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Lake Michigan Sailing Charter in Chicago

Lake Michigan Sailing Charter (up to 6)

From: $1048
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Belmont Harbor - Chicago, IL

May through October:
3 Hour Charter
Sunday through Friday - 4:00 PM
3.5 Hour Charter
Sunday through Friday -12:00 PM
4 Hour Fireworks Charter
Wednesdays - 7:30 PM

  • Sit back, relax and enjoy the luxury of a private sailing charter as your captain sails you and you party across the beautiful Lake Michigan.
    • All Captains are USCG licensed
    • Luxury class, 39 foot sailboat is designed for a balance of comfort and performance
    • Enjoy stunning views of the Chicago skyline along the beautiful Lake Michigan
    • An opportunity for you to get away from the crowds and have a unique Chicago experience on Lake Michigan
    Full Description>
  • Enjoy a wonderful day in the lap of luxury as you sail gracefully in the wide open waters of Lake Michigan on a private skippered sailing charter.

    Sit back, relax and enjoy as your captain sails you and your party across Lake Michigan.

    Chicago sailing conditions can be calm or exciting. Whether you are looking for a romantic sailing trip for 2 or a day on the water with 5 of your closest friends, your captain will do everything possible to suit your sail to your wishes.

    Your stylish 39 foot luxury cruiser was designed for a balance of comfort and performance. Because of this design, the seating area in the cockpit is very large and there is a great deal of deck space. Able to sail in even the lightest of winds, as well as heavy conditions, this is the perfect ship for Lake Michigan pleasure sailing.

    The sailboat is also equipped with hot and cold running water, a swim platform and swim shower, large retractable canopy and cockpit seat cushions. The interior boasts large bathrooms, beautiful teak and holly floors, and more than ample cold storage for all your food and drinks.

    This is sure to be to an experience you and your friends will be talking about for a long time.

    Fireworks Sail: Every Wednesday from Memorial Day through Labor Day, Navy Pier puts on fireworks displays that last about 10-15 minutes. Note: To book a sail at this time, there is a 4-hour charter minimum.

    Key Info>
  • Essential Information

    • No prior sailing experience necessary
    • You may bring your own food and drinks including alcohol - except for red wine and other dark drinks that may stain the boat
    • No glass bottles except for white wine and champagne
    • Your captain provides all the paper plates, forks, knives spoons, cups, napkins, cooler space, drink cozies, tin foil, ice, etc. that you will need
    • Gratuity for your captain is included in the price of this experience


    The sail will last for 3-7 hours depending on the option selected. Note: Fireworks sails have a 4-hour minimum.

    Maximum Participants

    This is a private experience for your party of up to 6 people.


    This experience is only for those on the charter.

    Weather Dependent

    This experience is weather dependent. Always contact the experience provider with any questions regarding weather conditions.

    What To Wear

    Wear layered clothing, bring rain gear, and wear light colored, soft-soled, non-marking shoes. In addition, it is recommended to bring a hat, sunglasses, and sunscreen.

    Booking Information

    For this experience, it is recommended to request bookings at least 30 days in advance.

    Cancellation Policy

    Prior to scheduling/booking a date for this experience, Cloud 9 Living's standard return and exchange policy shall apply. Once you have received a booking confirmation, no cancellations are allowed. If you need to reschedule, you may do so up to 14 days prior to your booked date. Failure to appear on your booked date or to reschedule at least 14 days prior to your booked date will result in the loss of the value of your experience.

    Experience ID


    1. What should we bring?
      Bring your food and drink, and possibly some extra clothing (80 degrees on shore can cool on the lake with the wind in your face) and swimwear/towels if there will be swimming. Your captain provides all the paper plates, forks, knives spoons, cups, napkins, cooler space, drink cozies, tin foil, ice, etc. that you will need. There is even plastic stemware for your white wine or champagne.
    2. What should we avoid bringing?
      Red wines or any other dark staining liquid (like grape or cranberry juices, etc.), Glass of any kind above deck (white wine and champagne bottles can be kept below and poured into plastic cups), Hard-soled, dark-soled, or marking shoes (you may go barefoot if you don?t have boat friendly shoes), metal rivets or buttons on pants (they damage the boat), illegal substances.
    3. What kind of shoes are best to wear?
      Light colored, soft-soled, non-marking shoes (like deck shoes or top-siders) are best to wear. Some gym shoes are OK. Please don’t wear shoes such as loafers, which have hard soles and can damage the gel coat of the boat. Most inexpensive flip-flops are not good for boats as the charcoal black soles leave scuffs everywhere.
    4. Is there a bathroom on the boat?
      Yes, there is a fully functional bathroom (as well as a shower for that matter) with running water to wash up.
    5. Can we bring children on board?
      Of course!  Please make sure to let us know at the time of booking so that we can prepare accordingly.
    6. Can we bring alcohol on board?
      Yes, being whatever you like. Please avoid bringing glass bottles if you can (except for wine). Please note, if you show up intoxicated, or become excessively intoxicated during the sail, the sail may be cancelled at the captain's discretion, and you will be charged for the full amount of the sail. If you have further questions regarding this policy, please contact Cloud 9 Living.
    7. What about seasickness?
      It is very uncommon. The captain does a number of things to take precautions against it for you. If you are worried about it , you may want to take one of the over the counter medications 45 minutes before sailing.
    8. What if there is bad weather?
      If the weather is too rough to sail, there is lightning, or there is persistent rain, the charter will be cancelled. You will be able to reschedule directly with the captain or you can exchange for another experience with Cloud 9 Living.
    9. What if there is light wind?
      If there is not much wind, you will be able to motor sail to any destination (for example to Navy pier for the fireworks or just out for a swim and a tour of the shoreline).
    10. Can we go swimming?
      Swimming is allowed during full daylight hours in the open water away from the shoreline (given safe sea conditions - captain's discretion).
    11. Is gratuity included?
      Gratuity is not included, but is customary and appreciated if you enjoy the sail. Recommended gratuity is $30-$40 per hour, but is of course at your discretion.
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