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Lake Michigan Sailing Charter (up to 6)

Chicago, IL

Item #: WAT-CHI-0023
Option & Pricing:

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Please select an option above.

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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!
Belmont Harbor - Chicago, IL
When Do I Choose A Date?
If giving as a gift, your recipient can choose a date at their convenience; otherwise, you can choose one after checkout.

May through October:
Daily - 8:30 AM, 11:30 AM, 3:30 PM, & 7:00 PM

Option & Pricing:
Please select an option above.
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.
Experience Provider Info
Complete information for your Experience Provider, including contact information, will be included on your booking confirmation email once you or your gift recipient have scheduled the experience. Our Product Management team handpicks top-rated experience providers, removing the guesswork for you and ensuring your peace of mind.
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.
What should we bring?

Bring your own 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.

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.
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.
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.
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.
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.

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.
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).
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).
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.

Experience Vouchers that have not been redeemed can be returned hassle-free within 30 days.  All refunds will be made to the original purchaser.

Experience Vouchers that have not been redeemed can be exchanged for anything else in our marketplace at any time.  If you choose to exchange for an experience that costs more, you'll simply have to pay the difference.  If you choose to exchange for an experience that costs less, you'll have a credit towards your next booking with Cloud 9 Living.

Cancellation Policy

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.

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based on 1 reviews.
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