Sailing gained popularity during the mid-'90s, when many rappers wrote songs about crossing large bodies of water using only a baggy T-shirt as the sail and killer flow as wind. Carry on the tradition of keeping it real on the water with today’s Groupon: for $130, you get two seats on a two-and-a-half-hour sail from Chicago Sailboat Charters (up to a $260 value), which departs from Belmont Harbor at 7 p.m. Monday–Thursday and 9 a.m. Saturday and Sunday.

CSC’s experienced captains guide semi-private tours on a fleet of sailboats, two of which are new additions, that measure 30 to 42 feet and are hand-built by nondrunken sailors, ensuring a safe and authentic journey. During the weekday nighttime sail, you and your comrades will glide along the darkened waters, admiring the lights shining from Chicago's landmarks, neighborhoods, and five-alarm fires. With the weekend-morning sail, leave your daily caffeine injection behind and wake up with views from Lake Michigan's waves, feeling the wind in your pants and admiring the shimmering water and stray moonbounces. The tours seat up to six, so grab a friend and four strangers, make a reservation and scope out their newsletter online, and hit Mother Earth's liquidy skin. Customers who sign up for the newsletter before March 31 will have their 9% amusement tax waived and are eligible for free upgrades and a lifetime supply of quiet satisfaction.