Go Sailing Chicago - Chicago Sailing Charters - FAQs

what to wear?

Good question! Some days it’s warm and sunny on shore and then suddenly out on the water with wind over the deck, the temperature drops quickly. Before you know it, your favorite t-shirt isn’t cutting it and you’ll have to take out a windbreaker. To accommodate temperature changes, we recommend bringing clothes that layer well and are comfortable while sailing. Basically, check the weather for that day a couple hours before you head out and adjust accordingly.

Footwear. Well, lets put it this way, your high heels may look great while out for dinner but probably aren’t very practical for sailing in Chicago. NO DARK SOLE SHOES may be worn on any of our sailing boats! This is an absolute. If you show with dark sole shoes or high heels you will be asked very politely to remove them before coming aboard.

what NOT to bring?

Please do not bring glass of any kind other than wine bottles, champagne bottles, etc. The “glasses” we provide are acrylic and will not break or shatter if dropped. Also, no illegal substances are allowed while sailing. Footwear. Well, lets put it this way, your high heels may look great while out for dinner but probably aren’t very practical for sailing. We will say it again, your beautiful heels may look great though are not practical for sailing. Please feel to wear flip flops, light soled sneakers, etc. while aboard our Chicago sailing boat.

what is provided during my private charter?

Mostly, we provide a great time on an awesome Chicago sailboat! Beyond that all your flatware, plates, cups, ice, cooler, napkins, etc. will be provided. In addition, a cd/radio/mp3 connection for your listening needs will be onboard and ready for your enjoyment. If you have a lot to keep cool or need extra drink ice please let us know in advance and we will supply extra ice and/or an extra cooler at no charge.

weather. weather? weather! weather!! weather!!!

We are a business that operates in all kinds of weather and we constantly watch conditions. If there is a lack of wind and the sails won’t get us moving, we have our fabulous engine to get us around on our sailing boat. If it’s blowing like crazy and still safe we will go out and offer an exciting sailing experience! We will sail in most conditions including light rain and cold temperatures. Please check out our weather links for up to date information. We do offer rainy day insurance at 10% of the charter rate if purchased 2 weeks or more in advance.

can your charter be cancelled?

Sure can. But let me tell you it’s very rare, and if we do, trust me, you wouldn’t want to be out there anyway! We will cancel a Chicago sailboat charter due to extreme weather conditions such as lightning, huge waves, and constant rain OR extraordinary circumstances. We will do everything to make your charter sail as planned. Please view our cancellation policy.

do i tip my captain?

Yes please! Tipping is customary, and of course, much appreciated by the staff at Go Sailing Chicago. Tips average in the 10-20% percent range and frequently go above and beyond just like our service!

can i be on the mailing list?

Once again, yes! Please email us at info@gosailinchicago.com or let your Captain know that you’d like to be on the mailing list and we will keep you in the loop.

be on time?

Yes please! Although we allow enough time between each sailboat charter and allow for slip-ups, we intend to start and end each trip right on time. This way if you have dinner plans following an afternoon sail, you can be sure you’ll be on time.

what about a bathroom?

Yep, we have that too. At least we did the last time I checked…....... just kidding. Our Chicago charter sailboats are fully equipped with a bathroom and a private room for changing in and out of swimsuits. Let’s Go Sailing Chicago!

can i bring alcohol?

We are such big fans of saying yes that we’ll do it again. Yes! Feel free to bring an adult beverage of your choice during your sailboat charter. Please keep in mind that you are on the water and safety is our top priority, so please drink responsibly. We provide one bag of ice, a cooler, and all the cups you’ll need. Need more? Contact us to let us know your needs for your upcoming sailboat charter and we will do our best to accommodate you and your guests.

can i smoke during my charter?

You may smoke during your sailboat charter if agreeable weather conditions exist and if no other passengers object. Please ask your Captain before lighting up.

can our group go swimming?

Yes again! Granted, on many days the Great Lakes water temperature isn’t conducive to swimming even though the sun may be out shining brightly. On hot days you may want to bring your suit just in case. Go Sailing Chicago!

do i need to make a deposit?

Yes please! We require a 10% deposit on all charters at the time of booking.

how many can come?

6 total guests according to US Coast Guard regulations. We would love to bring more but the law is the law. We will happily refer you to another reputable sailboat charter company that can accommodate more than six passengers. We aim to please at Go Sailing Chicago.

how far in advance should i book my charter?

Wow, you ask really good questions! We suggest you book your sailboat charter as far in advance as possible to make sure you get the time and day you want. Also, please look for our Monday night 2-hour sail special on our special promotions page.