Chicago Sunset Cruise
Sail into golden hour with uninterrupted Chicago skyline views. Perfect for date nights, proposals, and small-group celebrations on Lake Michigan.
Chicago Private Boat Charters & Sailing Experiences
Chicago’s best momentsstart on the water
Private boat charters and sailing lessons on Lake Michigan—sunset cruises, fireworks nights, Playpen days, and hands-on experiences, all led by a licensed captain and tailored to your group.
Montrose Harbor, Chicago
Sunset to Fireworks
Sunset sails timed for golden hour
Front-row views of Navy Pier fireworks
Built for Your Group
Private charters for small groups
USCG-licensed captain included
Explore Lake Michigan
Cruise the skyline, harbors, and Playpen
From casual sails to premium yacht experiences
Chicago Fireworks Cruise
Watch Navy Pier fireworks from the water with front-row views. Skip the crowds and enjoy a private, captain-led experience on Lake Michigan.
Chicago Playpen Charter
Anchor in Chicago’s Playpen and join the city’s most popular on-water scene. Swim, relax, and enjoy a private charter with your group.
Lake Michigan Cruise
Cruise Lake Michigan with open water, skyline views, and room to relax. Ideal for groups looking for a laid-back private boating experience.
Chicago Sailing Lessons
Learn to sail on Lake Michigan with hands-on instruction. Take the helm, trim sails, and build real confidence with a licensed captain.
Lake Michigan Scuba Trips
Explore Lake Michigan dive sites with guided, boat-supported scuba trips. Perfect for certified divers looking for unique freshwater experiences.