Meet the team

Matthew O’Sullivan

Since an early age, travel has always been in my blood and when not devouring Geography at school, I would head off on my bike for hours exploring the country lanes around my hometown Harrogate in North Yorkshire .

After graduating in London having studied, you guessed it, Geography! I worked for a tour operator specialising in countries that were a challenge to visit back in the early 1990s, including the Soviet Union, China, Albania and more. This led me onto boarding the first ever flight from the UK direct to Havana and as they say the rest is history and the love affair began…

As a young man in his 20s Cuba was just amazing, hot sunny days, beautiful scenery, amazing beaches, such welcoming locals sharing the same sense of humour as us Brits, music, dancing , great food, illicit cigars and most of all a feeling that you were somewhere totally different to home.

A career almost totally dedicated to Cuba beckoned and over 35 years I have enthusiastically arranged and managed countless thousands of tailored holidays for clients. This has included arranging the one and only Concorde arrival to Havana with a group of over 120 clients, met on arrival by Fidel Castro. There has been numerous celebrities and film crews, including accompanying a couple from the hit TV series Blind Date who loved Cuba but hated each other !

I have travelled throughout Cuba many times, including a lot of cycling, walking and ticking off Pico Turquino, Cuba’s highest peak. I am therefore delighted to be able to give you firsthand knowledge of Cuba , warts and all.

I love to chat and very honestly answer all those Cuba questions that you may have, even if just general questions about the island . My experience has shown that Cuba is always in people’s minds as a destination they would love to visit one day , so let’s maybe arrange a call for an initial chat