What to wear?

Good question! Some days it’s warm and sunny on the Chicago 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 while sailing, we recommend bringing clothes that layer well and are comfortable. Basically, check the weather for the day a few hours before you head out for your sailboat charter or sailing lesson 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. If you show with dark sole shoes for a sailing lesson or Helm Time session, you will not be allowed to participate.

What is provided during my private sailboat 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 player/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.

Please do not bring glass of any kind other than wine bottles, champagne bottles, etc. for your charter. The “glasses” we provide are acrylic and will not break or shatter if dropped. Also, no illegal substances are allowed while sailing. Footwear - we will say it again, your beautiful heels may look great though are not practical for sailing. No dark soled shoes may be worn onboard. Please feel free to wear flip flops, light soled sneakers, etc. while aboard a sailing charter.

Weather. Weather? Weather! Weather!! Weather!!!

We are a sailing 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 sailboats. 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 sporadic light rain, wavy, very windy, and cold temperatures. 

Can your sailboat charter, sailing lesson, or Helm Time session 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, sailing lesson, or Helm Time session due to extreme weather conditions such as lightning, huge waves, and constant rain (lessons will go out in rain if not pouring down) OR extraordinary circumstances. We will do everything to make your sailing adventure goes as planned. 

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!

Be on time?

Yes please! Although we allow enough time between each sailboat charter and lesson to 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 sailboat charters and instruction sailboats are fully equipped with bathrooms. 

Can i bring alcohol on a sailboat charter or lesson?

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.  Alcohol is NOT allowed during sailing lessons or Helm Time.

PLEASE NOTE: alcohol is not allowed during sailing lessons or Helm Time sessions.

Can i smoke during my sailboat charter, sailing lessons, or Helm Time sessions?

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. Smoking is not allowed during sailing lessons, Helm Time sessions, or on Obsession at any time. 

Can our group go swimming on private charters?

On many days the water temperature on Lake Michigan isn’t conducive to swimming even though the sun may be out and shining brightly. On hot days you may want to bring your suit just in case. No swimming is allowed on Mystify or Obsession regardless of weather.

How far in advance should I book my sailboat charter, sailing lesson, or Helm Time session?

Wow, you ask really good questions! We suggest you book your sailboat charter, sailing lesson, or Helm Time session as far in advance as possible to make sure you get the time and day you want. Don’t forget you can text us your reservation request to 773.710.7245 (SAIL).

How many students are in one sailing lesson course or in a Helm Time session?

We purposefully keep course sizes to a maximum of 4 students. This way each student will receive maximum exposure and experience to each position on the boat. For Helm Time sessions, we max out at 6 like we do for charters. We man each Helm Time session with an instructor but allow the students to truly guide the experience. After all it’s about getting in some on the water time, refining your skills, and having fun!

How many guests can come on private sailboat charters?

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 on one boat. We aim to please at Go Sailing Chicago!