Tipping is purely optional and always appreciated by our staff. While we are reticent to suggest an appropriate gratuity, instructors commonly receive tips in the range of $20- $50 range for exemplary service. Charter captains typically receive 16%-20% of the charter cost as a gratuity.  Tips can be added to any credit card transaction. If you experienced service below your expectations, please inform our management team.

There are 2 national organizations that certify instructors and sailing schools: US Sailing and the American Sailing Association (ASA). US Sailing has long been the governing body for the sport of sailing in the United States, representing the United States in all international sailing events, including the Olympics. The USSA certification process is acknowledged to be the most rigorous and most consistent in America. US Sailing is a non-profit organization, overseen by a volunteer governing board of America’s leading sailors. For more information regarding US Sailing’s accreditation process for schools and their certification system, please visit their website. American Sailing Association is a for-profit organization that promotes the sailing instruction industry. ASA affiliated schools are given considerable discretion over performance standards and instructional requirements.

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The first rule of sailing is Be Prepared. All Chicagoans know how quickly the weather can change. No matter what the temperature onshore is, it will feel at least 10 degrees cooler once you are out on Lake Michigan. We Highly Recommend that you dress in layers that are capable of protecting you from chilly conditions or sun. Your unneeded clothing can always be stowed aboard the boat. A windbreaker/raincoat is advisable in all but mid-summer conditions. Fleece clothing is more comfortable than cotton. Don’t forget the sun protection (UV block, lip balm, hats, visor, etc), water, and snacks. We sell bottled water at our dock.

For your safety and comfort, Chicago Sailing requires that you wear shoes at all times. While boat shoes are not mandatory, any footwear must provide sound footing and must have non-marking soles (to tell if your soles are non-marking scuff your foot on a wood or tile floor). Please do not wear flip flops or high heels. If you are uncertain about the appropriateness of your shoes, please call prior to arrival.

You are welcome to bring your own food and drink as long as it is appropriately consumed and cared for. While alcoholic beverages are not allowed during class activities, you may enjoy them responsibly during rentals and charters, (with the exception of red wine, which is prohibited due to the high potential for staining the deck). It is wise to stay hydrated with non-alcoholic beverages. We offer bottled water for sale at our facility. Food is also encouraged and should be confined to items that require little or no on-board preparation. Trail mix bars and small packaged food works the best to keep your energy up throughout the whole class. Class participants often enjoy taking turns bringing treats for the entire group. Any food and beverages that you bring on board for your sail must be disposed of at the end of your reservation. Trash bags can be obtained from the staff in our office and there is a large trash can located on the stern (rear) of our houseboat headquarters.

Chicago Sailing takes safety seriously, including weather related hazards. To that end, we reserve the exclusive right to determine safe sailing conditions. Expect that your class, rental or charter will take place as scheduled unless you hear otherwise from Chicago Sailing. Weather in Chicago can change very quickly and exhibit many different conditions throughout a 12-hour period. You are always welcome to call our Reservations Staff at 773.871.7245 on the day of your sail to obtain an update in regards to the weather. The first day of class will never be canceled, as there is much material that can be taught at the dock regardless of weather conditions.

Weather in Chicago can be suddenly changeable. For this reason we will usually not make a final cancellation or postponement determination until just prior to a scheduled event. Plan to arrive on time unless you are contacted by Chicago Sailing. If you have any weather concerns please call us at 773.871.7245.

On our J/22s there is a small cabin below decks, where your gear can be stowed. While this area is usually dry, we recommend that you lock valuable items in your car. Keep at least one cell phone aboard the vessel in a secure, dry location. We have complimentary watertight bags available at our dock

Punctuality, especially on your first day, is important for many reasons. First, you may experience unexpected delays with traffic or parking. Second, there are important registration forms and procedures that must be completed in order for the class to begin on time. Finally, an early arrival gives you ample time to meet your instructor and fellow students. It is also a good time for a last minute restroom visit. We recommend arriving about 30 min prior to your first class and about 10 min before each subsequent class.

You will receive an email with the basic information needed for the first day of class. Your instructor will hand out textbooks at the end of your first class in preparation for day 2. If you would like to pickup your book before your class begins you may pick it up from our houseboat on Dock B at any time after completing registration.