Chicago Sailing

What is included in a Chicago Sailing experience?

Your Chicago Sailing trip typically includes a professional licensed captain, a well-maintained sailing yacht, safety briefing, and all required onboard safety equipment. Guests can relax, enjoy skyline views, and experience Lake Michigan from a unique perspective.

Where do Chicago sailing trips depart from?

Most Chicago Sailing departures leave from Monroe Harbor or DuSable Harbor, both located along Chicago’s waterfront near downtown. Exact meeting points are provided after booking and may vary depending on the vessel and experience selected.

Do I need sailing experience to join a Chicago sailing tour?

No sailing experience is required. All Chicago Sailing trips are led by experienced captains who handle navigation and boat operation. Guests are welcome to relax or, in some cases, participate in light sailing activities under guidance.

What should I bring on a Chicago Sailing trip?

It is recommended to bring weather-appropriate clothing, sunscreen, sunglasses, and a light jacket, as conditions on Lake Michigan can change quickly. Soft-soled shoes are also ideal for safety and comfort on deck.

What landmarks can I see while sailing in Chicago?

During a Chicago Sailing trip, you may see iconic landmarks such as the Willis Tower skyline, Navy Pier, Adler Planetarium, and the Chicago shoreline. Evening sails also offer exceptional views of the city lights reflecting off the lake.