$130 for Two and a Half Hours of Semi-Private Sailing for Two from Chicago Sailboat Charters ($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.


Crystal P. · 3 reviews
· 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!


Stuart L. · 1 review
· July 9, 2017
Great activity. Captain was friendly and great sailor. Got lucky with impeccable weather. Lots of fun and would definitely do again.


Greg L. · 3 reviews
September 15, 2015
Be early, bring extra warm clothes and be ready for a great time on the water. Excellent Captains, Rob and Cory!

What You'll Get

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.

The Fine Print

Promotional value expires Sep 4, 2011. Amount paid never expires. Limit 2 per person. Limit 1 per visit. 10 day cancellation notice or up to $125 fee may apply. Must be 12 or older. Not valid for 7/4/11, 8/20/11, or 8/21/11. 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.