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 Al Capone 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.
One guide leads six participants and prepares them with a briefing on paddling techniques, rules of the river, and assurances of the stability of their wide-river kayaks. The guides' watchful eyes and constant advice have instilled confidence in even the most unsure participants, including basketball player Andre Iguodala, who slowly grew accustomed to his kayak by the end of his session. When not guiding trips, staffers provide their single and tandem kayaks to customers who want to explore the river on their own. They extend their easygoing atmosphere to their office—nestled across the river from the Centennial Fountain's Water Arc—where picnic tables stand by the storefront, and the owners' chocolate Labrador frolics inside around a hanging hammock.
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.
In 1935, Albert Borgstrom, a Swedish immigrant and carpenter by trade, set about constructing a 65-foot wooden yacht. He named the ship The Wendella and charged visitors $0.25 to ride through the city and listen to a guide expound on the sights. This simple vessel ended up being a steppingstone, and 75 years later, guests still ride along, now craning their heads back at the jagged opalescent silhouette of Trump Tower and the beehive curves of Marina City. Beneath the evolving skyline, the fleet has expanded to six vessels, which are now run by Albert's grandson, Michael Borgstrom. Wendella staffs a dedicated, in-house education department to keep the city's history alive and make sure that people continue to believe in water so it doesn’t disappear. On special excursions, the crew stocks the boats with wine for tastings beneath the stars or points the vessel through the verdigris waters of the lake to watch evening fireworks shows.
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 down the Chicago River at night to ooh and ahh over summer fireworks or during the day 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.
The massive schooner gently bobs in the Lake Michigan waters as the Chicago skyline towers on the shore. Onboard, hardy sailors relate tales of piracy and the rumrunners who filled the city's speakeasies as they train their passengers to tie knots and unfurl sails. Period lessons abound onboard Windy, the lone vessel helmed by US Coast Guard-certified captains and crews. The nostalgic steed is used to educate visitors on the lake's maritime traditions and explore coastal waters. Windy also plays host to themed adventures that include fireworks shows, pirates explaining city architecture, and pirates complaining about the popularity of pool noodles. Crews strive to make each tour unique, with sailors who expound on their skills as well as performers and educators versed in history, maritime lore, art, and theater.
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.