$130 for Two and a Half Hours of Semi-Private Sailing for Two from Chicago Sailboat Charters (Up to $260 Value)

Chicago Sailboat Charters

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Customer Reviews

30 Ratings

100% Verified Reviews
All reviews are from people who have redeemed deals with this merchant.


Martha C. · 4 reviews TOP REVIEWER
Reviewed April 14, 2013
We enjoyed a lovely cruise out on Lake Michigan.


Katie T. ·
Reviewed October 7, 2012
Really fun, it was only the two of us and another couple. We were able to bring on drinks and food. The captain was very informative and polite. Would definitely go back again.


Crystal P. · 3 reviews TOP REVIEWER
· Reviewed August 12, 2017
Our evening was absolutely amazing! Rob was the perfect captain and made our sail enjoyable. We would definitely recommend sailing with them. We can't wait to come back and do it again!

What You'll Get

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.

The Fine Print

Promotional value expires Sep 4, 2011. Amount paid never expires. Limit 2/person. Season starts 5/21/11, reservations can be made starting 3/29 at 10am. Reservation required 10 days in advance, subject to availability. Must be 12 or older. Not valid on 7/4, 8/20, 8/21. Tax and gratuity not included. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

About 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.

By purchasing this deal you'll unlock points which can be spent on discounts and rewards. Every 5,000 points can be redeemed for $5 Off your next purchase.