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Chicago Sailboat Charters - North Side

First-Class Sailing for Two or Six from Chicago Sailboat Charters (Up to 50% Off)

The Fine Print

  • Expires Sep 15th, 2014.
  • Limit 1 per person, may buy 2 additional as gifts. Limit 1 per visit. Must sail by expiration date on your Groupon. Reservation required. Must sign waiver. Not valid for July 3/4 evenings or Aug 16-17 daytime sailing. Sailing takes place Monday, Tuesday, and Thursday evenings at sunset, or Saturday and Sunday mornings. All children must be 12 or older.

Questions and Answers 2 questions


Greetings ~ If I purchase for two, should I assume you will try to fill the other 4 spots, or will the sail be private? If the plan is to fill the remaining 4 seats, what happens if you don't?

Christiane M.  asked on  Apr 2, 2014


Hi, our first -class semi-private sails are typically filled on every sailboat. Since multiple sailboats participate , if there are 4 vacancies, they will be spread across 2 boats, so it is very unlikely that any sailboat will have 4 empty seats. Cheers

Captain Marty .  from  Merchant  replied on  Apr 2, 2014


Is there space available for Sunday June 15, 2014 for a group of 6 people.

Lauren H.  asked on  Mar 31, 2014


Yes, there is availability for June 15, and you can check ALL current availability at and click on Availbility. If you don't see a sail there listed for the size group you have, ask us and we will see if we can probably one. Thanks

Captain Marty .  from  Merchant  replied on  Mar 31, 2014

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