Best results for
Sailing in Naperville, IL
Showing 1-12 of 12 results
Private Chicago Lakefront Sailing Cruise from Navy Pier
Sail Chicago’s lakefront on a private yacht with a captain, swimming and music on board
5.0 • 33 reviews
Chicago Sunset Skyline Sail From Navy Pier
Sail Lake Michigan for sweeping views of Chicago’s skyline
4.6 • 646 reviews
Romantic Chicago Sailing Charter
Share a peaceful Lake Michigan sail with Chicago skyline views
5.0 • 58 reviews
Private Sail & Swim Yacht Charter from Navy Pier, Chicago
Private Lake Michigan sailing with swimming, snacks, and a certified captain
5.0 • 33 reviews
Chicago Sunset Skyline Sail
See Chicago’s skyline from Lake Michigan on an evening sail
4.6 • 646 reviews
Chicago Sunset Sailing Charter
A quiet private weeknight sail with Chicago skyline views
5.0 • 58 reviews
Private Chicago Skyline Sunset Cruise on a 37' Sailboat
Sail Chicago’s lakefront at sunset aboard a private 37-foot yacht
5.0 • 33 reviews
Chicago Navy Pier Fireworks Cruise
Watch Navy Pier fireworks from the water with Chicago skyline views
4.6 • 646 reviews
Chicago Sunset Sailing Charter
Sail Lake Michigan on a private weeknight cruise with sunset and skyline views
5.0 • 58 reviews
Chicago Engagement Sailing Cruise
A private sail for proposals, photos, and a champagne toast
5.0 • 33 reviews
Cruise Chicago for Navy Pier Fireworks
Private 3-hour sail to view Navy Pier fireworks with a USCG-certified captain included
5.0 • 33 reviews