Is this trip suitable for children?

Yes, the sunset sail is family-friendly and suitable for children, though all guests should be accompanied by an adult.

What should I bring onboard?

Bring sunscreen, a hat, layers for warmth, and a camera to document the experience.

Are there restroom facilities on the boat?

Yes, Vagabond is equipped with restroom facilities for guest convenience.

Can I bring alcohol onboard?

Alcohol is not permitted unless arranged in advance as part of a special package.

How many people can fit on the yacht?

Vagabond accommodates up to six guests comfortably.

What happens if the weather is bad?

The trip may be rescheduled or refunded in case of severe weather, prioritizing safety.

Water Activities & Sunset Sail with Two Brothers Sailing Chicago | Lodging | Boat Tour

Chicago, Illinois, stands as an iconic hub of architecture and vibrant city life, but its scenic beauty extends far beyond its urban skyline. The Sunset Sail & Stay with Two Brothers Sailing offers a rare chance to experience the Windy City's stunning waterfront from the deck of a luxurious yacht. Departing from Chicago Harbor, this adventure takes guests from the hustle and bustle into a tranquil sunset cruise along Lake Michigan, where the city’s skyscrapers cast dramatic reflections on the water. As the sun dips below the horizon, the sky ignites with hues of orange, pink, and purple, creating a perfect backdrop for unforgettable photos.

This trip isn’t just about the sunset—it includes an overnight stay aboard Vagabond, a beautifully maintained yacht that offers comfort and elegance. The boat features cozy cabins, panoramic views, and a lullaby of gentle waves, giving guests a chance to unwind in style after a day of motoring through the lake. By night, the city lights shimmer across the water, transforming Chicago into a glittering tableau. The vessel’s stable, smooth ride makes for an excellent experience whether you're an avid sailor or a first-time boat-goer.

What makes Two Brothers Sailing unique is their commitment to crafting tailored experiences that blend adventure with relaxation. Their crew emphasizes safety and quality, ensuring guests enjoy both the scenic cruise and amenities onboard. This trip is perfect for celebrating special occasions or simply escaping the concrete jungle for a few hours of waterborne serenity.

Whether you're a local seeking a new perspective, or a visitor craving a memorable escape, the Sunset Sail & Stay provides a captivating mix of nature, city charm, and maritime luxury. It’s a prime example of how Chicago’s waterfront offers more than just views—it's an experience that stays with you long after the boat docks.

Highlights include panoramic lake vistas, a quiet night under a starlit sky, and the invigorating feeling of sailing on one of the Great Lakes. With flexible packages for small groups, this adventure promises a unique glimpse into Chicago’s waterscape unlike any other.