Chicago Sailing Private Charter Sunset - 2 Hours (WEEKDAY)

Private Sunset Sail at Lake Michigan

Get ready for a magical evening on the water with this private sunset sail on Lake Michigan. Designed for up to six guests, this exclusive two-hour charter offers a front-row seat to one of Chicago’s most unforgettable views—the city skyline glowing as the sun dips below the horizon.

Inclusions:

• Enjoy a two-hour private weekday sunset sail on Lake Michigan for up to six guests.
• Relax while the experienced crew handles the sail—or try your hand at steering with guidance from your captain.
• Soak in panoramic views of Chicago’s legendary skyline.
• Cruise past architectural icons like the Sears Tower, John Hancock Center, and Lake Point Tower.
• Catch a glimpse of the dazzling Ferris wheel at Navy Pier.
• Licensed USCG Captain and experienced crew
• A spacious 36 ft. Catalina sailboat (Vessel name: Bernard)
• All taxes and Navy Pier Facility Fees included

Whether you’re celebrating a special occasion or just want a peaceful evening with your favorite people, this sail is the perfect way to unwind. You'll cruise past iconic landmarks like the Sears Tower, John Hancock Center, and Lake Point Tower, with the famous Navy Pier Ferris wheel making for a picture-perfect backdrop. The experience is both relaxing and interactive—kick back and enjoy the ride, or try your hand at steering with guidance from your seasoned captain.

Your sailboat for the evening is a beautiful 36-foot Catalina (Vessel Bernard), captained by a licensed USCG professional who’s there to ensure your sail is smooth, safe, and memorable.

This weekday experience runs on Mondays and Thursdays and departs at 7:00 PM from Navy Pier Marina in downtown Chicago. It includes all taxes and Navy Pier Facility Fees, but parking is not included.

No sailing experience is required, and guests of all fitness levels are welcome. Dress comfortably, and don’t forget a light layer—it tends to be cooler on the lake in the evenings.

Whether it’s a romantic date night, a mini celebration, or a just-because kind of outing, this private sunset sail offers the perfect mix of serenity, sightseeing, and skyline magic.

Book this Chicago Sailing Private Charter Sunset - 2 Hours (WEEKDAY) experience today!