Born in the UK I spent most of my childhood in East Africa returning to the UK in my mid-teens. At 18, I left the UK on an around the world ticket (my parents would say I actually never came back). Travel was certainly in my blood. I did get back to the UK eventually, five years later, but only stayed for a few months. Australia was home for a few years, and then New Zealand. A variety of jobs followed as a means of funding my love of travel. Eventually I joined the industry, spending 12 years in the corporate world working for a large travel organization based firstly in Australia, then South Africa, and finally New Zealand. New Zealand has been home base for the last 11 years and what an adventure playground it is.
​OTS adventures forward from Richard
​OTS has been a slowly evolving dream. Its structure has developed from many hours talking with people about their travel dreams, what they love, what they fear, and what they want to experience.  I have found with travel "less is often more" and the trips OTS run are more about getting to know a place, feeling and experiencing it, rather than ticking off lots of sights.
I am a person who loves the freedom of being solo, yet the travel industry is generally geared to couples. With OTS I hope to create the kind of holiday a solo person would love to be part of, as much as a couple would. Or, as often happens the adventurous half of a couple will join us, while partner is at home.
South America, Asia and Africa are great travel loves of mine, and I am always dreaming of new exciting destinations for  us to travel to.
Richard Clowes, founder, director, trip leader and tour creator.
The Future
My dream is for "Outside the Square"  to be the catalyst, bringing people together who love the kind of slow, experiential, mind expanding trips offered. People who know how to have fun, know that travel is often about the journey rather then the destination, expect the unexpected, and love to spend their money on experiences rather than things. 

OTS is a concept born of a passion to get "out there" and experience the world, without breaking the bank to do it. Our trips will always be about keeping costs low and value high, sourcing locally run accommodation and restaurants, and accessing Gay run or friendly businesses when we are able.
Life is richer when we have something to plan, save for, and look forward to, so join one of our trips and look ahead to many years of adventures, discovering new friends and new places.
Richard
Andrew Gunn, director, accounts and business guru. Tour leader and all around fun guy.
I’ve got to that certain stage in life, when I realize you need to focus on the important things in life, connect with awesome people and make magic travel moments with new friends that become lasting memories!
I know from experience how hard Richard strives to bring alive experiences on his tours.
Nine years ago, I was on a “Tango” trip to Argentina and Uruguay. I have vivid memories of that trip! The laughs, the meals, the drinks, the experiences together – that are so much more memorable than if I’d attempted to organize a trip myself.
I’ve worked with Richard before (it was another life!), and I’m truly excited to join Richard’s in his travel adventures. I’m looking forward to meeting the amazingly diverse travelers, listen and share our stories, and experience travel adventures that are truly outside of the square! See
you on tour – yours Andrew Gunn
Introducing our OTS family of Tour Leaders
All of our tour leaders, discovered OTS on previous adventures with us, and loving the concept, put their hands up to showcase the areas of the world they know and love best. Adventures for our community, by our community. 
​León (David) Esquenazi
Born in Brownsville, TX, on the US-Mexico border, my background is a rich tapestry of Spanish, Turkish, Greek, Cuban, and Bulgarian heritage.
Growing up bilingual and bicultural instilled in me an acute awareness and curiosity about diverse cultures and customs.
I believe travel is profoundly transformative, expanding our worldview, fostering empathy, and deepening our
connection to the world and its inhabitants.
Travel challenges assumptions, broadens perspectives, and cultivates empathy by encouraging engagement with diverse people and stepping out of comfort zones. It reveals shared humanity despite cultural differences and deepens connections, leading to lasting bonds and fostering a
sense of global citizenship. This transformative journey, which extends beyond mere sightseeing, is why I am passionate about sharing the world through curated experiences, especially within the OTS LGBTQ+ community, where shared journeys can uniquely affirm identity
and foster deep connection.
As I’ve discovered, Life is all about how we relate to the world and the people in it, and in the end, life is only rich in experiences; This resonates deeply with me, underscoring the importance of human connection and lived experiences over material possessions. Sharing
these rich experiences, particularly within a community that values connection and understanding, makes the journey even more resonant and fulfilling.

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​Walter Cloete
Proudly born and bred in South Africa. My journey started with a deep love for nature, which led me to study horticulture. During my student years, I traveled extensively across South Africa, developing a strong connection with the diverse landscapes and cultures of my home country.
After graduating, I served as Chief of Parks and Recreation for a local town council. But at 28, a trip to Europe changed everything—the travel bug bit hard. Ten months later, I resigned from my job and spent the next 18 months working and exploring overseas. That adventure sparked a lifelong passion for travel, freedom, and personal growth.
Back in South Africa, I founded my own landscaping company, which I ran for the next 33 years. Throughout that time, I made it a priority to travel as often as I could afford, eventually visiting 50 countries, most of them solo. I’ve always cherished my independence, but in 2019, I joined OTS on a trek to Everest Base Camp and later Cambodia and discovered how rewarding it is to travel with other like-minded adventurers.

Earlier this year, I had the opportunity to help Richard host the Cape Town Experience, and I absolutely loved it. Now, I’m looking forward to welcoming more OTS travelers, sharing the beauty of South Africa, and creating unforgettable memories together.
Howie Lee
If there's one thing that truly defines me, it's a passport full of stamps, a heart full of experiences, and a life surrounded by close friends.
I'm a bit of a global nomad by nature. My journey began in Malaysia, but my formative years were spent hopping across continents, from the vibrant landscapes of Sri Lanka to the bustling streets of Taiwan, before finally landing in the United States, where I currently call home. Growing up with such a diverse backdrop wasn't just a lifestyle; it became the very core of my identity.
For me, travel isn't just about visiting new places. It's about truly exploring the world; one culture, one cuisine, one custom, one sight, and one unforgettable smell at a time – and especially connecting with the incredible people who make each destination unique and unforgettable. I truly believe that every journey expands my worldview, enriching and enhancing my life in ways I never thought possible. My bones are practically aching for the open road, for new horizons, for the chance to meet fascinating new people, and most importantly, to feel truly alive again.
My first trip with Richard and OTS to Myanmar was nothing short of unforgettable! From the moment we landed, the energy was incredibly vibrant, exciting, and simply fascinating. Richard's travel style truly clicked with mine, offering that perfect blend of structure for the must-see sights while still giving me the freedom to explore other areas on my own and tailor the trip to my personal tastes. The pacing throughout the entire journey was absolutely perfect, never rushed but always engaging. I loved it so much that I went on 2 more trips with Richard!  And it's because of the unique style of travel that Richard and OTS offers that has inspired me to join the incredible OTS family. I can't wait to travel the world with new and old friends through OTS hosted adventures!