About Two Brothers Sailing Adventures
Private charters from Montrose Harbor—built for skyline sails, summer weekends on the lake, and guests who want a captained Chicago boating experience without the crowd.
Our Story
Two Brothers Sailing started on the water, with family. What began as shared weekends on Lake Michigan turned into a promise: host every outing like friends are aboard—safe, warm, unforgettable skyline light.
Today we pair a curated fleet with captains who know Montrose Harbor, the Playpen, and the best angles for sunset and fireworks—private, premium, unmistakably Chicago. Explore private Chicago sailing charters, meet the Vagabond sailing yacht, or browse events and special occasions.
Private charters & lessons
Curated fleet for small groups—sunset, fireworks, Playpen, and hands-on sailing.
Packages shaped around your pace, not a one-size template.
Lake Michigan routes
Skyline sails, harbor hops, and Playpen days with captains who know the chop.
We route for breeze, views, and comfort—never a generic loop.
Captain-led, end to end
USCG-licensed skippers on every outing—briefing, lines, and safety covered.
The same hospitality mindset from inquiry to dock-out.
Meet your crew
Directions & Parking
333 W Montrose Harbor Dr, Chicago, IL 60640, United States
Public parking and harbor access off Montrose and Lake Shore Drive; your captain texts the slip and meeting point the day before. Allow extra time on summer weekends and event nights.
Arrival: 30 minutes early
Get directionsChicago sailing charters · neighborhood guide
Private Lake Michigan yacht charters depart from Montrose Harbor—no matter which Chicago neighborhood you call home, here's how long the drive typically takes (light traffic), plus a shortcut to a tailored landing page for each of the city's 77 official community areas. Tap a card to explore captained sunset sails, skyline routes, Playpen days, and fireworks nights built for your crew.
Estimates only—summer weekends, Navy Pier fireworks, and the Air & Water Show can add serious time on Lake Shore Drive. Build in buffer, arrive 30 minutes before departure, and we'll handle the harbor details by text.
2026 Summer Calendar
Navy Pier shows, July 4th week, and festival weekends—hold dates early for best slips.
Captain-planned sightlines away from shore crowds; limited tickets on select vessels.
Raft-up energy when the lake is warm—afternoon blocks with swim ladders and sound zones.
Request our events kit or ask us to pencil a window while you coordinate guests—we confirm weather buffers and captain availability before you lock a deposit.
Sponsorships
We work with a small number of brands and nonprofits that align with safe, inclusive boating on Lake Michigan—education, stewardship, and memorable on-deck moments instead of logo clutter.
Interested in co-branded sails, youth access, or harbor clean-up days? Reach out through booking and we'll share 2026 opportunities.
Jeff
Captain
Jeff is a USCG-licensed captain with over 15 years of experience on the water. He has captained everything from 60-foot motor yachts and sailboats to 14-foot dinghies, bringing a deep mix of skill, confidence, and practical know-how to every charter. Guests love Jeff's easygoing energy, fun personality, and laid-back style behind the helm.
Billy
Captain
Billy is a USCG-licensed captain with over 5 years of experience and a straightforward, down-to-earth approach that guests appreciate. With a background in city planning and construction, he brings a unique perspective to Chicago's skyline, lakefront, and architecture. Ask him a question, and you'll probably get a great story with your answer.
Cedrick
First Mate
Cedrick is the first mate and captain-in-training, working toward taking the helm himself soon. Until then, he helps make sure every guest has a smooth, comfortable, and memorable experience aboard. Whether he's assisting the captain, helping guests settle in, or keeping the trip running smoothly, Cedrick is there to make the day on the water feel easy and enjoyable.
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