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    1. Local experiences
    2. /Things to do in Chicago…
    3. /Water Activities
    4. /Sailing
    5. /Chicago 2-Hour Private Engagement Cruise
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    Chicago 2-Hour Private Engagement Cruise

    Celebrate your proposal or engagement with a private sail along the Chicago Lakefront

    5.0 stars• 27 reviews
    From$886incl. taxes and fees

    Duration

    2 hours

    Ideal For

    Up to 12 people

    Includes

    Private yacht, captain, snacks

    Highlights

    Plan a private two-hour cruise for a proposal, engagement photos, or time together on the water. Sail the Chicago Lakefront aboard a 37-foot luxury sailboat from Navy Pier Marina.
    • Sail privately with your loved one along the Chicago Lakefront
    • Capture engagement photos or plan your proposal from the water
    • Connect your music to the onboard Bluetooth surround-sound speakers
    • Bring your own food and beverages, including beer, wine, champagne, or hard seltzer

    What's Included

    • USCG-certified captain trained in First Aid and CPR
    • Private use of a permitted, insured 37-foot sailing yacht
    • Complimentary beverages and snacks
    • Complimentary champagne toast
    • Kitchenware, refrigerator, and bathroom
    • Bluetooth surround-sound speakers

    Know before you go

    • Complete the waiver sent in your confirmation email for every guest
    • Children under 18 must be accompanied by a parent or guardian
    • This cruise is not recommended for people with impaired mobility
    • Weather cancellations for lightning or high wind are decided one hour before departure and receive a full refund

    Cancellation Policy

    Cancel up to 2 weeks before departure for a full refund, or up to 48 hours before for a 50% refund. Full refund if the operator cancels due to lightning or high wind.

    FAQs

    Yes. Have every guest in your party sign the waiver for the engagement cruise.

    Yes. You may bring your own food and beverages, including beer, wine, champagne, and hard seltzer.

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

    Meeting details

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

    Experience provided by On A Boat Sailing
    Experience provided by On A Boat Sailing

    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

    Reference #GCDMM2

    Private Charter

    $886.94

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

    0

    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

    Had the best time! Loved sailing on Lake Michigan on this fancy sailboat. Captain Greg is super accommodating too, helping make the experience very smooth. We also picked up catering from Reunion on the Southeast corner of the pier. Definitely making it very easy to feed our guests! Can't wait to try again but it will have to be on a Wednesday or Saturday night so we can get some shots of the fireworks!

    Photo of Jonathan Garcia

    Jonathan Garcia

    June 24, 2026

    Review 1 of 1
    5/5

    Had the best time! Loved sailing on Lake Michigan on this fancy sailboat. Captain Greg is super accommodating too, helping make the experience very smooth. We also picked up catering from Reunion on the Southeast corner of the pier. Definitely making it very easy to feed our guests! Can't wait to try again but it will have to be on a Wednesday or Saturday night so we can get some shots of the fireworks!

    Photo of Jonathan Garcia

    Jonathan Garcia

    June 24, 2026

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