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.
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.
Situated near Chicago Avenue at the Chicago River, Wateriders' experienced and knowledgeable guides have been leading relaxed kayak tours down Chicago’s picturesque waterways since 1997. Day and night tours explore the city's most exciting attributes, focusing on history, architecture, and eerie mob chronicles as guides provide paddling instruction and share true tales of Al Capone's mythical collection of tracksuits. Wateriders also rents its kayaks to independent paddlers who prefer to discover Chicago's sights on their own.
MunkyBoards' electronic skateboards carry riders on four-wheeled adventures throughout the city at speeds of up to 18 miles per hour. Available in two sizes with different power capabilities, boards can travel as far as 9 miles before they need to recharge—just like clown cars powered by other drivers' fear. Mushc like the boards themselves, designs draw inspiration from both futuristic imagery and contemporary transportation; decks on the shorter boards feature imagery inspired by the coveted hoverboard from Back to the Future Part II, and larger decks sport a map of the CTA's train system.
According to Wheel Fun Rentals’ website, they “were green before green was popular.” Founder Brian McInerney and his staff back up this claim by pairing renters with recreational modes of transportation that are safe for the environment. Visitors can rent a canopied surrey to navigate the trails near Foster Beach or a mountain bike to traverse Lake Michigan Mountain. Single- and double-kayaks allow one to glide over the water and take in the sweeping skyline to the south.