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Chicago events and adventures


Our safety record is impeccable and our charter captains are fully trained and licensed. You are guaranteed to have a sailing adventure with captains and crew that are all accomplished Lake Michigan sailors excited to share their love of adventure sailing and the water, with a passion for entertaining new passengers and friends in Chicago. We love seeing our friends return year after year! Each sailing adventure is conducted by one of our licensed captains with the duty of keeping their passengers safe and entertained on beautiful Lake Michigan. We may be the captain, but when you sail with us, we let you take the helm. We encourage you to be yourself unless you want to be a pirate then always be a pirate! Chicago events and adventures

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8 thoughts on “Chicago events and adventures”

  1. We pride ourselves on offering a wide selection of adventure, including small boat rentals, luxury yacht charters and sailing lessons. Chicago Loop Alliance launched the placemaking initiative in , making the season its fifth annual.

  2. Each sailing adventure is conducted by one of our licensed captains with the duty of keeping their passengers safe and entertained on beautiful Lake Michigan. We may be the captain, but when you sail with us, we let you take the helm.

  3. Chicago Loop Alliance launched the placemaking initiative in , making the season its fifth annual.

  4. Each sailing adventure is conducted by one of our licensed captains with the duty of keeping their passengers safe and entertained on beautiful Lake Michigan.

  5. We pride ourselves on using ALL of our sails, not just revving an engine and calling it sailing in Chicago. The event series transforms alleys and other urban locations into creative exhibition spaces that bring artists and the public together for an evening of exploration, interaction and celebration of the arts.

  6. Our safety record is impeccable and our charter captains are fully trained and licensed. We love seeing our friends return year after year! Each sailing adventure is conducted by one of our licensed captains with the duty of keeping their passengers safe and entertained on beautiful Lake Michigan.

  7. You are guaranteed to have a sailing adventure with captains and crew that are all accomplished Lake Michigan sailors excited to share their love of adventure sailing and the water, with a passion for entertaining new passengers and friends in Chicago. We love seeing our friends return year after year! Two Brothers Sailing Adventures is your Chicago sailing destination.

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