CHICAGO'S PREMIER ​PRIVATE SAILING CHARTER

What should I wear?
Dress for an active adventure. Shorts and pants may be preferable to skirts and dresses because of the wind. Also remember to dress appropriately for the weather. It does tend to be a little cooler on the lake, especially at night, so consider bringing an extra layer.

What kind of footwear is appropriate?
A standard sneaker or boat shoe is a great choice. Bare feet are also appropriate!
Heels, dress shoes, flip-flops, and boots are not appropriate and you may be asked to remove them before boarding the sailboat.

Is smoking allowed on the sailboat?
No. Smoking, vaping, or the use of any tobacco products is NOT allowed on board any of our vessels.​​

Is alcohol allowed on the sailboat?
Yes, you are allowed to bring a reasonable amount of alcohol on board for your consumption provided that by doing so, you are not in violation of any federal or state laws.  We ask that you please avoid bringing glass containers aboard whenever possible, but understand that sometimes a bottle of champagne is necessary!

Can I bring my pet dog, cat, snake, or fish?
No. Unfortunately we cannot accommodate animals of any type.

May I cancel or reschedule my sail?
You may cancel or reschedule your sailing charter up to 48 hours prior to your scheduled departure without penalty.  If you cancel/reschedule your charter within 48 hours of your scheduled departure you will be charged a percentage of the cost of your charter as a cancellation/rescheduling fee as follows:

• 50% cancellation/rescheduling fee if the cancellation is made less than 48 hours before your scheduled departure.
• 100% cancellation/rescheduling fee if the cancellation is made less than 2 hours before your scheduled departure.
• No-shows will be charged a 100% cancellation fee.

Should I tip the captain/crew?
As with any service industry, gratuity for good service is always appreciated and typically ranges from 15-20%.

What happens if we are late for our scheduled sail?
Your sail may be shortened by the amount of time you are late and you will be charged the full charter fee.

How many people can you accommodate?
We can accommodate a maximum of 6 passengers in addition to the captain and crew.

Is there a minimum age allowed on the boat?
There is no minimum age requirement for private charters. However, if you are going to have any passengers in your party that weight less than 40 lbs. please call us at the time of booking so that we are sure to have the appropriate safety equipment on board.

What if the weather looks bad?
If it is safe for sailing, we will sail, even in a light, summer rain. We cannot control the weather, but we can harness it for some fun sailing! We will provide you as much advance notice as possible in the event that your sail must be postponed or cancelled due to weather. Our captains keep a close eye on the weather forecasts and ultimately have full discretion on appropriateness and safety of the sailing conditions.

Can I fish from the sailboat?
No. Fishing is not allowed.

​Can I swim from the sailboat?
Swimming may be permitted on charters of 3 hrs or longer during daylight hours only.  Swimming is not guaranteed and is at the captain's discretion. If permitted by the captain every passenger on board will be required to sign a waiver & release prior to anyone swimming.  SWIMMING IS AT YOUR OWN RISK!​

Can we bring food on board the sailboat?
Yes. Food that can be eaten with your hands is usually easiest.

Is there a place to keep food and drinks cold?
Yes, there is a refrigerator on board for your use.

Is there a bathroom on board the sailboat?
There is a bathroom on board, however, the flushing mechanism on the toilet can be tricky to use and a little temperamental. To avoid any situations that could become embarrassing, we encourage you to use a bathroom on shore.

Is there a private area for changing?
Yes. There is a cabin down below with a door for your privacy. You are also welcome to change in the bathroom.

Where do we meet the sailboat?
We sail out of Monroe Harbor which is located just east of the intersection of Monroe Street and Lake Shore Drive. Our pickup spot is on the north side of the harbor along the “MONROE HARBOR CHARTER WALL”.  It’s a short walk from the intersection of Monroe Street and Lake Shore Drive to our pick-up / drop-off spot.

From the intersection, walk east towards the lake. When you pass the Divvy Bike Station rack, turn left and head north until you are standing at the water's edge. Walk along the water's edge as it curves to the east. Continue walking passed the cement pier. Our pickup spot is east of the cement pier. Our sailboat will have a big blue feather flag with the name "Come Sailing" flying from the stern.

​If you happen to pass a large ship with a blue hull named Abegweit, you have walked too far.

​Google Map

Click on the sailboat icons for the names and descriptions of the pickup locations