EXPERIENCES ARE OPEN & OPERATING!
- COVID-19 Updates
-
Shop By Location
- Alaska
- Alabama
- Arkansas
-
Arizona
-
Colorado
- Connecticut
- Washington DC
-
Georgia
- Hawaii
- Iowa
- Idaho
-
Illinois
-
Indiana
-
Kentucky
-
Louisiana
-
Massachusetts
-
Maryland
- Maine
-
Michigan
-
Minnesota
-
Missouri
- Montana
-
North Carolina
- Nebraska
- New Hampshire
- New Jersey
- New Mexico
-
Nevada
- New York
- Oklahoma
-
Oregon
-
Pennsylvania
- Rhode Island
-
South Carolina
- South Dakota
-
Tennessee
- Vermont
-
Washington
- Wisconsin
- West Virginia
- Wyoming
- eGift Cards
- Gift Ideas For Him
- Gift Ideas For Her
- Gift Ideas For Couples
- Corporate Gifts
- About Us
- My Account
- Logout
- REDEEM VOUCHER
- LOOKUP BOOKING
-
CLOSE
Creating Memories Since 2005
EXPERIENCES ARE OPEN & OPERATING!
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!
From: $1048
Overview
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!
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 evening 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.
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
Duration
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.
Spectators
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?
What should we avoid bringing?
What if there is bad weather?
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.
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.
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.
Returns
Experience Vouchers that have not been redeemed can be returned hassle-free within 30 days. All refunds will be made to the original purchaser.
Exchanges
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.
How It Works...
1
Choose from
1,900+ Experiences
2
E-Voucher
Delivered Instantly
3
Your Recipient Books
Their Experience
4
Create unforgettable
memories!
Other Chicago Experiences
Our Promise to You: Hassle-Free Gifting
At Cloud 9 Living, we believe in delivering amazing experiences—and your gifting experience should be no different. That’s why we ensure worry-free gifting for both the giver and recipient with these extra benefits and guarantees:
Easy Returns & Exchanges + No Expiration Date
All vouchers that have not been redeemed can be returned hassle-free within 30 days—free of charge, no questions asked.
Even after the 30-day return window closes, you can exchange your voucher for anything else in our marketplace at any time. If you choose an experience that costs more, you'll simply have to pay the difference. If you choose an experience that costs less, you'll have a credit towards your next booking with Cloud 9 Living. And our vouchers never expire!
Our Price Guarantee
Not only do we curate the best experiences for you, we also guarantee that you'll pay the same price through Cloud 9 Living as you would buying directly from our experience providers. Plus, you get the benefit of our flexible policies, convenient shopping experience, and exceptional customer support with no added costs.
If you find the same experience with the same provider advertised at a lower standard price (does not include vendor promotions or sales), simply contact us at (866) 525-6839 or email us at info@cloud9living.com and we’ll match the advertised price.
Instant E-Voucher
With instant e-voucher delivery, we make it easy to find and give the perfect gift fast—even if you’re shopping at the last-minute. You’ll be able to send an amazing experience to your loved one immediately for instant gratification for you and your recipient.
Our Price Guarantee
Not only do we curate the best experiences for you, we also guarantee that you'll pay the same price through Cloud 9 Living as you would buying directly from our experience providers. Plus, you get the benefit of our flexible policies, convenient shopping experience, and exceptional customer support with no added costs.
If you find the same experience with the same provider advertised at a lower standard price (does not include vendor promotions or sales), simply contact us at (866) 525-6839 or email us at info@cloud9living.com and we’ll match the advertised price.
Gift Voucher or Book?
If you are giving this experience as a gift and would like your recipient to be able to choose a date at their convenience, click Buy Gift Voucher.
If you'd like to select a date now and book this experience, click Book Experience.