Many dream of the ultimate ski holiday with a supercar parked outside a lavish chalet, to heliskiing by day and a haute cuisine dining experience prepared by Michelin starred chefs at night. That is just one example of the many uber-luxe holidays provided by Leo Trippi. Ski Luxe Magazine sat down for a chat with CEO Oliver Corkhill to get his insights on ski, sail and multi-million-euro properties; the name of the game for Leo Trippi.

Leo Trippi’s most lavish properties fetch a million euros for a week in a chalet with a bowling alley, swimming pools and a cinema. Some estates have nightclubs for 100 people in private houses spanning 5,000 square metres plus. But no matter whether you’re spending 3,000 euros or a million euros with Leo Trippi, the personal touch is always present when it comes to accommodation, amenities, providing authentic local experiences and hospitality.

Founded by Florian Steiger, Oli Stastny and Auret van Zyl as an award-winning specialist travel company providing luxury chalets & tailor-made mountain trips around the world, the company was named after Florian’s great grandfather, Leo Trippi – a famous hotelier born in 1882. He ran three well-known hotels in Pontresina and Sicily. These were the ‘go-to’ places to stay for European socialites, business tycoons and royalty. Fast forward a century and the company is continuing the tradition as a leading authority in luxury ski chalets and mountain holidays. “At Leo Trippi, we approach business as we did in the authentic good old days of travel,” says Oliver. “That’s not to say we haven’t moved forward and modernised from that, but I think there’s a lot of nice touches from that bygone era.”

Oliver began skiing when he was living in Norway at age two and later went on a school ski trip aged seven. At the age of 11, he was hooked on skiing, and between dry slopes in the UK and two-month holidays in Switzerland, it was his main hobby. Once he turned 16, Oliver says, “I just had to be in the mountains, so I spent six winters in Verbier as a ski instructor. And then, it hit that I needed a longer-term career that connected skiing with business, so I started Alpine Guru in 2011, and grew that business to specialise in high-end chalet rentals for 300 clients. Leo Trippi approached the company and asked to buy them out.”

Having skied around the world, Oliver rates various resorts, for different reasons. For exhilarating trips with great freeride skiing and après, Verbier, Zermatt or St Moritz are his go-tos. That said, Bariloche in Argentina, Aspen and Deer Valley in the States also have their charms. For a quieter holiday, he prefers the Dolomites, Colfosco in Alta Badia Italy being his favourite resort. In his younger years, he loved Pub Mont Fort and Farinet in Verbier, but as he has grown older, places with live bands and dancing are ‘not his scene.’ Nowadays, he prefers a tranquil ski down the mountain to a wine bar: 1936 in Verbier is a new favourite. But wherever he is, the main thing for Oliver is being in a place with family and friends. He recalls “one New Year’s Eve, I decided not to go out but to hike up the mountain at 4.30 am to get the first track with two friends. We arrived at 8 am to enjoy fresh snow on New Year’s Day, which is an amazing memory that sticks in my mind.”

“Awesome service starts with guiding people to book the right holiday”, says Oliver. “People come across our website by referrals and we get a lot of business via word of mouth. It’s all about creating ‘wow’ moments. We aim to surprise and delight all our customers”.  Some of those ‘wow’ moments and exclusive travel opportunities include the ski and sail programme, their Michelin star dining, heliskiing which according to Oliver, are ‘absolute treasure trips, once-in-a-lifetime experiences.’

There is also the supercar tour in the mountains with a chalet skiing trip or a Michelin star dining experience, pairing some of the most well-known chefs in the world to a private chalet setting. Both tick the box in terms of where those luxury and lifestyles intersect. A simpler example of how this company makes holidays special is getting a ski guide to take a customer down a certain track with an amazing view and open a bottle of wine: “We are always trying to weave in magic touches along the way. That is the Leo Trippi way.”

Oliver has planned a lot of trips in his time, but his favourite was to Iceland for 20 people that involved a bonfire party on top of a volcano that took a snowcat to reach it. The trip also involved whale watching and skiing.

For the 2021 to 2022 season, heliskiing will be the next big thing, according to Oliver who says that many heli-lodges in places like Switzerland and Canada are fully booked for this winter. “This is fuelled by a huge pent-up demand to go skiing. People just want to get back to the mountains with family and friends and have a normal trip. It’s getting back to the basics of travelling and learning to enjoy skiing again.”

The company has relaunched the US as a ski destination to its UK customers due to increased demand. Since this route reopened Oliver expects more skiers will travel across the Atlantic. The most popular destinations are Aspen and Vail, although he rates Deer Valley and Park City in Utah. He also notes the rise in popularity of places like Steamboat Springs, accessible from Denver, for the real alpinist active skier. However, more intermediate skiers are guided towards the European resorts of the Three Valleys in France, namely Courchevel and Meribel.

Oliver also notes some amazing resorts in Japan are popular with the expat communities in Hong Kong and Singapore and some Australian clients. “We started taking them to Niseko – that’s a growing part of our business,” he said.  Other unique gems include Pamporovo, a popular ski resort in Smolyan Province in Bulgaria. “We have a beautiful house called Villa Gella combined with a city tour of Sofia.”

Approximately 40 per cent of Leo Trippi’s customers come from Russia and they tend to ask for European resorts. Of those Courchevel 1850 and St Moritz are popular. The firm favourites are Verbier, Zermatt, Val d’Isere, Meribel. Leo Trippi also has a great portfolio in Alta Badia in Italy and they launched a range of new properties in the Arctic which are growing in popularity given the natural socio-social distancing elements it offers.

Now, the ultimate question: luxury chalet or hotel? Leo Trippi’s clients book both, but most gravitate towards chalets. Ultimately, it comes down to space reveals Oliver. “I once preferred to be in a hotel, but I’ve slowly leaned towards booking private homes when I travel. Couples tend to opt for a hotel for a long weekend in a hotel, but groups of friends choose chalets.”

Oliver notes that trends have changed when it comes to customer preferences on dining. “Around a decade ago people wanted catered chalet experiences with a five-course meal on six nights of the week. But the way the world has changed, people want more flexibility and privacy, but with the same service. We give people can go out and experience that great restaurant and in times of covid, we bring great chefs to the chalets. It’s good to have a balance between eating out and in.”

Nowadays, many companies utilised private jet charter companies to keep people moving. Their top-end clients were using them already. Combining first-class commercial and private jet usage is not new for clients of this calibre and now there is a noticeable increase in people using it for shorter journeys to Europe. However, they have yet to make that leap when it comes to transatlantic. In the resort, there was already a trend moving towards more flexible service. “I don’t think we’ll have normal ski seasons again,” says Oliver. Looking ahead Leo Trippi will continue to plan great ski holidays and grow their business beyond Russia and the UK and open a new office in the Middle East.”

Meeting the man behind Leo Trippi and getting a unique insight into how his progressive company has  been an enlightening experience. With such a long heritage and exciting vision for the future, this dynamic company will surely continue to develop world-class ski holidays for top-end and ultra-wealthy clients for many years to come. Already recognised as the ‘World’s Best Ski Travel Agent’, with Oliver Corkhill as the CEO, the company will continue to scale new heights of luxury.