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    1. Local experiences
    2. /Things to do in Chicago…
    3. /Water Activities
    4. /Sailing
    5. /Private Chicago Skyline Sunset Cruise on a 37' Sailboat
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    Private Chicago Skyline Sunset Cruise on a 37' Sailboat

    Sail Chicago’s lakefront at sunset aboard a private 37-foot yacht

    5.0 stars• 33 reviews

    Duration

    2.5 hrs

    Ideal For

    Up to 12 people

    Includes

    Captain, yacht, snacks

    Highlights

    Sail the Chicago lakefront as the sun sets and take in skyline views from the water aboard a private 37-foot yacht.

    • Explore Chicago’s skyline from the water at sunset
    • Bring your own food, beer, wine, champagne, or hard seltzers
    • Connect your playlist to the Bluetooth stereo system
    • Relax with kitchenware, a fridge, and an onboard bathroom

    What's Included

    • U.S. Coast Guard-certified captain
    • Private sailing yacht
    • Complimentary beverages and snacks
    • Kitchenware and refrigerator
    • Bluetooth stereo speakers
    • Swim platform, ladder, life jackets, flotation noodles, floaties, and towels

    Important details

    • All guests must complete a waiver before sailing
    • Children under 18 must be accompanied by a parent or guardian
    • Not recommended for people with impaired mobility
    • A separate captain fee applies for parties of 8 or more and is not included in the listed price

    Cancellation Policy

    Cancel up to 2 weeks before departure for a full refund, or up to 48 hours before for a 50% refund. Full refunds for lightning or high-wind weather cancellations are at the operator's discretion.

    Product ID: K3F7B4

    FAQs

    Yes. Every guest in your party must sign a waiver before the cruise.

    Bring a rain jacket or layers for cooler days. Wear boat shoes, sandals, or tennis shoes with non-black soles.

    Yes. Bring your own food and beverages, including beer, wine, champagne, or hard seltzer, for your sunset sailing cruise.

    Meeting details

    Navy Pier Marina, 797 E. Grand Ave., Chicago, IL 60611

    Experience provided by On A Boat Sailing

    Related locations

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Private Charter

    $1,025.94

    Up to 7 guests for base price - Up to 12 guests for additional fee

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    What people are saying

    Review 1 of 5
    5/5

    We booked a sunset boat cruise for our dad’s 60th birthday and it was amazing! Greg was a great captain and it was such a memorable evening.

    Photo of Julie G

    Julie G

    July 20, 2026

    Review 1 of 1
    5/5

    We booked a sunset boat cruise for our dad’s 60th birthday and it was amazing! Greg was a great captain and it was such a memorable evening.

    Photo of Julie G

    Julie G

    July 20, 2026

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