Cruise Chicago’s lakefront for skyline and Navy Pier views
Cruise and swim aboard a spacious Sea Ray with room to lounge
Pilot a 2-person Craig Cat and cruise the Chicago River skyline
Paddle past the Wild Mile and Chicago's skyline in a single or double kayak
Cruise Chicago’s river in a vintage 1950s Milo Craft
Paddle the Chicago River and learn downtown architecture in 3 hours
Paddle the Chicago River past the Wild Mile and downtown skyline
Paddle Chicago River routes in a single or double kayak
Build foundational kayaking skills on calm Chicago River waters
Paddle Goose Island and downtown as Chicago lights reflect on the river
Cruise the Chicago River for 2 hours on a private, self-drive pontoon
Take the wheel on a 22 ft pontoon cruise on the Chicago River
Cruise Chicago by private 47 ft yacht with space for up to 12 guests
Private 6–8 hour fishing charter for up to 6 on Lake Michigan
Sail Lake Michigan for Chicago skyline views and Navy Pier fireworks
Sail Chicago’s lakefront on a private charter with time to swim and relax
Sail Lake Michigan at sunset for Chicago skyline views from the water
Build practical sailing skills aboard a 26-foot Chris-Craft on Lake Michigan
Choose your paddlecraft for a self-guided outing on the water
Explore Chicago River routes by kayak or stand-up paddleboard at your own pace
Learn paddleboard skills for calm-water adventures
Anchor at Chicago’s Playpen for swimming, skyline views, and a laid-back day on the water
Clarity is geology, not luck: quartz sand, seagrass filtration, and how close the Gulf Stream runs. Thirteen beaches, and the trade-off each one asks of you.
Florida issues no boating license at all. What the marina checks is a safety education card, and whether you need one comes down to one date: January 1, 1988.