The good Saturdays sail off the calendar first.

Fireworks nights, golden-hour sunsets, and peak summer weekends all compete for the same handful of slips—ping us with your dates and we'll help you lock a boat and route before someone else grabs the breeze.

Lock in your sail

No pressure pitch—just dates, headcount, and what you're celebrating.

Two Brothers Sailing Adventures

Montrose Harbor — Dock G
333 W Montrose Harbor Dr, Chicago, IL 60640, United States

Email: TBD

(630) 816-1427

Chicago sailing experiences

Private Lake Michigan cruises
Chicago Playpen sailboat charters
Skyline sunset sailing
Navy Pier fireworks cruises
Chicago sailing lessons
Proposal & engagement charters
Celebration & party sails

Charters

All charters
Chicago Sunset Sailing Charter
Chicago Fireworks Sailing Cruise
Chicago Playpen Sailboat Charter
Chicago Lake Michigan Cruising Charter
Chicago Sailing Lessons
Lake Michigan Scuba Trips

Fleet

Meet the fleet
Vagabond
Drifter
Blue Moon

Events

All events
Chicago Air and Water Show Boat Charter
Fourth of July Boat Charter Chicago
Memorial Day Weekend Boat Charter Chicago
Labor Day Weekend Boat Charter Chicago
Chicago Summer Boat Charter
Birthday Boat Charter Chicago
Bachelorette Boat Charter Chicago
Bachelor Boat Charter Chicago
Date Night Boat Charter Chicago
Proposal Boat Charter Chicago
Anniversary Boat Charter Chicago
Corporate Boat Charter Chicago
Family Boat Charter Chicago

About

About us
Our story
Meet your crew
Policies & weather
Directions & parking
Montrose drive times
2026 summer calendar
Sponsorships

Contact us

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