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Simon Maddison

Executive Chairman

Simon has always enjoyed travelling to remote and challenging destinations and the personal challenges that overland travel presents. He believes that Sundowners Overland is an ideal company to encounter these travel experiences with. Simon joined Sundowners Overland following 10 years of leading a nomadic lifestyle that included hitch hiking across Africa, working in Nigeria, crewing on a boat in the Mediterranean, picking grapes, gathering walnuts and managing a campsite in France before joining Encounter Overland as an expedition Leader/Driver in Africa and Asia. It suits Simon’s adventurous nature to be involved in creating and bringing to life unique and adventurous journeys that allow travellers to step beyond their travel ‘comfort zone’ to experience new and exciting destinations.

What do you love most about overland travel?
The excitement and anticipation of crossing the next border to experience a completely new people, language, culture and food.

 Which of the Sundowners Overland destinations fascinates you most?
Western Mongolia, The Caucasus and Tadjikistan – as they will be new destinations and experiences for me (and everyone I have met who have visited these regions has returned with great travellers’ tales).

 Give us your best tip for travelling on Sundowners Overland journeys.
Travel with an open mind and allow yourself to enjoy the many new experiences  each day.

 What is your most memorable travel experience?
The most memorable experiences have always been those unplanned and unexpected encounters  that seem to occur with greater frequency the more remote and challenging the journey is.

 Which Sundowners Overland journeys are on your wish list?
Any journey to Mongolia, Iran and the Caucasus

 What is your favourite season to travel?
I prefer to avoid the crowds and extreme seasons, so destinations away from the main tourist areas or out of high summer or mid-winter (although my favourite season on the Trans Siberian is winter!)

 Where have you travelled in the world?  

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Trans Siberian Express - Twin Gold Class-15 days

Undoubtedly the world's greatest railway journey, the Trans-Siberian Railway runs like a steel ribbon connecting east and west from Moscow over the Urals, across the magnificent more...