CHICAGO'S PREMIER ​SAILING EXPERIENCE ​AND PRIVATE SAILING CHARTER

SEMI-PRIVATE CHARTERS CANCELLED FOR 2021
Click for details

We are excited to introduce our latest offering in charter sailing services -- the Semi-Private Shared Sail!  Instead of paying for an entire private charter, you simply pay per passenger.  (Perfect for a couple that wants to enjoy a sunset sail!)  A unique feature of this new lower-priced option is that you will be sharing the sail with up to 5 other passengers, but the total number of passengers on board will never exceed six people!

You can rest-assured that you will still receive the excellent service we provide for our private sailing charters:  We still provide a professional captain so that you can kick back and enjoy the ride.  And, as always, you are welcome to participate in the sailing by taking a turn at the helm.

All charters, of any kind, are Non-Smoking and are BYOB.  No glass on board please.

Pro tip: We must have at least 4 passengers in order to run a semi-private charter.  Therefore, when booking your semi-private shared sailing charter, we encourage you to look at dates that already have people booked.

The sailboat that we reserve for your charter will depend on a number of factors including the number of guests, availability of sailboats, conditions on the lake, etc.  We will allocate either our Catalina 36 sailboat (s/v Bernard) or our Shannon 28 sailboat (s/v Druid).  Trust us, both of these boats are a blast to sail.  However, if you prefer to sail aboard a particular sailboat of your choosing, then we encourage you to consider one of our private charters instead.

Sailing Chicago's beautiful lakefront offers an experience not to be missed and views of the skyline that can't be beat. Kick back and let our experienced crew treat you to a relaxing sail along Chicago's beautiful lakefront.

Checkout our CUSTOM CHARTERS for options like EXTENDED SAILING TIMES, SWIMMING, and GRILLING.

​​Come Sailing is Chicago's premier sailing experience and private sailing charter offering a variety of boat rides, sailing charters, sightseeing tours, swimming trips, and customized private charters on Lake Michigan.  Take a break, Come Sailing, and enjoy some summer ​fun in the sun!

Your Chicago sailing and offshore adventures start here!

Sunset Sail

FOR DETAILS / BOOKING
CHOOSE CHARTER TYPE

SHARED

PRIVATE

CANCELLED
Shared
​Semi-Private Charters

This is a semi-private sailing experience.
You will be sailing with other passengers..

FEATURES

• Max of 6 Passengers per Charter
• Two-hour Charter *
• ​Departs @ 11:00 AM, 1:30 PM, 4:00 PM
• USCG Licensed Captain

* Extend your time on the water with a
CUSTOM CHARTER

CANCELLED
​Fireworks

FOR DETAILS / BOOKING
CHOOSE CHARTER TYPE

SHARED

PRIVATE

STEP 1 - A SAILBOAT WILL BE SELECTED FOR YOUR CHARTER

BOOK SEMI-PRIVATE CHARTER

Sailing Vessel Bernard
​
Our 36 ft. Sailboat built by Catalina Yachts

$98​/person

WEEKDAYS
(Monday thru Thursday)
​Taxes are additional

$112​/person

WEEKENDS
(Friday thru Sunday)
Taxes are additional

FEATURES

• Instant booking confirmation.​
• Spacious design with plenty of room for 6 passengers.
• Large cockpit area with comfortable seat cushions.
• Additional seating on sizable forward deck.
• Swimming options available.
• Options available for use of gas grill.
• See more details on s/v Bernard​

​

Sailing Vessel Druid

Our 28 ft. Sailboat built by Shannon Boat Co.

$98​/person

WEEKDAYS
(Monday thru Thursday)
​Taxes are additional

$112​/person

WEEKENDS
(Friday thru Sunday)
Taxes are additional

FEATURES

• Classically charming sailboat.​
• Luxuriously adorned with elegant teak.
• Comfortable seat cushions
• Additional seating built into aft cockpit rail.
• Sporty sailing characteristic with a bit of heel (lean).
• Room for 6, but most comfortable with 4 passengers.
• See more details about s/v Druid

​

BOOK SEMI-PRIVATE CHARTER