has been useful more than once.
Travel Philosophy
A great trip doesn’t happen by accident.
It comes from understanding the destination, structuring it well and thinking ahead. My aim is always the same: to make sure your holiday feels considered, well paced and worth every penny.