CHICAGO BOAT TOUR FIELD GUIDE
Glide the Chicago Skyline with Captain Arlo Kallemeyn
A 3–4 hour luxury powerboat outing on Lake Michigan where Captain Arlo guides guests past Chicago’s skyline and shares his life on the water.
Glide the Chicago Skyline with Captain Arlo Kallemeyn.
Glide past Chicago’s skyline aboard a luxury powerboat and feel the wind off Lake Michigan as Captain Arlo Kallemeyn—an experienced sailor, kayaker and angler—introduces the city from the water. The outing emphasizes the immediacy of the lake and the skyline, framed by a captain who has lived most of his life near these waters and makes showcasing the city his specialty.
Highlights
Outing Highlights
Chicago’s architecture from the water
The core of the experience is a scenic cruise on Lake Michigan that places the city’s skyline in view from angles only the water provides—an uninterrupted, low‑angle perspective best experienced from a powerboat.
A guide steeped in life on the lake
Captain Arlo has lived most of his life near Lake Michigan; his personal history—racing sailboats, kayaking rivers and salmon fishing—shapes the way he introduces clients to Chicago by water.
Luxury powerboat platform
The outing is delivered from a luxury powerboat, the platform Captain Arlo specializes in for presenting the skyline and the lake.
What the day feels like
What the outing feels like
Across a 3–4 hour window you’ll depart from a harbor slip and run onto Lake Michigan to take in Chicago’s skyline while the captain narrates and shares his enthusiasm for boating life—sailing, kayaking and fishing inform his perspective—creating a relaxed, memory‑driven cruise.
Suitability
Who it's for
Who this outing suits—and where to check before you book.
Practical planner
Details to review before reserving
The outing is a summer‑friendly way to enjoy Chicago by water; the advertised duration is 3–4 hours.
No operator‑specified gear list is provided in the available details; verify required items (sun protection, layers, motion‑sickness remedies, camera) with the operator.
Boarding is at 31st Street Harbor on J Dock; confirm arrival time and any additional logistics with Knot My Boat Charters.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
Where do we meet for the trip?
The meeting and boarding point is 31st Street Harbor on J Dock.
How long is the outing?
The advertised duration of the outing is 3–4 hours.
What will we see on the cruise?
The cruise glides past Chicago’s skyline from Lake Michigan aboard a luxury powerboat while the captain shares his perspective on boating and the city.
Who operates this experience?
The trip is run under Captain Arlo Kallemeyn and operated by Knot My Boat Charters.
What should I bring with me?
The available information does not include an operator‑specified gear list; contact the operator to confirm recommended items.
Are there age or health restrictions?
No specific age or health restrictions were provided in the available details; confirm any limits with the operator before booking.