Adrenaline CH17040IC

Chicago Sailing Private Charter Sunset - 2 Hours (WEEKDAY)

The Most Romantic Sail on Lake Michigan!

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  • Chicago Sailing Private Charter Sunset - 2 Hours (WEEKDAY)
  • Chicago Sailing Private Charter Sunset - 2 Hours (WEEKDAY)
  • Chicago Sailing Private Charter Sunset - 2 Hours (WEEKDAY)
  • Chicago Sailing Private Charter Sunset - 2 Hours (WEEKDAY)

When the sun sets, the magic starts. Drifting along Lake Michigan in a stunning sailboat, you and yours experience what’s undoubtedly The Windy City’s most romantic views.

Item: CH17040IC
Monroe Harbor (Chicago)
Available Dates
Our Price: $ 508 2025-11-28
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  • Description

    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!

  • Rated 4.6/5 based on 11 customer reviews
  • Experience Details

    Fitness and Experience

    • No particular level of fitness or experience is required.

    What to Bring/Wear

    • Confirmed Adrenaline trip notes and Valid ID
    • Dress for an active adventure.
    • Shorts and pants are preferable to skirts and dresses due to wind.
    • Dress according to the weather conditions.
    • The temperature is typically cooler on the lake, especially at night. Consider bringing an extra layer for warmth.

    What is Supplied

    • 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

    More Information

    • Departs at 7PM
    • This is a private charter. The passenger list is at your discretion
    • All charters are non-smoking
    • Can take up to 6 passengers included in the price
    • Please make the booking under just one persons name
    • Weekend sails available with a surcharge - see other packages
    • The charter departs from Navy Pier Marina in downtown Chicago. Full meeting and check-in instructions will be provided after booking.

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Location

Monroe Harbor (Chicago)