Two Brothers Sailing Adventures

About Two Brothers Sailing Adventures

A Chicago sailing crew,rooted on Lake Michigan

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

from weekend sails to a Chicago charter fleet

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

the people behind the helm

Jeff and Billy are USCG-licensed captains; Cedrick serves as first mate and captain-in-training—the tight-knit team you meet at Montrose Harbor. Same briefing style every charter: safety-forward, hospitality-heavy, and calm under sail.

Policies & Info

full weather & cancellation policy

Your safety, clear expectations, and what happens if plans change—deposits, weather, routes, and cancellations in plain language.

Weather policy

Your safety comes first. Two Brothers Sailing Adventures monitors Lake Michigan weather, marine forecasts, wind, waves, storms, visibility, lake traffic, and other conditions before every charter.

Lake Michigan conditions can change quickly, and the weather on the water may feel different than it does on land. Because of this, Two Brothers Sailing Adventures reserves the right to determine whether a charter can safely operate.

Charters may still operate in light rain, cloudy weather, cooler temperatures, or moderate breeze when conditions are safe. A cloudy day, cooler temperature, or light passing rain does not automatically make a charter unsafe or eligible for cancellation.

Conditions that may be considered unsafe include, but are not limited to:

  • Severe thunderstorms
  • Lightning
  • Small Craft Advisories
  • Gale warnings
  • Unsafe wind or wave conditions
  • Dense fog or poor visibility
  • Other unsafe boating conditions at the captain's discretion

If lake or weather conditions are deemed unsafe, we will work with you to reschedule your charter for another available date. Weather-related rescheduling credits do not expire and may be applied toward a future charter of equal or lesser value.


Route, timing, and experience adjustments

Routes, timing, anchoring, swimming, sunset views, fireworks visibility, Playpen access, and special event viewing may vary based on weather, lake conditions, lake traffic, safety zones, event operations, and captain discretion.

If conditions are safe for boating but not ideal for a specific route or activity, the charter may still operate with an adjusted route or alternative Lake Michigan sailing plan.


Sunset charters

Sunset visibility is not guaranteed. Cloud cover, haze, rain, or changing weather may affect sunset views, but the charter may still operate if lake conditions are safe.

If conditions are unsafe for boating, we will help reschedule your charter according to our weather policy.


Fireworks cruises

Fireworks are controlled by outside event organizers, not Two Brothers Sailing Adventures. Fireworks may be delayed, canceled, shortened, or affected by weather, visibility, lake traffic, or event operations.

If the charter itself can safely operate, the charter may proceed even if fireworks are delayed or canceled by the event organizer. If lake or weather conditions are unsafe for boating, we will help reschedule according to our weather policy.


Playpen charters

Playpen access, anchoring, swimming, and route timing depend on weather, lake conditions, traffic, safety zones, and captain discretion.

If conditions are safe for sailing but not ideal for the Playpen, the charter may operate with an adjusted route or alternative Lake Michigan sailing plan.

Swimming is never guaranteed and is only allowed when conditions, location, and captain discretion permit.


Special event charters

Special event charters, including the Chicago Air and Water Show, Fourth of July, Memorial Day Weekend, Labor Day Weekend, and other high-demand dates, may be affected by lake traffic, safety zones, event operations, weather, and visibility.

Two Brothers Sailing Adventures does not control public event schedules, fireworks, Air and Water Show flight paths, safety zones, or event changes. A charter during a special event provides a private Lake Michigan experience during the event window, but exact show visibility, route, timing, or viewing location is not guaranteed.


Cancellation policy

Cancellation requests must be submitted in writing by email.

30+ days before charterDeposit is non-refundable.
15–29 days before charter50% of the total charter price is non-refundable.
14 days or fewer before charter100% of the total charter price is non-refundable.

Rescheduled charters remain subject to availability. Weather-related rescheduling credits do not expire and may be applied toward a future charter of equal or lesser value.


Guest responsibility

Guests are responsible for arriving on time, following captain and crew instructions, dressing appropriately for lake conditions, and bringing any personal items needed for comfort, including layers, sun protection, snacks, drinks, and towels when applicable.

Late arrivals may reduce time on the water and do not automatically extend the charter. The captain may end or adjust a charter if guest behavior creates an unsafe environment for passengers, crew, the vessel, or others on the water.

When evening timing drives your plans, compare our Chicago Sunset Sailing Charter and Chicago Fireworks Sailing Cruise.

For Playpen-style lake days, see the Chicago Playpen Sailboat Charter. Planning around an occasion? Start with special event charters, or view charter options.

Directions & Parking

meet us at Montrose Harbor

We operate exclusively from Montrose Harbor—please arrive 30 minutes before departure so we can brief safety and stow gear.
All departures

Montrose Harbor

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 directions

Chicago sailing charters · neighborhood guide

Montrose Harbor drive times from every Chicago community area

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

mark the dates that light up the harbor

Summer 2026 is built around fireworks weekends, the Air & Water Show corridor, long Playpen afternoons, and glassy sunset sails. Peak weekends book early.
  • Fireworks & holidays

    Navy Pier shows, July 4th week, and festival weekends—hold dates early for best slips.

  • Air & Water Show

    Captain-planned sightlines away from shore crowds; limited tickets on select vessels.

  • Playpen season

    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

partner with us on the water

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.