Sailing gained popularity during the early '90s, when many rappers wrote songs about crossing large bodies of water using only samples from Queen’s “Under Pressure” 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 (a $260 value), which departs from Belmont Harbor at 7 p.m. Monday–Thursday and 9 a.m. Saturday and Sunday.
Chicago Sailboat Charters’ experienced captains guide semi-private tours on a fleet of sailboats measuring 30–42 feet in length. Two new additions, like every vessel in the fleet, were hand-built by nondrunken sailors, ensuring a safe and authentic voyage. During the weekday nighttime sail, customers 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 daily caffeine injections behind and wake up with views from Lake Michigan's waves, feeling the wind in one’s pants and admiring the shimmering water and stray moonbounces.
The tours seat up to six, so sailing pairs can make a reservation before hitting Mother Earth's liquidy skin. Cancellations due to inclement weather are determined less than 30 minutes in advance of the sail and sometimes as soon as the time of the sail, so guests traveling to Chicago may want to plan back-up activities in case.