Sailing in Forest Park


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  • Urban Kayaks
    Brothers Aaron and Asher Gershenzon and friend James Morro grew up in the city, but always possessed a passion for the outdoors. They practiced wilderness kayaking for most of their lives before earning their American Canoe Association certifications on Lake Superior. Each of them brings dual passions for their home city and outdoor sports to the company’s guided group and private kayak trips. Guided paddles change on every outing as guides blend downtown architectural commentary and little-known gangster stories with tie-ins to current events. Though each guide tells different stories, often interspersed with humor, all of them focus on environmentally friendliness. Paddling trips utilize a fleet of lime-green Confluence Watersports kayaks, and staffers often wear lime-green shirts—all of which render them easily identifiable from the riverwalk, but well camouflaged in supermarket produce sections. Up to four guides lead groups of 15 kayaks or less and prepares them with a briefing on paddling techniques, rules of the river, and assurances of the stability of their wide recreation kayaks. The guides' watchful eyes and constant advice have instilled confidence in even the most unsure participants, When not guiding trips, staffers extend their easygoing atmosphere to their office—nestled across the river from the Centennial Fountain's Water Arc—where the storefront lies amidst the bustling city that surrounds it. Inside the shop, the owners' much-beloved pooches frolic around a hanging hammock.
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    270 Chicago Riverwalk
    Chicago, IL US
  • Go Sailing Chicago
    Gliding across Lake Michigan, the sailing party watches the sun sink beneath the Chicago skyline. As the last rays fade from view, the city's skyscrapers throw their light onto the lake's surface. The captain steers the ship past Grant Park and Millennium Park, and then veers out toward Navy Pier, where the ship's passengers find a prime viewing spot for the Saturday-night fireworks show. In addition to charters like these, the captains of Go Sailing Chicago—all holding US Coast Guard Master Captain licenses and certifications from the American Sailing Association and US Sailing—furnish beginner through advanced sailors with sailing gloves and life jackets before leading hands-on instruction in proper seamanship. Launching from DuSable and Monroe Harbor, and sometimes other points along the lakeshore, Go Sailing Chicago's four-boat fleet meets or exceeds the safety standards set down by the USCG and the most persnickety of ship-in-a-bottle builders.
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    400 East Monroe Street
    Chicago, IL US
  • Wendella Sightseeing Boats
    Wendella’s boats have sailed Chicago’s waters since 1935, when founder Albert Borgström built the company’s first ship by hand. Still run by Albert’s great grandson, Michael, the company complements its time-tested architecture and history tours with specialty tours that feature beer and barbecue, wine and cheese, or fireworks. Wendella also operates Chicago’s distinctive yellow-and-black water taxis.
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    400 N Michigan Ave
    Chicago, IL US
  • Kayak Chicago Chicago
    The hustle and bustle of the city can’t touch the calm waters of Lake Michigan. There, on gently rolling waves surrounded by fresh breezes, Kayak Chicago hosts tours and lessons, and lets paddlers take to the waters on their own with rentals. Captained by Dave Olson, a kayaker for more than 20 years and outdoor educator for more than 10, the company entrusts certified instructors and guides with shaping the strokes of kayaking newbies. Their tours take aquatic explorers out on the lake at night to ooh and ahh over summer fireworks or along the Chicago River to survey the city’s renowned architecture and map out their next bank heist. The staff also plants patrons on standup paddleboards for introductory lessons or wave-top rounds of SUPYoga or SUPPilates.
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    1220 W. LeMoyne Ave.
    Chicago, IL US
  • Tall Ship Red Witch
    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.
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    600 E Waldron Dr.
    Chicago, IL US
  • Tall Ship Adventures of Chicago
    A modern recreation of a 19th-century schooner, the 148-foot-long Windy bears us back ceaselessly into the past. During regular demonstrations, the crew unfurls the sails and casts off into the lake. Guests often assist with onboard tasks, and the variety of tours includes events such as ghost stories and sunset excursions.
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    600 E Grand Ave.
    Chicago, IL US

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