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 (a $260 value) from Chicago Sailboat Charters. Aquatic adventures depart Belmont Harbor at 7 p.m. Monday–Thursday and at 9 a.m. on Saturday and Sunday.
CSC’s experienced captains guide semi-private tours on a fleet of sailboats, two of which are new additions that measure 30–42 feet and were built by nondrunken sailors to ensure a safe and authentic journey. During a weekday nighttime sail, you and a comrade can glide along the darkened waters while admiring the lights shining from Chicago's landmarks, neighborhoods, and Great-Fire reenactments. Or, opt for a weekend-morning sail to swap a daily caffeine injection for invigorating views of Lake Michigan's shimmering water and stray moonbounces. The tours seat up to six, so grab a friend and four strangers, make a reservation, and hit Mother Earth's liquidy skin. Sail before June 5 to have the amusement tax waived. Customers who sign up for the newsletter before May 15 get a $25 credit toward any upgrade, $10 credit for any cancellation fees, and a lifetime supply of quiet satisfaction.
Although Chicago Sailboat Charters sometimes offers discounts, this Groupon still presents the best deal.
Chicago Sailboat Charters
The minds behind Chicago Sailboat Charters share their passion for the sailing experience by making waterborne adventuring accessible to the general public with group sailing charters. Fostering the atmosphere of a private charter, the captains ferry passengers out onto Lake Michigan for stunning views of Chicago's skyline. The crew encourages its guests to make the most of the trip by providing a bathroom, bottled water, ice for drinks, and plenty of cooler and storage space, while encouraging guests to bring their own, snacks, drinks, and an inflatable blanket for a picnic out on the lake.
141 W Diversey Pkwy.
Chicago, Illinois 60657Get Directions