
Extraordinary adventures.
Designed for your second mountain.
WAYFINDERS Adventures take bold entrepreneurs like you to some of the most spectacular and wild places on the planet for ADVENTURE, community and personal transformation.
Each Adventure is a carefully curated experience in a spectacular place, designed to spark courage, deepen connection, and catalyze transformation.
Read more about our approach to human transformation and flourishing
PATAGONIA VIP
NOV. 30-DEC. 08, 2025
A yearlong ‘Second Mountain’ journey for entrepreneurs with $3M+ in annual company revenue, culminating in a spectacular Adventure in Chilean and Argentinian Patagonia.
Challenge Level: 4/5
Off-the-Map Factor: 2/5
ratings explained
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How physically demanding is this Adventure?
All Wayfinders Adventures are active, often more so than the average tour. Even our “lighter” experiences may include moderately long hikes or sustained activity. This scale will help you choose an experience that meets your current capacity - and stretches you just the right amount.1 – Active, but accessible
Expect up to 10–15 km of hiking per day on varied terrain. Suitable for anyone with basic fitness who enjoys long days outdoors.2 – Moderate challenge
Daily activity might include 15–20 km of hiking, moderate elevation gain, or sometimes sustained activity (6–8 hours). You’ll feel it, but it’s doable with preparation.3 – Strong challenge
More demanding terrain, higher elevations, or consecutive days of significant exertion. Good fitness and preparation are important.4 – Very demanding
Intense daily exertion, high altitude, or rugged conditions. Requires very good fitness and mental stamina.5 – Extreme challenge
Expedition-level demands, such as climbing a 20,000-foot volcano or multi-day treks at altitude. For fit, well-prepared adventurers only.
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How familiar or unfamiliar will this experience feel?
Some Adventures take place in settings that feel comfortable and familiar, even luxurious. Others bring you into deeply rustic, remote, or culturally different environments (sometimes there’s a mix of both). Each has its magic - this scale helps you understand what kind of "edge" you’ll be walking.Level Descriptions:
1 – Familiar & comfortable
Settings feel close to home for Western travelers. Think boutique lodges, reliable amenities, and creature comforts intact.2 – A touch of the wild
Still largely comfortable, but with occasional rustic or unusual moments: a remote lodge, an outdoor meal, or cultural immersion.3 – Rugged, but balanced
A mix of comfort and wilderness: perhaps tented camps, homestays, or limited amenities, combined with some familiar touchpoints.4 – Remote & rustic
Mostly unfamiliar environments: multi-day camping, minimal connectivity, unpredictable logistics. Comfort takes a back seat to immersion.5 – Deep wilderness / cultural edge
One of the most remote or unfamiliar experiences you’ll ever have: full immersion in wilderness or traditional ways of life, with little to no infrastructure, often rustic and raw. True adventure.
ARABIA
mar. 1-9, 2026 (4 spots left)
9 magical days in the vast and beautiful wilderness of NEOM, Saudi Arabia and Egypt’s southern Sinai peninsula, trekking with the Bedouins and culminating in an ascent of Egypt’s highest peak, Mt. St. Catherine.
A journey through silence and history, in an area rich with significance for all 3 of the world’s major religions.
Challenge level: 3/5
Off-the-Map Factor: 4/5
Unshakeable: ICELAND
may. 24-29, 2026 (8 spots left)
Unshakeable: Iceland is a collaboration with the legendary coach Philip McKernan, at a remote and private resort just 90 minutes from Keflavik airport.
In the wild terrain of Iceland, you’ll reconnect to your internal compass, uncover your next mission, and build the inner resilience to pursue it.
Challenge level: 2/5
Off-the-Map Factor: 2/5
bhutan
oct. 8-17, 2026 (3 spots left)
On our 3rd visit to the remote Buddhist kingdom of Bhutan, we’re heading into the heart of the Himalayas and some of Bhutan’s most remote communities, while spending time with our favourite monks and trekking to the world-renowned Tiger’s Nest monastery.
Challenge level: 3/5
Off-the-Map Factor: 4/5