This company offers a wide variety of sailing times and prices to fit most pocketbooks, including lunch or brunch sailings.
We spent our tenth anniversary on this boat, and it was just perfect. Two bands play on different floors, one offering listening (Jazz) and one to dance to (light rock). I wasn't ready to leave after the 3-hour time limit! I just can't tell you how magical the Chicago skyline is on a summer night on a boat in the lake! Fairies must be at work here!
The only thing you might want to address is seating arrangements for dinner. We wanted to be alone, and had to plead and beg to be seated at a table for two instead of 6! It would have been ok under other conditions, but for a special night we wanted to be alone. They were very gracious, and did accommodate us.