All private bookings are approved for up to 7 guests with the option to upgrade to 12 guests for an additional fee- please inquire!

Per U.S. Coast Guard laws, our charters with more than 7 guests are considered a recreational (formerly bareboat) vessel, and we cannot legally provide you a captain. If booking for more than 7 guests you will receive a list of current approved captains for hire, as well as instructions on how to reach out. Alternatively, if you would like to supply your own captain, please email info@onaboatsailing.com with the captains credentials.

Yes, a USCG-certified Captain is included for parties of up to 7 guests in the price at checkout. Gratuity for the Captain of 10-20% of the charter cost is appreciated for exceptional service!

Per U.S. Coast Guard laws, our charters with more than 7 guests are considered a recreational (formerly bareboat) vessel, and we cannot legally provide you a captain. If booking for more than 7 guests you will receive a list of current approved captains for hire, as well as instructions on how to reach out. Alternatively, if you would like to supply your own captain, please email info@onaboatsailing.com with the captains credentials.

It is often very difficult to predict the conditions on the Lake as they can be very different compared to the city and surrounding suburbs of Chicago.

We do our best to communicate expectations of poor weather ahead of your sail. We will sail in the rain and advise guests to dress accordingly or request to reschedule when possible.

If there is current or forecasted lightning or high wind, we will make a weather cancellation one hour before your scheduled departure.

If your charter is cancelled, we will contact you and offer a delay, rescheduled booking or a refund that aligns with our booking policy.

We have a recommended age minimum of 5 years old. Children under 12 will be encouraged to wear a life jacket at all times.

We love having kids onboard, but please be advised of the risks of boating and the range of conditions from smooth sailing to rough and choppy waters. It is 100% the parent's responsibility to monitor children and ensure that they stay within designated safe areas of the boat. Conditions will be unstable at times!

We do not encourage bringing pets on board without prior boating experience.

If you do wish to bring a cat or small to medium sized dog we encourage you to bring a pet life jacket. We do not provide pet life jackets. Of course a parrot on the shoulder is always welcome on the high seas, arrrr matey!

Lake Michigan is subject to a wide range of conditions, from calm to rough seas depending on the weather which will cause the boat to be unbalanced at times.

As such, some passengers may experience seasickness. Please see below for our tips to prevent seasickness:

• Be well rested and do not drink alcohol excessively the night before

• Take antiemetic drugs (Dramamine) the night before to get it in your system and

again 30 minutes before the cruise

• Be sure to have plain foods ahead of the cruise. An empty stomach or foods

that do not sit well (greasy, spicy, dairy etc.) are not good ideas

• Wear an acupressure wristband such as sea-band

Yes of course!

Our sailing experiences for perfect for all forms of celebration.

We are happy to discuss special needs ahead of your booking date & time. We provide catering, provisioning and or decorations for an additional fee, too.

Yes, you and your crew will have full access to our in-cabin bathroom.

Remaining 50% will be automatically charged 5 days in advance of the booking date to the card on file unless otherwise paid in advance. Please call ahead to make other payment arrangements if the card on file is not the preferred method.