Semiprivate Sail or Season of Sailing for Two from Chicago Sailboat Charters (Up to 62% Off). Three Options Available.

North Side

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In a Nutshell

Captains ferry groups of up to six onto Lake Michigan for relaxing excursions and stunning views

The Fine Print

Expiration varies. Amount paid never expires. Limit 3 per person, may buy 1 additional as a gift. Limit 1 per visit. Valid only for option purchased. Reservations required online 10 days in advance. Subject to weather. 10 day cancellation notice required or fee up to $85 may apply. Must be 12 or older. Must sign waiver. Not valid 7/4 or 8/16 - 8/18/13. 2.5-hour sail option valid until 6/28/13 only. Must use promotional value in 1 visit. 9% Chicago amusement tax not included. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

Ancient sailors used to navigate by consulting the North Star, until it lost its way during its twenties and decided to just head west to see what happened. Enjoy modern sailing with this Groupon.

Choose from Three Options

  • $99 for a semiprivate sailing excursion for two, valid until June 28 (a $259 value)
  • $129 for a semiprivate sailing excursion for two, valid until August 31 (a $259 value)
  • $649 for a season pass for two, valid through August 31 (a $1,299 value)<p>

All sails through June 28 are two and a half hours, and sails between June 29 and August 31 are two hours. Semiprivate sails are shared and will include up to six passengers. The sails take place on Monday, Tuesday, and Thursday at 7 p.m., as well as Saturday and Sunday at 9 a.m. Season passes are good through August 31 for five semiprivate sailing excursions—two standard sails, one fireworks upgrade sail, and two weekend upgrade sails—plus as many last-minute sails as are available. See more information about upgrades here.

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

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!
Crystal P. · August 12, 2017
Great activity. Captain was friendly and great sailor. Got lucky with impeccable weather. Lots of fun and would definitely do again.
Stuart L. · July 9, 2017
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

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.