On A Boat Sailing offers a refined yet easygoing way to experience Chicago from the water. Departing from Navy Pier Marina, they specialize in private luxury sailing charters for small groups, with over 25 years of sailing experie...
On A Boat Sailing offers a refined yet easygoing way to experience Chicago from the water. Departing from Navy Pier Marina, they specialize in private luxury sailing charters for small groups, with over 25 years of sailing experie...
Had the best time! Loved sailing on Lake Michigan on this fancy sailboat. Captain Greg is super accommodating too, helping make the experience very smooth. We also picked up catering from Reunion on the Southeast corner of the pier. Definitely making it very easy to feed our guests! Can't wait to try again but it will have to be on a Wednesday or Saturday night so we can get some shots of the fireworks!
Jonathan Garcia
June 24, 2026
Had the best time! Loved sailing on Lake Michigan on this fancy sailboat. Captain Greg is super accommodating too, helping make the experience very smooth. We also picked up catering from Reunion on the Southeast corner of the pier. Definitely making it very easy to feed our guests! Can't wait to try again but it will have to be on a Wednesday or Saturday night so we can get some shots of the fireworks!
Jonathan Garcia
June 24, 2026