Forty Years on Lake Michigan: A Day Aboard Capt. John Kummerer’s Chicago Charter

CHICAGO SAILING FIELD GUIDE

Forty Years on Lake Michigan: A Day Aboard Capt. John Kummerer’s Chicago Charter

A 3–4 hour Lake Michigan sailing from 31st Street Harbor with Capt. John Kummerer of Knot My Boat Charters — this guide explains what to expect and how to plan.

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Forty Years on Lake Michigan: A Day Aboard Capt. John Kummerer’s Chicago Charter.

Duration
3-4 Hours
Location
Chicago
Operator
Knot My Boat Charters
Category
Sailing
Robert Eric Crews
Founder & Editor, The Adventure Collective
Published Verified

On a clear day the city edge loosens and the scale changes: Chicago’s skyline gives way to the broad, bracing sweep of Lake Michigan. Capt. John Kummerer, a seasoned sailor whose enthusiasm for the water is as immediate as his laugh, runs private charters that range from relaxed cruises to event-driven outings. His decades at the helm shape those hours on the lake into something both safe and memorable.

Highlights

Outing Highlights

THE CAPTAIN

Decades of seamanship, a lively guide

Capt. John brings more than 40 years navigating Lake Michigan to every charter. His easy humor and deep experience are the foundation for comfortable, confident days on the water.

THE ROUTE

A compact, city‑edge cruise

Typical outings leave from 31st Street Harbor on J Dock for a 3–4 hour experience on Lake Michigan, designed to balance open-water sailing with time to relax and take in the city-from-the-water perspective.

THE OCCASION

Charters built for celebrations and groups

The service is offered for a wide range of gatherings—bachelor/bachelorette parties, corporate events and similar group bookings are explicitly mentioned—so the boat can serve as both a relaxed cruise and a setting for special occasions.

What the day feels like

What the day feels like

Expect three to four hours anchored in the rhythm of the lake: a brief boarding at the J Dock slip, a stretch of open-water sailing where the city recedes, and ample time to enjoy company, conversation, and the small rituals of a private charter. The captain’s decades of experience shape both the pace and safety of the outing.

Suitability

Who it's for

Who this charter suits — and where you should double‑check details with the operator.

1
Event groupsThe service explicitly calls out bachelor/bachelorette parties and corporate events as typical uses, making this a strong match for small-to-medium celebratory or professional gatherings.
2
Couples & small friend groupsA 3–4 hour cruise provides a tidy window for a relaxed outing or a short adventure on the lake — suitable for couples and small groups looking for an easy, private experience.
3
First‑time sailorsWith Capt. John’s decades of experience and an approachable style, first‑time passengers can expect confident guidance and a welcoming atmosphere.
4
Travelers with accessibility or health concernsThe listing does not provide specific age, participant‑limit, or health restriction details; anyone with mobility or medical considerations should contact the operator to confirm suitability.

Practical planner

Details to review before reserving

Duration

Typical charters run 3–4 hours.

Meeting point

Boarding is at 31st Street Harbor on J Dock.

Rates

Rates start at $100 per hour.

What to bring

No formal gear list is provided in the listing; guests should bring weather‑appropriate layers, sun protection, and any personal essentials, and contact the operator for specific recommendations.

Booking Notice

Review cancellation policies before reserving.

Frequently asked questions

Planning Your Outing

How long is a typical charter?

Charters are typically 3–4 hours in duration.

Where do we meet the captain?

Meeting and boarding take place at 31st Street Harbor on J Dock.

How much experience does Capt. John have?

Capt. John Kummerer has over 40 years of experience navigating Lake Michigan.

How much does a charter cost?

Rates start at $100 per hour.

How do I contact or book?

You can call or text Capt. John at 708‑738‑1166 to inquire about availability and to book.

What kinds of events are appropriate for this charter?

The listing specifically mentions bachelor/bachelorette parties and corporate events among the intended uses.