$50 to Sail with Chicago Sailboat Charters ($90 Value)


23 Ratings

Value Discount You Save
$90 44% $40
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Limited quantity available
Over 600 bought

The Fine Print

Promotional value expires Sep 30, 2009. Amount paid never expires. Only 600 Groupons available $50 per person Must call to schedule sail Calling at least 7 days in advance is recommended to ensure availability Valid Fri-Sun 9-11:30am 6 people per boat maximum Not valid for Air & Water Show weekend Gratuity not included Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

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With today’s Groupon, $50 per person gets you a 2.5-hour sail with Chicago Sailboat Charters (a $90 value). It’s the perfect way to see the sights and relax on the lake for a fraction of the price of owning, storing, and constantly waxing a sailboat. Many of CSC’s boats comfortably hold six people, so buy a couple of Groupons, gather your friends, and head to the north end of Belmont Harbor to see if you can float. No sailing experience is necessary: Captain Marty will take care of all the sailing responsibilities while you and your friends kick back and enjoy yourselves. For more information about the sail, click here.

Most people experience the city on land. Whether going to work, driving across town, or selling stolen DVDs on street corners, there’s no opportunity to sit back and soak in all that’s Chicago. Even tourists commonly spend their time rushing from attraction to attraction without taking in the bigger picture. A sail with CSC, known for its private charters, provides a fresh perspective that even the oldest Chicagoan (Mary Higgins, 106) can appreciate.

All CSC sailboats measure 30 to 42 feet and are hand-built by sailors, so you can enjoy a worry-free time on the water. Bring some food for a picnic aboard CSC’s flagship sailboat, Lost, and take advantage of the many amenities, including:

  • An iPod connection so you can listen to your own tunes
  • Fresh running water
  • Padded cockpit seats for sailing comfort and flight simulation
  • A private space down below to change into something more comfortable
  • Plenty of deck space to stretch out in the sun
  • A swim ladder to easily get in and out of the water

CSC offers a bevy of other tour options, including sails during the 3rd and 4th of July, Mackinac Race Day, and spectacular full moon rises. Call ahead to schedule your morning sail between 9 a.m. and 11:30 a.m., Friday through Sunday. If you round up six friends, you can sail any morning of the week.

Don’t miss out on this great deal on Chicago water tourism, which has quickly become the city’s largest tourism industry (surpassing walking tourism and Segway tourism). It’s impossible to go a day without overhearing a water tourist yelling about Lake Michigan’s beauty: the crystal-clear waters, the white-sand shores, the miniature water tornadoes that dance across the sea like angry babies. People go to great lengths to sail beyond where sharks hunt children in order to make wishes by throwing coins into the water. Come visit Lake Michigan.


Chicago Sailboat Charters has only two reviews on Yelp, but those two people loved the experience and Captain Marty. Read their thoughts:

  • “From the first contact until the end of our cruise, Marty was quick to respond to our requests. He’s also very knowledgeable of sailing, Lake Michigan and the city of Chicago. Our sailing trip was a blast, I’d highly recommend Marty and Chicago Sailboat Charters.” – Logan C.
  • “I’ve been on five or six sails with Captain Marty over the past few summers, and I was happy with all of them. He was very accommodating regarding scheduling a time that would work for us, and always had the sailboat spotless and ready to sail when we arrived. Marty knows the areas of Lake Michigan around Chicago as well as anyone I’ve sailed with before, and did a great job of taking us to places on the water that weren’t too crowded while making sure that we had a comfortable sail regardless of weather conditions. I plan on booking more charters with Chicago Sailboat Charters, and I definitely recommend them to anyone who is looking for a fun, enjoyable day on Lake Michigan for an affordable price.” – Mark V.

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

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