Discover Chicago from the water with Vagabond Sunset Sails. This 3-hour sunset cruise offers stunning skyline views and a tranquil escape on Lake Michigan, perfect for small groups or couples seeking a memorable outdoor experience.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
3 hours
Fitness Level
No special fitness level needed; suitable for most ages and abilities.
Wildlife
History
Lake Michigan has been central to Chicago's development as a port city since the 19th century.
Conservation
Vagabond Sunset Sails adheres to eco-friendly practices, including proper waste disposal and respecting wildlife.
Two Brothers Sailing Chicago
Discover Chicago from the water with Vagabond Sunset Sails. This 3-hour sunset cruise offers stunning skyline views and a tranquil escape on Lake Michigan, perfect for small groups or couples seeking a memorable outdoor experience.
Two Brothers Sailing Chicago operates private sailing charters on Lake Michigan from Chicago, Illinois. The company offers a selection of excursions aboard the yachts Vagabond and Drifter, providing small-group experiences that showcase Chicago’s skyline, Museum Row, and Navy Pier.
Trips range from two to six hours and include dedicated three-hour sunset charters that depart along the city front. Options include Vagabond Sunset Sails, Vagabond / Cityscape Sails, Sunset Sail & Stay with an overnight aboard the Vagabond for up to six people, Drifter Sunset Sails, and Drifter / Cityscape Sails. Most cityscape charters follow a route from Museum Row to Navy Pier to maximize skyline viewing and waterfront perspectives.
Two Brothers Sailing Chicago focuses on personalized private charters for small groups seeking a memorable outing on Lake Michigan. Booking information, trip durations, departure points, and specific availability are provided through the business’s reservation process. The company’s itineraries emphasize the visual highlights of Chicago’s lakeshore, including close views of the skyline at sunset and evening city lights for overnight guests.
For travelers seeking a water-level vantage of the Windy City, Two Brothers Sailing Chicago offers curated sailing experiences that combine Chicago waterfront sightseeing with the leisure of a private charter. Many charters depart from the lakefront near Museum Row, offering direct access to lakefront routes. Reservations are required and available through the company’s online booking channels, and confirmation emails are sent after booking.
Location
Chicago, IL
Operating on Lake Michigan
Tours Offered
5 Trips
Sunset, cityscape, overnight options
Trip Length
2–6 hrs
Short to extended charters available
Overnight Option
Yacht Stay
Overnight aboard Vagabond available
Reserve a sunset sail, cityscape cruise, or overnight yacht stay aboard Vagabond or Drifter — limited private charters available.
Check the weather forecast
Wind and weather conditions can change quickly on Lake Michigan, so dress appropriately and confirm sailing times before heading out.
Bring layers and sunscreen
Evening temperatures can drop after sunset, and sun protection is still important during daytime hours.
Arrive early for the best seats
Getting to the dock a bit early ensures a prime spot on the boat for optimal views and photos.
Capture sunset moments
Bring your camera or smartphone to snap stunning shots of the Chicago skyline at dusk.
Sunscreen
Protect your skin from UV rays during daytime hours.
summer
Casual clothing and layers
Dress comfortably and add layers to stay warm during cooler evenings.
spring,fall,winter
Camera or smartphone
Capture the scenic views and memorable moments.
Sunglasses
Shield your eyes from the sun and glare on the water.
spring,summer