Kayaking in Highland Park

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Founder Rick Sweitzer started the adventure travel company in 1983 before leading one of the first amateur dogsled expeditions to North Pole. Driven by his vision, the guides and instructors of The Northwest Passage lead travelers of all skill and fitness levels to some of the most dramatic terrain on the planet. Locally, the team leads outings around the Chicago area, ranging from stand-up paddleboarding classes on Lake Michigan to kayaking and camping trips in Door County, Wisconsin. As for the rest of the world, Northwest Passage sends it adventurers to conquer it locale by stunning locale during programs that include hiking across Europe, trekking to remote Polar regions, and dressing up like scientists to infiltrate Area 51.

1760 Tower Road
Winnetka,
IL
US

With an armada of kayaks, canoes, and stand-up paddleboards at their command, Midwest Paddlesport Adventures' team spearheads expeditions to bodies of water across Northern Illinois and Southern Wisconsin. Frequent trips include calming floats down the Fox River––which is densely populated by local wildlife––and Lake Andrea, a former quarry characterized by local rocks. The expert navigators safely guide groups to their destinations, pointing out animal tracks and majestic waterfowl and they commute to the office.

2205 Birch Lane
Rolling Meadows,
IL
US

Situated on Bangs Lake, Wauconda Boat is a full-service marina with certified and master technicians on staff. In addition to renting out paddleboards, kayaks, and pontoon boats, Wauconda Boat can also supply boat motors, parts, and mermaid repellent.

231 E Liberty St
Wauconda,
IL
US

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.

270 Chicago Riverwalk
Chicago,
IL
US

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.

1501 N Magnolia Ave
Chicago,
IL
US

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.

950 North Kingsbury Street
Chicago,
IL
US