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.
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.
Ian Jacobson, the founder of Chicago SUP and Wakeboard Chicago, grew up on the Lake, and started his board-top paddling program after his passion for the sport ignited during a trip to Hawaii. His love for the low-impact activity also feeds his interest in its safety; as he spreads awareness of the sport, he makes sure customers know when it's safe to venture out into calm or choppy water. His passionate team gathers a range of paddling certifications, such as ACA and WPA, and many staffers are equipped with official training in first aid and CPR as well as unofficial training in blowing bubbles. Some of the team honed their boarding skills on the waves of California and Hawaii, and several boast a background in stand-up paddleboard yoga and fitness instruction.
Dubbed "the epicenter for the paddle community in Chicago" by Chicago Now, Chicago SUP ignites Jacobson's passion for the sport of standup paddleboarding in others with rentals and instruction atop calm waters boasting sweeping skyline views. As shoulders, backs, and arms work to propel the boards forward under his instruction, the core engages to keep balance on the board, resulting in a full-body workout enlivened with the pleasure of sunny skies and the thrill of submarine sightings in Lake Michigan. The company was featured on NBC Chicago's 1st Look and in the Chicago Tribune, grabbing Jacobson attention for pioneering the relaxing full-body workout in the Midwest, as well as for their innovative board-top yoga classes (SUPyo) and SUPFit classes. In the 2013 Expedition Paddle Series, he and his team point paddlers toward attainable goals as they paddle decked in headlamps toward Navy Pier for fireworks, or simply take in the skyline at sunset or the full moon above.
Paddle and Trail is an independently owned outdoor retailer and outfitter with 4 locations in Northern Illinois and Southern Wisconsin specializing in paddlesports, cycling, nordic sports, hiking and trail running, and adventure racing. We sell and rent kayaks, canoes, and bike. We offer paddle trips and classes.