$35 for a Two-Hour Cocktail Skyline Sail from Tall Ship Red Witch, LLC ($70 Value)

Central Chicago

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In a Nutshell

Passengers sip cocktails on a tall ship while taking in nighttime views of Chicago's iconic skyline

The Fine Print

Expires Jul 31st, 2013. Limit 1 per person, may buy 1 additional as gift. Limit 1 per visit. Valid only for option purchased. Reservation required. Must book sail online by 6/30/13. 24hr cancellation notice required. Must be 18 or older. Must sign waiver. Customers may bring food on-board but no drinks. Tall Ship Red Witch has the right to reschedule any tour with less than 20 passengers on board. Subject to weather conditions. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

Boat captains must master nautical lexicon before sailing the seas to ensure that they can distinguish port, which means left, from starboard, which means launch the vessel into deep space. Count down to a sea launch with this Groupon.

$35 for One Ticket To a Cocktail Skyline Sail ($70 Value)

On two-hour cocktail skyline sails, passengers sail along the shores of Lake Michigan beneath the night sky on a 77-foot topsail wooden tall ship. Click here to view upcoming cruise dates. Cruises may be booked online, but you can reach Tall Ship Red Witch, LLC by email at ChicagoRedWitch@gmail.com.

Tall Ship Red Witch, LLC

What looks like a crimson-hulled pirate ship glides into view from behind Shedd Aquarium. The wind picks up, surging into the schooner's 77-foot gaff-rigged sails and speeding the vessel along Lake Shore Drive at 8 knots. Those on shore can just make out the boat's name, Red Witch, and what appear to be passengers raising a drink to the Chicago skyline.

Designed by renowned naval architect John G. Alden and named after the book Wake of the Red Witch—the same story that inspired the film starring John Wayne and Gail Russell—the Coast Guard–licensed ship accommodates up to 49 passengers within its mahogany-over-oak frame. Having sailed waters off Maui and San Diego, the boat now docks at Burnham Harbor and is under the stewardship of Captain Andrew Sadock and his crew who will be glad to autograph cannonballs for each passenger.

Outdoor activities, from cycling to sailing