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Real Pirates of the Inland Seas: Chicago Pirate-Themed Sailboat Tour

Chicago, United States

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Number of travelers
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Free Cancellation
up to 24 hours in advance
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icon1 hour 15 minutes  (Approx.)
iconOffered in: English
Good for avoiding crowds


Experience Lake Michigan from a perspective rare to visitors and locals alike on a pirate–themed sailboat tour. Your guides tell true but little–known stories about pirates, battles, and treasure hunts as you cruise past sweeping views of the Chicago skyline. Relax on deck while or join your guides for an interactive experience—the flexibility of the tour makes this a popular choice for families with children.
  • Choice of several departures throughout the day
  • Ideal choice for families
  • Step back in time on a history tour
  • Fully narrated tour
  • Seasonal Offer
Saved to wishlist!
Local taxes
Live commentary on board
Alcoholic drinks (available to purchase)
Food and drinks

Departure Point

600 E Grand Ave, Chicago, IL 60611, USA

Return Details

Returns to original departure point
  • Confirmation will be received at time of booking
  • Children must be accompanied by an adult
  • Minimum drinking age is 21 years
  • Refunds will not be issued if tour/activity is missed due to late or non-arrival of cruise ship
  • Not wheelchair accessible
  • Service animals allowed
  • Near public transportation
  • Most travelers can participate
  • This tour/activity will have a maximum of 148 travelers
  • OPERATED BY Windy of chicago Inc, DBA: Tall Ship Windy

For a full refund, cancel at least 24 hours in advance of the start date of the experience. Learn more about cancellations.

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
What is the maximum group size during Real Pirates of the Inland Seas: Chicago Pirate-Themed Sailboat Tour?
This activity will have a maximum of 148 travelers.

See all safety measures taken by Real Pirates of the Inland Seas: Chicago Pirate-Themed Sailboat Tour.


40 Reviews
1 star
Reviews by Viator travelers
Showing 1-2 of 40 reviews
Hey matey
, Jun 2018
Awesome story telling and cruise. This was my first time on lake michigan and also first time on a sailboat.
We really enjoyed this sail. Pirate...
Ryan T
, Jun 2017
We really enjoyed this sail. Pirate Dave (the greatest pirate you've never heard of) entertained us with stories of pirates on Lake Michigan and Chicago. He was humurous and insightful! the water and views of Chicago were beautiful. The crew was skilled and fun to watch. A nice relaxing tour!

Product code: 35169P3

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