Discover your next cycling or skiing adventure with TwoSeasons
At TwoSeasons, we curate unique, high-class sports vacations tailored to the rhythm of the mountains. From spontaneous weekend escapes to once-in-a-lifetime expeditions, we craft the seamless details that turn every mile into a story worth telling.
Who we are and what we do
The Cyclist
We believe the luxury of a cycling adventure lies in the details: a perfectly tuned machine, a sun-drenched mountain valley and a private chef waiting at the end of a legendary ride. We handle the logistics of the road so you can lose yourself in the landscape. Whether you are chasing the beauty of the sea or the peaks of the Alps, we provide the ultimate sanctuary.
The Skier
For the passionate freerider and cross-country skier, the true luxury of the mountains is found in silence and fresh tracks. We specialize in deep-powder expeditions and pristine nordic skiing that connect alpine terrain with extraordinary nature. Our snow experiences are designed for those who seek the path less traveled, paired with the warmth of a world-class home.
The Team
Swiss entrepreneur and former athlete, Kevin Oberholzer has spent his life riding the world’s most iconic terrains. After exiting successful ventures, he returned to his deepest calling: the sea and mountains. Today, he brings his entrepreneurial precision to TwoSeasons and curates sports adventures around the world, that go far beyond a standard itinerary.
At TwoSeasons, our team hand-selects only the most iconic, minimalist retreats and spaces where clean lines and raw materials allow the landscape to take center stage. We believe that by stripping away the unnecessary, we create a sanctuary where you can truly reconnect with nature and the elements in their purest form.
Tailor-Made Adventures
By registering your non-binding interest, you're joining a pool of like-minded athletes and adventurers. Once we have a core group together, we’ll share full trip details and officially bring the journey to life.
Cycling in Sardinia, Italy
Dates & Duration: 7 days in October 2026
For the dedicated cyclist, our inaugural TwoSeasons Adventure takes you to the rugged coastlines and sun-scorched peaks of Sardinia - one of the Mediterranean's most untamed cycling destinations. Strictly limited to 8 riders, this experience is designed to pair the island's legendary maritime switchbacks and high-altitude climbs with a private sanctuary and a curated programme.
Special Experience - Strade Bianche
Dates & Duration: 5. – 8. March 2027 (4 days/3 nights)
For the dedicated cyclist, this Special Experience brings you to the heart of one of cycling's most iconic races – the legendary Strade Bianche. Strictly limited to a small group of riders, this experience is designed to combine the raw beauty of Tuscany's white gravel roads with premium comfort and a curated programme across four unforgettable days. Limited to 4 riders.
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