How do I find the boat?
Chicago Sailboat and Yacht Charters boats are located at 31St Street Harbor See the Contact & Directions page on the site.
Where should I park?
Parking is $20-30 per day, taking an Uber is also a great option.
Safety is the number one rule in Boating.
The most dangerous times are leaving the dock and returning so please give us your undivided attention.
What should we wear for our sailing adventure?
Dress for the season and always bring a jacket or an extra layer of clothes. A hat, sunglasses, and sunscreen are also recommended.
Deck shoes or Non-marking shoes are allowed, but we recommend just take off your shoes while on board. Even deck shoes can leave dirt marks on the white surfaces.
Is this sailing trip safe for seniors?
Yes! We help them onboard, and we find a safe place for them to stay seated during the trip.
Can children come on the charter?
Yes, we love kids and they love to sail! Children under the age of 13, including infants, are required by law to wear a life jacket.
Do I need to bring a lifejacket?
Lifejackets will be provided for all passengers. If you are bringing children please let us know the ages and sizes you will need. If you have very young children please bring a lifejacket that you are sure fits them properly.
We have plenty of them on board and they can be found under the stairs going down to the cabin. If you take one out to go swimming make sure you bring it back to the boat.
How early should I arrive for my sailing excursion?
Please arrive at least 15-30 minutes before your scheduled excursion. Sign in with a crewmember before boarding the vessel.
Can I drive the yacht?
Yes, you can be as hands-on as you like once the captain is out of the harbor. You can help raise and trim the sails as well. Of course, the captain is always in charge.
How long are the sailing trips?
From 3 hours or the entire day
Are there restrooms on the boats?
Yes! There are rules to the restrooms (head). Here they are:
Number 1’s, totally cool!
Number 2’s not so cool! Please try to plan accordingly
We have instructions on how to use the head on the wall of the bathroom.
How far out do we go on the sailing adventures?
It depends on the adventure you book. We can stay along the shore or sail out several miles.
Personal items – Don’t lose them
Phones, wallets, purses & cameras, please leave them in the cabin, they don’t float. We have a phone charging cable in the cabin on the table to the right of the stairs.
How many people can come?
Due to Coast Guard Regulations, we can only carry up to 12 passengers at a time.
Can I book an overnight trip on a yacht?
Yes. You can book for overnight stays, just contact us about the dates you are interested in.
Who will be sailing the yachts?
A licensed and certified USCG captain and crew will be in charge of all charters.
Can we swim off the boat?
Swimming is permitted when the boat is anchored. Stay directly off the back of the boat so we can see you at all times. We have a ladder on the back of the boat. It’s always a good idea to bring along a life preserver with you. Don’t swim if you have drank a bit too much.
Don’t know how to swim?
Please let us know and wear a Life preserver or at least keep it very close to you.
Do I need to bring towels?
Yes, if you plan to go swimming.
Can we bring food and drink on board?
Yes, please bring food, snacks, soft drinks, beer and white wine. If you’re planning a party that will require catering, you can either arrange your own, or talk to us, and we can arrange catering and party amenities for you, at an additional cost.
No over drinking
Eat food all day. Drink plenty of water.
Use the buddy system, don’t let friends drink too much and try to swim it does not work. If the captain see anyone being over-served we will first ask them to stop drinking and if they continue we will cancel the rest of the trip and head back to shore.
No red wine, please
It stains things; please don’t bring it on board
Will my cell phone work on the lake?
Yes, cell phones work on the lake anywhere within 5-10 miles of shore.
Will I get seasick?
Some people experience seasickness however if you are prone to it, we recommend taking motion sickness medication in advance of the trip as directed. Taking the medicine once you start feeling sick will not help.
Do you supply a cooler on board?
Yes, we have a cooler on board. If you need to bring a cooler onboard we recommend soft-sided ones.
Can we bring our dog(s)?
No, We love our furry friends but more times than not we enjoy the sailing experience more than they do.
What happens if the weather is bad and Cancellations?
We must respect Mother Nature and will not put anyone in danger. If it’s raining, lightning, hailing or just too rough to sail we will reschedule your group for a future date or provide a full refund. The weather in Chicago can change in a flash so we typically wait until the last minute to cancel a charter. We keep an eye on the NOAA Radar website. Click this link and you can view the same weather radar data we use.
Just think about how few baseball games are canceled due to rain, we may get delayed a little while but 95% of the time we go out and have a wonderful time.
How do I reserve a boating adventure?
Reserve your adventure online
What about gratuity?
It is customary to tip your captain and crew at the end of a great voyage. If you enjoyed your sail, let them know. 10 -20% is standard.