Summer is here, pandemic restrictions are finally lifting, and there’s no better way to celebrate freedom and warmth with long days on the water. Whether you’re into getting a party boat on Lake Michigan, spending an afternoon kayaking the lakefront, or viewing the city's coolest buildings along the river—there’s a Chicago aqua-adventure calling your name.  

With so many options to choose from, we’ve gone ahead and rounded up 6 of the most bucket list-worthy water activities to experience this summer.

Chicago Skyline Sail Aboard Tall Ship Windy

Live your best Pirates of the Carribean fantasy in the famed Tall Ship Windy! You’ll explore Chicago’s gorgeous shores with a scenic trip around the great Lake Michigan, take in the world-famous skyline, and enjoy a full bar in the aft salon of Windy. And if it suits you better—check out their select firework night cruises.  

Where: Navy Pier – Tall Ship Windy 600 E Grand Ave Chicago IL 60611
When: Offered daily May - September, each sail is 75 minutes

Paddleboard or Kayak on the River & Lake Michigan

Chicagonians can cruise the lakefront, or tour the architecture of the city along the river, all from their own personal vessels whenever the summer adventure-urge calls. Urban Kayaks offers access to both the Chicago Riverwalk and Lakefront locations, with options ranging from twilight and sunset paddles, and “happy hour” paddles that include a domestic brew. 

Where:
Lakefront Location: 110 N. Lakeshore Dr / Chicago, Il 60601
Riverwalk Location: 435 E. Chicago Riverwalk / Chicago, Il 60601

Take a River Tubing Day Trip (with Transportation from Chicago!)

Grab your friends, pack your towel and remember your sunscreen. You’re going tubing! This outdoor experience is a full day trip with a Sourced Adventures Guide, and includes a 2 hour bus ride from Chicago to reach the Tippecanoe river. There you’ll pick up your included tube rental—and, may we suggest, a rented cooler float full of beer cans and plenty of water—and commence a two hour relaxing float!

Where: Pickup and dropoff from 100 W Randolph St, Chicago, IL 60601
When: Leaving in the early afternoon to return to the city 6:00 PM/ 6:30 PM

FLASH SALE: Use code BUCKETLIST for $10 OFF through Friday, June 18

Lake Michigan Party Boat Cruise

Bring up to a dozen of your friends to cruise Lake Michigan in the ultimate Party Boat. Enjoy their bluetooth sound systems, beer pong and flip cup tables on deck, and (if you get the 3 hour cruise) don’t forget to hop out and swim, to enjoy all the experience has to offer! All cruises are BYOB, with fireworks cruises available Wednesdays and saturdays. 

When: 3 Hour and 90 minute Captained Charter. Reservations start May 15, 2021 and go all summer long!
Where: Dock is just North of the Chicago Yacht Club, 400 East Monroe Street, Chicago, IL 60603

Private Yacht Charters

Ever imagine you’d be choosing between a “Sport,” “Premium” or “Luxe” full-service yacht rental with your friends—at approachable prices? Neither did we, but Knot My Boat  charters break the mold. 

Their sport boats alone feature all the essentials for family gatherings and river cruises: three entertainment zones, a cabin area including a bedroom/living area, kitchenette, and one bathroom, and a bluetooth sound system. Just remember to tip the world-class hospitality crew when you return to the real world  land! 

Where: 3155 S Lake Shore Drive Chicago, IL 60616
When: Various Dates and Times Available.