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. Today's Groupon carries on the tradition of keeping it real on the water. For $125, you get two seats on a 2.5-hour sail with Chicago Sailboat Charters (a $220 value). Choose the time for your sail from the following:

• Monday, Tuesday, or Thursday from 7 p.m. to 9:30 p.m.
• Saturday or Sunday from 9 a.m. to 11:30 a.m.

Even with daily activities as varied as going to work, driving across town, or selling stolen DVDs on street corners, land-based city experiences are sadly lacking in flavor and subtlety. Add some nuance and flair to your previously beached lifestyle and charter a sail with CSC. The company's sailboats measure 31 to 42 feet and are hand-built by non-drunken sailors, ensuring a safe and authentic journey. Experienced captains will guide the tours, which seat one to six, so grab a friend and four strangers, make a reservation online, and hit Mother Earth's liquidy skin. Groups of six will also have the option to sail on weekday mornings and must call CSC to schedule a time.

With today's Groupon, CSC offers two tour options. During the 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 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. Sailing season kicks off on May 22; most boats depart from Belmont Harbor.

Not valid on the weekend of the Air & Water Show

Reviews

Chicago Sailboat Charters has a five-star rating from nine Yelpers:

• The boat was very clean and comfortable, and we were lucky to sail on a very sunny day. Overall, a great experience. – ERIKA C.
• This is a great way to see Chicago and spend some time with friends, without having to do any actual work on the boat...We'll definitely be back for more sails. – Jen G.
• From the first contact until the end of our cruise, [the captain] was quick to respond to our requests. He's also very knowledgeable of sailing, Lake Michigan and the city of Chicago. – Logan C.