Leadership Cycling Tour

Challenge for your body.

Adventure for your soul.

Inspiration for your mind.

Experience a leadership retreat on two wheels.

Cycle the scenic back roads of Lake Michigan with a small cohort of driven leaders. This exclusive cycling tour blends endurance and high-level business collaboration in a guided multi-day leadership experience.

Riders will travel along the stunning west coast of Michigan, following quiet back roads and dedicated bike paths through some of the region’s most charming lake towns. Expect rolling hills, sweeping lake views, historic lighthouses, sandy dunes, and welcoming small-town hospitality. Some routes will involve state highways.

This is a self-supported cycling experience with each rider carrying their own gear. Daily distances range from 50–75 miles (optional 2 day Northern Michigan Extension allows longer mileage). Pre-tour training is required, and check-ins will be scheduled for accountability and support.

Leadership Cohort & Collaboration

This tour is designed as a cohort-based leadership retreat. During the day, we are riding, conversing, building relationships, and discussing leadership. Each evening, the group gathers over dinner where each participant will present a current business, leadership, or organizational challenge. The group will offer questions, perspectives, and strategic insight to create a collaborative environment where experienced leaders help one another solve real problems.

“If you work with your mind, rest with your hands. If you work with your hands, rest with your mind.”

- attributed to Abraham Joshua Heschel

Tour Highlights

  • Ride through picturesque Lake Michigan towns including:
    Michigan City, New Buffalo, St. Joseph, South Haven, Saugatuck, Holland, Grand Haven, Ludington, Pentwater, Frankfort, and Traverse City.

  • Experience quiet back roads, scenic shoreline routes, and dedicated bike paths, along with some urban riding on state highways.

  • Take in the beauty of sweeping Lake Michigan vistas.

  • Enjoy single-occupancy lodging each night in comfortable hotels, motels, or Airbnb’s.

  • All breakfasts, lunches, and dinners included.

  • Create memories and build networking relationships with a small group of high-capacity peers.

Sample Route & Daily Mileage

Day 1: Crown Point, IN → New Buffalo, MI: +/- 55 miles

Day 2: New Buffalo → South Haven: +/- 55 miles

Day 3: South Haven → Muskegon: +/- 70 miles

Day 4: Muskegon → Ludington: +/- 65 miles

Optional 2 Day Northern Michigan Extension:

Day 5: Ludington → Frankfort: +/- 70 miles

Day 6: Frankfort → Traverse City: +/- 85 miles

Frequently Asked Questions

  • $3150 per participant (Crown Point - Ludington)

    • Includes 3 nights lodging (single occupancy in New Buffalo, South Haven, Muskegon)

    • 3 breakfasts, 4 lunches, 4 dinners

    • Guided touring & Leadership facilitation

    • Pre-trip check-ins

    If desired, the 2 Day Northern Michigan Extension (Ludington - Traverse City) can be added for $1550 per participant.

    • Includes 2 additional nights lodging (Ludington, Frankfort)

    • 2 breakfasts, 2 lunches, 2 dinners.

    A $1,000 non-refundable deposit is required to reserve your spot. Remaining balance is due 30 days prior to departure.

  • Sept. 9-12, 2026 (Days 1-4: Crown Point, IN - Ludington, MI)

    Sept. 13-14, 2026 (Days 5-6: Northern Michigan Extension: Ludington - Traverse City)

  • To build camaraderie and ensure readiness, participants will take part in three pre-trip virtual sessions focused on:

    • Training accountability and physical preparation

    • Gear planning and packing guidance

    • Tour logistics and safety

    • Early relationship building within the cohort

    • Answering questions

    • Optional training rides available for those in the northwest Indiana region.

    • 4 days / 3 nights guided cohort experience (optional 2 day extension additional)

    • Single-occupancy hotel, motel, or Airbnb lodging

    • Breakfast, lunch, and dinner each day

    • Pre-trip planning and training calls

    • Leadership facilitation and collaborative discussion sessions

    • Personal cycling equipment, bike, helmet, and gear

    • Snacks while riding

    • Alcoholic beverages

    • Souvenirs or personal purchases

    • Transportation to the start of the trip (Crown Point, IN) and from the final destination (Ludington, MI or Traverse City, MI). Each rider must arrange their own drop-off and pick-up.

  • This experience is designed for:

    • C-suite leaders, entrepreneurs, founders, business owners

    • Senior leaders, pastors, and high-capacity leaders who oversee departments and/or teams

    • Participants must be physically active and healthy. Pre-trip training is required to participate.

  • We will be riding in a group along designated bike routes and secondary roads, utilizing helmets, wearing bright clothing and using flashing bike lights for visibility.

    However, there is inherent danger to riding on public roads. Participants must ride within their own limits and sign a liability waiver prior to departure. This is an endurance cycling event on public roads, and each rider assumes responsibility for their own safety, physical conditioning and health, and decision-making throughout the trip.

  • We are riding between 50-75 miles per day, with an average speed of 13-15 mph. We will take frequent stops for rest, coffee, and snacks. Our total time in the saddle every day will be between 4—6 hours.

    The West Coast of Michigan has many small towns along the route with cafes, restaurants, shops and convenience stores available with food, restrooms, water, and supplies.

  • Each cycling tour includes myself plus 2-5 participants.

  • Yes, with a minimum group size totaling 3 of us! Please reach out to discuss alternative dates and options.

Let’s ride!

Reserve your spot or reach out with questions.

Header Photo by Impresso Studios