Chicago Sailboat Charters


23 Ratings

Value Discount You Save
$260 50% $130
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Over 380 bought

In a Nutshell

  • Semi-private sailing trip
  • Available on weekends
  • Amazing views
  • Tours seat up to six people

The Fine Print

Promotional value expires Sep 4, 2011. Amount paid never expires. Limit 2 per person. Limit 1 per visit. Reservation required 10 days in advance; subject to availability and weather. Must be 12 or older. 10 day cancellation or fee up to Groupon price may apply at appointment. Not valid for 7/4, 8/20, or 8/21. Tax included for those who sail by 6/5/11. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

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.

Customer Reviews

23 Ratings

Be early, bring extra warm clothes and be ready for a great time on the water. Excellent Captains, Rob and Cory!
Greg L. · September 15, 2015
Great experience
Randi R. · September 15, 2015
We enjoyed a lovely cruise out on Lake Michigan.
Martha C. · April 14, 2013
Merchant Location Map
  1. 1


    141 W Diversey Pkwy.

    Chicago, Illinois 60657

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