Portugal Moto | Leadership Series


October 8-14, 2023


The Wilderness – Leadership Series is a new offering where we host a world-class leadership coaching experience in the context of a bucket-list adventure. We want you to walk away with temporary bruises, lifelong friends and actionable wisdom to transform your business and leadership.
*Commercial invoices are available upon request.

This experience will be hosted with two Wilderness crew members documenting this trip of a lifetime along with leadership coach Stephen James bringing daily content.

*The Leadership Series trips are limited to 8 attendees to ensure an intimate group dynamic.


“Leading with Heart” comes from the core conviction that how you lead yourself is how you lead everything.

You will walk away with:

  • an increased personal and professional clarity
  • a reconnection to your sense of purpose
  • recovery from decision fatigue
  • knowing how to become burnout-proof
  • inspiration to be the best version of yourself at home and work
About Your Host: Stephen James

Stephen James is the founder Leadership Lab which provides successful leaders the clarity, courage, and confidence to live more purposeful, impactful, and influential lives through local membership communities and organizational leadership consulting.

Based in Nashville, Stephen has spent his professional career helping leaders live lives of meaning and significance in a variety of context, including:

  • sought after leadership advisor, consultant, and organizational therapist
  • mental performance coach for championship winning head coaches, athletes, and teams from a variety of environments including MLB, MLS, NFL, NHL, Olympics, USL, and the SEC
  • founder of Sage Hill Counseling and a private practice psychotherapist working with individuals, couples, and families.
  • co-author of seven books, including the bestselling “Wild Things: The Art of Nurturing Boys.”

Stephen earned his master’s in Counseling from The Seattle School of Theology and Psychology and his bachelor’s from Belmont University. He has been married to Heather for over 25 years, and together they have four adult children.


We’ve partnered with Horizon Adventures, the premiere enduro moto outfitters in Portugal. Their spirit of adventure and passion for hospitality matches the Wilderness Way.

The friendly Portuguese locals call this ride the “Atlantic Odyssey”. Five days of fantastic and epic riding as you explore the breathtaking country of Portugal. The beauty of “Costa Vicentina” is known as the last secret paradise on Europe’s West Coast and we’ll be experiencing it far off the tourist beaten path.

We’ll ride all kinds of terrain the country has to offer from fast winding roads, mountain trails, rocky sections, sandy sections and gorgeous take-it-all-in sections.

We’ll be staying in UNSECO world heritage towns, awarded rural hotels, country house style hotels and stopping at medieval villages. The food will be a highlight of the trip as we’ll be dining on the traditional Portuguese cuisine at unique restaurants and kitchens along the way.

Be sure to review the full itinerary to see all thats packed into this one experience.


• $7,500 per rider (All inclusive: KTM 450cc rental, leadership coaching, and $1k+ of add-ons)

• 30% deposit due upon booking. Balance due 60 days before departure
• Commercial invoices are available upon request.

Duration: 7 days, 6 nights, 5 riding days

Terrain: Primarily dirt and gravel forest service roads, rutted two-track dirt roads, short technical stretches involving rocks and loose sand, potential water crossings and pavement

Difficulty Level II: Intermediate riders with prior street and dirt experience will be well suited for this ride

Full Itinerary

Trip Includes/Excludes

  • Valid motorcycle license in your state/country
  • Previous off-road experience riding 100+ miles per day
  • Medical/Travel insurance with repatriation
Packing List

Digital Detox Policy

Leadership Series: Portugal Enduro Moto – 7 Day