Sailing in River West

Select Local Merchants

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

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

The 35-foot Alpha Puppy and the 30-foot Sundog could be the names of two extremely long dachshunds, but they're actually the two boats comprising Offshore Adventures Chicago's fleet. Captain Rick, a USCG Master Captain, helms the boats on the company's Lake Michigan cruises, with routes that highlight views of the city's skyline. As he steers, passengers enjoy beverages they brought along and listen to their personal playlists rather than the music of a nearby seagull pecking its xylophone. During the summer, twice-weekly night cruises augment the typical cruise selections and offer spectacular views of the city's fireworks displays.

321 S. Sangamon #810
Chicago,
IL
US

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.

400 N Michigan Ave
Chicago,
IL
US

The history buffs of Chicago's Finest River Walk Tour lead engaging and dynamic tours of two very different parts of the city. During the summer, intimate groups of up to 15 traverse the various walkways of the bustling yet majestic riverfront or climb aboard a boat for a sunny river voyage, soaking in vistas of Chicago's many architectural wonders. In the winter, tourgoers head below the sidewalks with torch in hand to explore the troll-populated tunnels of the Pedway, Chicago's underground network of shops, hotels, train stations, and eateries. Regardless of the tour, the knowledgeable guides engage strollers in a two-way conversation about the Windy City, enlightening audiences with historical yarns and humorous anecdotes.

112 East Wacker Drive
Chicago,
IL
US

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.

111 East Lake Shore Drive
Chicago,
IL
US