top of page

Frequently Asked Sailing Questions

Have you ever wanted to sail but were unsure what it would cost to charter a private yacht? If so, Windy City Sailing is here to help with all your sailing–related questions. We have made things easy to find by categorizing our questions, and if there’s anything you can’t find, feel free to reach out. Our knowledgeable staff is here to answer all your questions about sailing along the wonderful Chicago Lakeside. From planning the perfect corporate outing for out of town guests to helping you witness the incredible 4th of July fireworks, we have it all covered!

View of bareboat charter on Windy City Sailing

What is your cancellation policy?

We have a seven (7) day cancellation policy. Cancellation within seven (7) calendar days of your reservation will result in forfeiture of your deposit. Cancellation outside of seven (7) calendar days of your reservation and the deposit will be refunded less a $50.00 service fee. Review our cancellation and rescheduling policies

What is your rescheduling policy?

Our rescheduling policy is very simple: Reschedule within seven (7) calendar days of your reservation and there is a $100.00 rescheduling fee. Reschedule outside of seven (7) days of your reservation date and there is a $50.00 rescheduling fee. Review our cancellation and rescheduling policies

What happens if there is bad weather?

We must respect Mother Nature and will not put anyone in danger. If it’s raining, lightning, hailing, or just too rough to sail, we will reschedule your group for a future date or provide a full refund. The weather in Chicago can change in a flash, so we typically wait until the last minute to cancel a charter. We keep an eye on the NOAA Radar website

Do I need to make a deposit when booking a sailing charter?

Yes, we require a 50% deposit for all charter reservations. Review our cancellation and rescheduling policies

What types of payment do you accept?

Windy City Sailing accepts all major credit cards.

Please note that we legally cannot accept payment on behalf of your hired captain/crew as they are separate contractors that are hired by the Charterer. We suggest you reach out to your hired Captain to discuss their preferred payment method. Captains are not employed by nor affiliated with Windy City Sailing.

Reservations, Changes, Confirmations

Location, Parking, What to bring

Where are the yachts located?

The Windy City Sailing yachts are at the North end of Belmont Harbor.

Belmont Harbor is on the North Side of Chicago, 5 miles north of downtown.

Our Vessels are on the “G” dock. The address to the North End of Belmont Harbor is 400 W Belmont Harbor Dr, Chicago, IL 60657.  Please use this address for Uber, Lyft, GPS, and Taxi Services.


Can I park my car at Belmont Harbor?

Parking is provided by the City of Chicago at $14 per day.  Payment is accepted via credit card at automated kiosks.

What should we bring along?

We recommend that you bring a jacket for evening sails. It’s also in your best interest to take a peek at the weather and dress accordingly. Offshore breezes can be cool at times. Don’t worry if you forget your jacket because we have a few extras on the boat. Sunscreen is always a good idea, but we do not allow oil or spray sunscreen on the boat.  Don’t forget the camera. Check the weather conditions in Chicago.

What refreshments can we bring? Is alcohol permitted?

Feel free to bring any type of beverages and food. Full sailors are happy sailors, so enjoy. We supply plates, glassware, flatware, napkins, wine opener, bottled water, and a cooler stocked with ice. If you need to purchase something nearby, Whole Foods close by on Halsted & Waveland.  Review our cancellation and rescheduling policies

What kind of shoes should I wear?

Non-marking shoes are allowed, or just take off your shoes while onboard.  We ask you not to wear dress shoes with dark marking soles.

The Sailing Experience

How do I find a Captain?

After booking, Windy City Sailing will provide you with a list of approved Captains approved by our team that are familiar with our vessels. Captains are independent contractors that are employed/hired freely by the Charterer. Captains are not affiliated with nor employed by Windy City Sailing.

Is there a bathroom on board?

Yes, we have two bathrooms onboard our yachts. We take pride in providing you with an immaculate and safe sailing vessel.

Can I help with sailing the yacht?

The captain will handle everything but if you are interested just ask to take the wheel! The captain and crew will always be there to ensure your safety.

How far into Lake Michigan will we sail?

We usually sail along the lakefront as requested by our clients. The sailing distance into the lake will depend upon the wind and the length of your charter.

Will my cell phone work on the lake?

Yes, most cell phones on major networks will work within three miles of the Chicago Lakefront.

Who is our captain and what are his/her qualifications?

All Windy City Sailing captains are USCG (United States Coast Guard) licensed with extensive experience along the Chicago Lakefront. Also, all captains and crew are enrolled in mandatory drug testing programs.

Do you supply a cooler onboard?

Yes, we have a built-in refrigerator and large freezer for your food and drinks.  We will stock the icebox with two bags of ice for your use.  We ask that you leave any coolers you bring with you at the dock.

Can I drive the yacht?

Yes, you can be as hands-on as you like once the captain is out of the harbor. Of course, the captain is always in charge.

Can we go on the river?

Unfortunately, no. The Nebula’s sail is too tall to fit under the bridge to go up the river.

How much does a Captain Cost? Do I Tip?

Captain’s typically command $75-110 per hour before gratuity. 
It is customary to leave a gratuity to your hired Captain/Crew for 15-20% of the total charter price (not to be confused with the Captain’s hourly rate).  Payment & gratuity can be provided directly to your hired Captain.

Can we play our own music?

Yes, our vessel is equipped with premium bluetooth sound systems.

Frequently Asked Questions: Miscellaneous

Are children allowed to sail?

Yes, children love to sail, just let us know their ages/size so that we have the correct personal flotation devices available.  They can take a wheel as well!

Can we bring dog(s)?

We love our furry friends, but more times than not, we enjoy the sailing experience more than they do. We kindly ask you to refrain from bringing your pooches along.

Have we answered all of your questions? If not, please call or email us so we can respond to your questions.


bottom of page