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

94% of 17 customers recommend

Give as a Gift
30 bought
Limited quantity available

In a Nutshell

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

The Fine Print

Expiration varies. Limit 3 per person, may buy 1 additional as a gift. Limit 1 per visit. Valid only for option purchased. Online reservations required 10 days in advance. Subject to weather. Fee of $10 to $85 may apply for cancellations. Must be 12 or older. Must sign waiver. Not valid 7/4 or 8/16-18. 2.5-hour sail option valid until June 28, 2013 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)

All sails through July 15 are two and a half hours, and sails between July 16 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.


94% of 17 customers recommend

  • “We enjoyed a lovely cruise out on Lake Michigan.”

Outdoor activities, from cycling to sailing