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We offer over 90 new boat models combined with a dynamic inventory of brokerage and trade-in boats that provides a boat option for anyone with any budget. Call to see what's available today. We are proud to rent Zar-Formenti rigid inflatable boats from Chicago's Belmont Harbor. These Italian R.I.B.s are fast, beautiful, and very safe. See the city from the water and have some fun! We offer powerboat classes for all ages and all levels of capability. Whether you are a beginner, want to earn your license, learn nighttime navigation or how to best manage rivers and locks - we have the class for you.

Wateriders offers unique Chicago kayak tours as well as premium kayak rentals. Since 1997, we have led thousands of adventurous people from all over the globe on recreational kayak tours in Chicago that reveal the history and magnificent architecture of our great city. Wateriders rents kayaks and offers public and private group tours including The Classic Chicago Kayak Tour, Shady Chicago/Ghosts & Gangsters Tour, Navy Pier Fireworks Paddle with its breathtaking views of the city skyline at night.

Chicago family-owned and operated since 1935, Wendella is Chicago's Original Architecture Tour®. Located at the start of Chicago's Magnificent Mile, our mission is to provide you with a comfortable, affordable, fun day on the waterways.

Pinnacle's fractional yachting and instruction programs have been a roaring success. In Chicago, the city of our origin, we have been entirely sold-out each year since our formation in 1998.

Urban Kayaks offers Chicago’s premier kayaking experiences on the Chicago River. We offer various trips based on any skill-level and group type. Make your reservation today.

Chicago Yachting charters a 40 foot Hunter sailboat out of Monroe Harbor, Chicago. We specialize in seasonal leases but also offer single day charters.

Anita Dee Yacht Charters specializes in hosting private and fully customized events aboard our yacht cruising venues.

We offer Private sails and power boat cruises for groups of up to 36 guests on one of our boats, and up to 11 guests on others. No matter what you are looking for, we can arrange it. Catering, special requests, arrangements for surprises, and unparalleled customer service. Check out our reviews on YELP and you will see why we can see we are the best sailing operation in the city. We also offer semi-private sailing for guests that want to share a sailboat with others. Our standard semi-private sails are Mon, Tue, Thu evenings, and Sat-Sun at 9am. All our boats are moored at slips, so when you arrive for your sail, you will park near our gate, and your captain will walk up the dock to the locked gate and bring you to your boat.

Pinnacle's fractional yachting and instruction programs have been a roaring success. In Chicago, the city of our origin, we have been entirely sold-out each year since our formation in 1998.

You board the Abby, club ship of the Columbia Yacht Club, permanently moored in Monroe Harbor, Downtown Chicago. The atmosphere is refined, yet casual. Elegant, yet homey. You're among friends in the most beautiful lakeside setting in the city.