Private Lake Michigan sailing with swimming, snacks, and a certified captain
Sail Chicago’s lakefront at sunset aboard a private 37-foot yacht
A private sail for proposals, photos, and a champagne toast
Cruise Chicago’s waterfront with a professional crew and private gathering spaces
Celebrate on the Gypsy Spirit along Chicago’s waterfront
Sail Lake Michigan for sweeping views of Chicago’s skyline
See Chicago’s skyline from Lake Michigan on an evening sail
Watch Navy Pier fireworks from the water with Chicago skyline views
90-minute group sail for Navy Pier fireworks and Chicago skyline views
Double-decker catamaran for private entertaining and water views
Relax together with a flybridge lounge, wide walkways, and onboard music
Private cruising for relaxed gatherings and celebrations
Private yachting for celebrations, family gatherings, and corporate outings
Enjoy a Chicago charter with a USCG-licensed captain and 15+ years of experience
Hire a Polish-speaking captain for your rented Lake Michigan boat
Hire a Chicago captain and cruise to the Playpen, Monroe Harbor, or the river
Hire a US Coast Guard licensed captain for your Chicago boat day
Cruise the water with a captain for relaxed outings, playpen visits or evening fireworks
Captain for hire on Lake Michigan, with payment options and holiday rates
Hire a Chicago captain for a Lake Michigan outing
Cruise Chicago by private boat with an experienced captain
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.