easy
3 hours
No special fitness level needed; suitable for most ages and abilities.
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.
Groups of 1 - 6 people | 3 Hour Sunset Charter
Embark on a captivating 3-hour sailing adventure along Chicago's stunning waterfront. Experience the city's iconic skyline from the serene waters of Lake Michigan, gliding past Museum Row and Navy Pier. This unique charter offers an unforgettable perspective of Chicago's beauty, perfect for small groups seeking a memorable outing.
Charters starting at $400 Groups of 1 - 6 people
3 hour charter
See the beautiful sights – Sail the city front from Museum Row to Navy Pier as you view Chicago from the best angle: the waters of Lake Michigan.
Wind and weather conditions can change quickly on Lake Michigan, so dress appropriately and confirm sailing times before heading out.
Evening temperatures can drop after sunset, and sun protection is still important during daytime hours.
Getting to the dock a bit early ensures a prime spot on the boat for optimal views and photos.
Bring your camera or smartphone to snap stunning shots of the Chicago skyline at dusk.
Lake Michigan has been central to Chicago's development as a port city since the 19th century.
Vagabond Sunset Sails adheres to eco-friendly practices, including proper waste disposal and respecting wildlife.
Protect your skin from UV rays during daytime hours.
summer specific
Dress comfortably and add layers to stay warm during cooler evenings.
spring,fall,winter specific
Capture the scenic views and memorable moments.
Shield your eyes from the sun and glare on the water.
spring,summer specific