Oliver Corkhill

Spear’s Review

Oliver Corkhill is the co-founder of the Viadi Group, a collection of high-end travel companies, but it is for Leo Trippi, the award-winning ski operator, that he is recommended by Spear’s.

Winner of world’s best ski travel agent at the World Ski Awards for 11 consecutive years, Leo Trippi specialises in the most exclusive ski chalets and hotels in resorts in Europe, and its heli-skiing tours have been featured in publications such as Elite Traveller.

Corkhill tells Spear’s that Leo Trippi works with ‘a globally diverse pool of HNW and UHNW clients’ to create tailor-made adventures. As well as sourcing luxury ski chalets with a range of spa facilities, Corkhill’s firm is also adept at helping World Economic Forum delegates to find accommodation each January in Davos and to access Mediterranean villas in the summer months. According to the agency, it offers a ‘curated collection’ of 400 properties across 33 resorts.

Adviser Profile 

When it comes to advice on where you should go skiing or which luxury chalet you should rent, you need to speak to Oli Corkhill. His agency, Leo Trippi, is regarded as best in class and specialises in the best ski chalets around the world – with exceptional service to match – whilst also offering more adventurous experiences such as heli-skiing in Patagonia or adventuring to the polar regions. 

Oli is often travelling the world to scout new places to stay and experiences for his little black book of clients who come from all over the world. Oli started out as a ski instructor in Verbier when he was 16 and spent the best part of six years following the snow around the world before settling in the Cotswolds. At 21 he founded chalet specialist Alpine Guru, which merged with Leo Trippi in 2016. A little over a year later Oli had become CEO, and fast-forward to today the company has been named as ‘World’s Best Ski Travel Agent’ for 11 consecutive years. 

In 2022 Oli co-founded Viadi Group and acquired a highly bespoke tour operator, Explorations Company, which was by chance based 10 minutes from his house. They then bought WhereToStay.com, which is a leading Caribbean villa rental agency based out of Texas, before adding global villa specialist Edge Retreats to the mix just a few months later. The companies have offices in Switzerland, the UK, the UAE and the United States, serving a globally diverse client base.