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

    A private sail for proposals, photos, and a champagne toast

    5.0 stars• 27 reviews

    Duration

    2 hrs

    Ideal For

    Up to 12 people

    Includes

    Captain, snacks and beverages

    Highlights

    Set sail along the Chicago Lakefront for a proposal or engagement photo session with city views from the water. Enjoy private time together aboard a 37-foot luxury sailboat.

    • Plan a proposal or engagement photo session against Chicago Lakefront views
    • Celebrate together with a complimentary champagne toast
    • Connect your music to the Bluetooth stereo system
    • Bring your own food and beverages, including beer, wine, champagne, or hard seltzer
    • Purchase alcohol on board or add catering and special requests for an additional fee

    What's Included

    • U.S. Coast Guard-certified captain trained in first aid and CPR
    • Private sailing yacht
    • Complimentary beverages and snacks
    • Kitchenware, refrigerator, and bathroom
    • Bluetooth stereo system

    Important details

    • Complete a waiver for every person in your party before departure
    • A parent or guardian must accompany anyone under 18
    • Not recommended for people with impaired mobility

    Cancellation Policy

    Full refund up to 2 weeks before departure; 50% refund up to 48 hours before. Full refund if the operator cancels due to lightning or high wind.

    Product ID: GCDMM2

    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

    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

    $866.94

    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

    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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